Home Vacation Rentals By Owner In Chicago, IL

Showing 2420 Of 2640 Vacation Rentals
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Exceptional(1)

$199.0

/ Nightly
Condo

Chicago Cityview Chic - Gold Coast/River North

Chicago, Illinois, United States

Welcome to our stylish, modern 2-bed, 1-bath condo located in the vibrant Gold Coast/River North neighborhood. Discover the epitome of comfort and convenience with our outstanding amenities, unbeatable location, breathtaking city view, and dedicated workspace, making our condo the ideal choice for your unforgettable Chicago stay.brbrStep into our fully remodeled condo and be greeted by a tastefully decorated living space featuring a cozy fireplace, comfortable seating, and a large flat-screen TV with cable. Prepare to be captivated by the awe-inspiring views of the city, located in the northwest corner.brbrThe fully equipped kitchen features quartz countertops with modern appliances, including a Keurig and a new electric stove with a built-in air fryer. It's perfect for preparing meals, with extras like a toaster, panini maker, and blender. Enjoy your meals in the cozy dining area, or explore nearby restaurants and coffee shops.brbrOur condo is tailored for maximum comfort, comfortably hosting up to four guests across two bedrooms, each equipped with Smart TVs. The primary bedroom elevates your stay with a fireplace, adding a touch of luxury and warmth to your experience. For those working from home, we provide a dedicated workspace in the primary bedroom complete with a monitor, docking station, mouse, keyboard, and WiFi. Additionally, the bathroom has been fully remodeled, boasting a sleek, modern design.brbrNestled in a desirable location, our condo is blocks away from several acclaimed restaurants, bustling shopping districts, and highly sought-after attractions. Indulge in world-class shopping on Michigan Avenue, take in the breathtaking views from the John Hancock Observatory, or soak up the sun on the pristine shores of Oak Street Beach. For those working in the medical field or seeking medical services, Northwestern Memorial Hospital and Lurie Children's Hospital are located conveniently within walking distance. Convenient parking is available in the building for an additional fee.brbrExperience the perfect blend of modern comfort, stunning views, and an unbeatable location. Book your stay today for an unforgettable Chicago experience!brbrPLEASE NOTE: No animals are permitted on the property. Due to the host’s family being allergic to animal hair and dander, the listing is strictly allergy-free.
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Bath 1

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Sleep 4

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$1399.0

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Private Vacation Home

Wicker Park 4BD Home: Parking, Theater, & Rooftop

Chicago, Illinois, United States

Summary:brbrWelcome to TheDreamRentals opulent 4-bedroom sanctuary! brbrbrbr- Chef's kitchen with top-of-the-line appliances brbr- Four luxurious bedrooms and three bathroomsbrbr- State-of-the-art home theater for cinematic experiences brbr- Two rooftop patio decks for outdoor loungingbrbr- Two car garage - rare find in Chicagobrbr- Close to the best restaurants and cafesbrbrbrbrBook your stay with TheDreamRentals today!brbrbrbrThe Space:brbrWelcome to TheDreamRentals opulent 4-bedroom sanctuary, where luxury meets entertainment in the heart of the city! Nestled in an upscale neighborhood, this exquisite home boasts not only a full-fledged theater but also two stunning rooftop patio decks, making it the perfect choice for your upscale getaway. brbrbrbrComfortable Accommodation:brbr- Four meticulously designed bedrooms brbr- Master suite with a king-sized bed and sofa bedbrbr- Second bedroom with queen size bed and sofa bedbrbr- Third bedroom with queen bed and a full over full bunk bedbrbr- Kids bedroom with three single bedbrbrbrbrInterior Feeling:brbr- Spacious living areas brbr- Elegant decor and plush furnishings brbrbrbrEntertainment Oasis:brbr- State-of-the-art home theater brbr- Massive screen for cinematic experiences brbr- Comfortable seating for movie nights and private screenings brbrbrbrOutdoor Bliss:brbr- Two rooftop patio decks brbr- Ideal for lounging, dining, or sipping cocktails brbr- Perfect for sunbathing or stargazing brbrbrbrDelightful Dining:brbr- Chef's dream kitchen brbr- Top-of-the-line appliances brbr- Granite countertops brbrbrbrProfessional Cleaning:brbr- Immaculate cleanliness maintained throughout the property brbrbrbrBook with us today and enjoy exclusive discounts with our trusted local vendors! Elevate your stay with special rates on limo services, private yacht charters, helicopter rides, kayak rentals, outdoor sauna experiences, private chefs, and so much more. Let us help you create an unforgettable experience from start to finish!brbrbrbrGuest Access:brbrGuests will have access to the entire home during their stay!brbrbrbrThe Neighborhood:brbrWelcome to the eclectic and vibrant neighborhood of Wicker Park in Chicago. Known for its artistic spirit, historic charm, and a unique blend of cultures, Wicker Park offers an unforgettable urban experience. Here's a glimpse of what makes this neighborhood special:brbrbrbr1. Arts and Culture: Wicker Park is a hub for creativity and artistic expression. You'll find a plethora of art galleries, street murals, and theaters showcasing local talent. The neighborhood's bohemian atmosphere is a testament to its commitment to the arts.brbrbrbr2. Dining and Culinary Scene: Food enthusiasts will be in culinary heaven in Wicker Park. The neighborhood boasts a diverse array of restaurants, cafes, and eateries serving up everything from gourmet cuisine to classic comfort food. Try out trendy brunch spots, international flavors, and local delicacies.brbrbrbr3. Boutique Shopping: Explore the neighborhood's trendy boutiques and vintage shops, perfect for fashion-forward individuals looking for unique clothing, accessories, and home decor. Wicker Park is a fashion destination where you can discover one-of-a-kind treasures.brbrbrbr4. Entertainment and Nightlife: When the sun goes down, Wicker Park comes alive with its energetic nightlife. Dive into the local bar scene, catch live music at intimate venues, or dance the night away at lively clubs. The neighborhood is known for its diverse music and nightlife options.brbrbrbr5. Green Spaces: Relax and recharge in the neighborhood's parks and green spaces. Wicker Park itself offers a beautiful park with walking trails, a playground, and a relaxing atmosphere. It's an ideal spot for picnics and outdoor activities.brbrbrbr6. Hipster Haven: Wicker Park has a distinct hipster vibe, attracting a diverse community of artists, musicians, and creative individuals. This unique blend of cultures creates a welcoming and open-minded atmosphere.brbrbrbr7. Festivals and Events: Throughout the year, the neighborhood hosts various festivals and events celebrating music, arts, and culture. These events provide an opportunity to immerse yourself in the local scene and connect with the community.brbrbrbr8. Public Transit: Wicker Park's central location in Chicago provides excellent access to public transportation, including CTA buses and the Blue Line, making it easy to explore other parts of the city.brbrbrbr9. Historic Architecture: The neighborhood is known for its historic buildings and charming architecture, showcasing a mix of Victorian-era mansions and contemporary developments.brbrbrbrWicker Park is a neighborhood that celebrates individuality, creativity, and community. Whether you're an art lover, a foodie, a music enthusiast, or simply looking to soak in the neighborhood's unique ambiance, Wicker Park offers an exciting and dynamic urban experience that you won't soon forget. Come explore the streets and alleys of this vibrant Chicago gem.brbrbrbrGetting Around:brbrWicker Park is a well-connected neighborhood in Chicago, making it easy for visitors to explore both within the neighborhood and beyond. Here's a guide to getting around in Wicker Park:brbrbrbr1. Walking: Wicker Park is a pedestrian-friendly neighborhood with tree-lined streets and plenty of interesting shops, restaurants, and cultural attractions within easy walking distance. Stroll through the streets to soak in the local vibe and discover hidden gems.brbrbrbr2. Public Transit: Chicago's public transportation system, operated by the Chicago Transit Authority (CTA), provides convenient access to Wicker Park. The following options are available:brbrbrbrCTA Blue Line: The Blue Line 'L' train serves Wicker Park with the Damen and Division stations. This line connects you to downtown Chicago, O'Hare International Airport, and other key areas in the city.brbrbrbrBus Routes: Several CTA bus routes run through or near Wicker Park, offering additional transportation options for exploring different parts of Chicago.brbrbrbr3. Biking: Wicker Park is a bike-friendly neighborhood with dedicated bike lanes and bike-sharing programs. You can easily rent a bike and explore the area at your own pace, taking advantage of the bike-friendly streets and paths.brbrbrbr4. Ridesharing Services: Ride-hailing services like Uber and Lyft are widely available in Wicker Park, providing convenient and on-demand transportation to any destination in the city.brbrbrbr5. Divvy Bike Share: Chicago's Divvy bike-sharing program has stations throughout Wicker Park, allowing you to rent bicycles for short trips and explore the neighborhood and surrounding areas.brbrbrbr6. Car Rentals: While parking can be challenging in some parts of Wicker Park, if you plan to explore the broader Chicago area, car rentals are readily available from several agencies.brbrbrbr7. Taxis: Traditional taxi services are also accessible in Wicker Park, and you can easily flag down a cab or request one from a designated taxi stand.brbrbrbr8. Scooter Rentals: In recent years, electric scooter-sharing services have become popular in Chicago, including Wicker Park. You can rent electric scooters for short trips within the neighborhood.brbrbrbr9. Walking Tours: Consider joining a guided walking tour of Wicker Park to get insider knowledge about the neighborhood's history, art, and culture while exploring on foot.brbrbrbrNavigating Wicker Park and the surrounding areas is convenient, with various transportation options at your disposal. Whether you prefer public transit, walking, biking, or ridesharing, you'll have no trouble getting around and experiencing all that this vibrant Chicago neighborhood has to offer.brbrbrbrOther Things to Note:brbrCheck-In/Check-Out: Standard check-in time is at 4:00 PM, and check-out is at 11:00 AM. If you require early check-in or late check-out, please let us know, and we'll do our best to accommodate your request.brbrbrbrHouse Rules: We kindly request that you respect our house rules, which will be provided upon booking confirmation. These rules are in place to ensure a pleasant stay for all guests.brbrbrbrCleaning and Maintenance: The property is professionally cleaned and maintained to the highest standards before your arrival. If you need additional cleaning or have maintenance concerns during your stay, our team is just a phone call away.brbrbrbrPets and Smoking: Regrettably, we do not allow pets on the property, and smoking is strictly prohibited indoors. If you wish to smoke, please do so on the outdoor patio areas while being mindful of other guests and disposing of cigarette butts responsibly.brbrbrbrSecurity: To abide by all legal requirements and building security rules, you will be asked to provide a copy of your official government-issued photo ID, confirm your contact information, provide a valid credit card with a name that matches your ID, and pass through our verification portal. Security deposit of $500 will be required before check in.brbrbrbrShared Housing Unit Operation License Number: 2823378 brbrChicago Registration Number: R21000073252
Bed 4

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Bath 3

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Sleep 17

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$819.54

/ Nightly
Apartment

Downtown 3BD 3BA Condo|Parking, Pool, Gym, Rooftop

Chicago, Illinois, United States

Summary:brbrWelcome to your spacious urban getaway in Chicago’s Printer’s Row! brbrbrbr- Modern 3-bedroom, 3-bathroom unit with floor-to-ceiling windows brbr- Bright, open-concept living space with smart TV and high-speed Wi-Fi brbr- Access to fitness center, rooftop pool, and panoramic deck brbr- Stunning city views perfect for sunset drinks brbr- 1 parking spot available for sedans and small SUVs brbrbrbrBook your stay with TheDreamRentals today!brbrbrbrThe Space:brbrWelcome to your spacious urban getaway in the heart of Chicago’s iconic Printer’s Row neighborhood! This modern 3-bedroom, 3-bathroom unit is located in a stunning high-rise building, offering sweeping city views and access to premium amenities—perfect for families, business travelers, or groups looking to explore the best of downtown. brbrbrbrComfortable Accommodation: brbr- 3 bedrooms with full-sized beds brbr- Plush bedding for a restful night's sleep brbr- Ample closet space for your belongings brbr- 3 bathrooms for convenience brbrbrbrInterior Feeling: brbr- Bright, open-concept living space brbr- Floor-to-ceiling windows providing natural light brbr- Sleek furnishings for a modern touch brbr- Fully equipped kitchen with stainless steel appliances brbr- Granite countertops for a stylish cooking experience brbr- Large living and dining area perfect for relaxation brbr- Smart TV and high-speed Wi-Fi included brbrbrbrOutdoor Bliss: brbr- Rooftop pool (seasonal) for a refreshing dip brbr- Panoramic rooftop deck with unbeatable skyline views brbr- Ideal for sunset drinks or morning coffee brbrbrbrDelightful Dining: brbr- Kitchen equipped for cooking and dining in style brbr- Nearby charming cafes and restaurants brbrbrbrProfessional Cleaning: brbr- Regular cleaning to ensure a pristine environment brbr- Secure entry and elevator access for safety brbrbrbrParking: brbr- 1 parking spot available brbr- Suitable for sedans and small SUVs only brbrbrbrBook with us today and enjoy exclusive discounts with our trusted local vendors! Elevate your stay with special rates on limo services, private yacht charters, helicopter rides, kayak rentals, outdoor sauna experiences, private chefs, and so much more. Let us help you create an unforgettable experience from start to finish!brbrbrbrGuest Access:brbrGuests will have access to the unit and all the amenity floorsbrbrbrbrThe Neighborhood:brbrPrinter’s Row is ideally located just a short walk from many of Chicago’s top attractions—only 5 to 10 minutes from Grant Park, Millennium Park, and the Art Institute of Chicago. It’s also close to the Museum Campus, including the Field Museum and Shedd Aquarium, which are about 20–25 minutes away on foot or a quick bus ride. The neighborhood is within walking distance of the Willis Tower and the Loop’s shopping, dining, and theatre district, making it a perfect home base for exploring the city while enjoying a quieter, more residential atmosphere.brbrbrbrGetting Around:brbrIt is exceptionally well-connected for getting around Chicago by public transportation. It’s just a short walk to several major CTA train stations, including Harold Washington Library (serving multiple lines), LaSalle (Blue Line), and Jackson (Red and Blue Lines), making travel across the city easy and fast. The LaSalle Street Metra station is right around the corner for suburban commuters, and Union Station is about 15–20 minutes away on foot. Several CTA bus routes run nearby on State, Clark, and Dearborn, and Divvy bike stations are close by for quick, flexible trips. Overall, it’s a prime spot for car-free living with easy access to everything downtown and beyond.brbrbrbrOther Things to Note:brbrWe're thrilled to welcome you to our amazing home, where luxury and comfort intertwine to create an unforgettable experience. To ensure your stay is as seamless and enjoyable as possible, here are some additional details to keep in mind:brbrbrbrCheck-In and Check-Out: Check-in time is 4:00 PM, and check-out time is 11:00 AM. If you require early check-in or late check-out, please let us know in advance, and we'll do our best to accommodate your request. brbrbrbrNo Smoking: For the comfort of all guests, smoking is strictly prohibited within the penthouse. Please smoke outside. brbrbrbrPet Policy: We adore pets, but unfortunately, the house is not pet-friendly. We appreciate your understanding in adhering to this policy. brbrbrbrQuiet Enjoyment: Respect for fellow residents and neighbors is paramount. Please keep noise levels at a considerate level, especially during quiet hours, to maintain a peaceful environment. brbrbrbrMaximum Occupancy: The maximum number of guests allowed in the home is as indicated in your booking details. Hosting additional overnight guests without prior approval is not permitted. brbrbrbrMonitoring: We have camera's outside of the building. It will be recording during the reservations. Tampering with these will result in a fine.brbrbrbrSecurity: To abide by all legal requirements and building security rules, you will be asked to provide a copy of your official government-issued photo ID, confirm your contact information, provide a valid credit card with a name that matches your ID, and pass through our verification portal. Security deposit of $500 will be required before check in.brbrbrbrShared Housing Unit Operation License Number: 2823378brbrChicago Registration Number: R25000128701brbrbrbrInteraction with Guests:brbrSupport at Your Fingertips: Should you have any questions, need recommendations, or encounter any issues during your stay, feel free to reach out to us. We're just a message or call away and are dedicated to ensuring your comfort.brbrbrbrFeedback Welcomed: We value your feedback and would love to hear about your experience. If there's anything we can do to enhance your stay or if you have suggestions for improvement, please don't hesitate to share. Our goal is to strike the perfect balance between being available to meet your needs and respecting your desire for a tranquil and enjoyable stay.
Bed 3

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Bath 3

Bath

Sleep 6

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Exceptional(2)

$718.64

/ Nightly
Apartment

United Center 3BD Apt with Parking and Balcony

Chicago, Illinois, United States

Summary:brbrWelcome to our stylish 3-bedroom, 2-bath condo just steps from the United Center! brbrbrbr- Modern space with open-concept living area brbr- Abundant natural light and city views brbr- Fully equipped kitchen and private balcony brbr- Spacious bedrooms with luxurious linens brbr- In-unit laundry and high-speed WiFi brbr- Smart TVs for entertainment brbrbrbrBook your stay with TheDreamRentals today!brbrbrbrThe Space:brbrThe open-concept living area welcomes you with its abundance of natural light and stylish furnishings. The expansive windows not only fill the space with warmth and brightness but also offer breathtaking views of the surrounding cityscape. Sink into the plush sofa and unwind after a day of exploration, or gather with loved ones to plan your next adventure. A large flat-screen TV for your entertainment needs ensures you never miss your favorite shows.brbrbrbrComfortable Accommodation: brbr- Three spacious and thoughtfully designed bedrooms brbr- Master bedroom with a comfortable king sized bed brbr- Luxurious linens for a restful night's sleep brbr- Ensuite bathroom for added privacy and convenience brbr- Second and third bedrooms also feature cozy queen-sized beds brbr- Second bathroom nearby equipped with essentials brbrbrbrInterior Feeling: brbr- Open-concept living area filled with natural light brbr- Stylish furnishings creating a modern atmosphere brbr- Plush sofa for relaxation brbr- Large flat-screen TV for entertainment brbrbrbrOutdoor Bliss: brbr- Private balcony for fresh air and city views brbr- Perfect spot for morning coffee or evening relaxation brbrbrbrDelightful Dining: brbr- Fully equipped kitchen with sleek countertops brbr- Modern appliances for easy meal preparation brbr- Ample storage space for all your cooking needs brbrbrbrProfessional Cleaning: brbr- Meticulously cleaned and maintained for your comfort brbrbrbrBook with us today and enjoy exclusive discounts with our trusted local vendors! Elevate your stay with special rates on limo services, private yacht charters, helicopter rides, kayak rentals, outdoor sauna experiences, private chefs, and so much more. Let us help you create an unforgettable experience from start to finish!brbrbrbrGuest Access:brbrGuests will have access to the entire condo including an in unit washer/dryer and one parking spot in the back of the building.brbrbrbrThe Neighborhood:brbrWest Town is one of Chicago’s most vibrant and evolving neighborhoods, known for its mix of historic charm and modern energy. Tree-lined streets are filled with classic brick walk-ups, trendy cafes, local boutiques, and some of the city’s best restaurants and nightlife. The area includes popular pockets like Wicker Park and Ukrainian Village, offering a creative, artsy atmosphere with plenty to explore just steps from your door. Guests love West Town for its easy access to downtown Chicago, nearby public transportation, and its perfect balance of residential comfort and urban excitement.brbrbrbrGetting Around:brbrIt is convenient whether you’re arriving by plane, car, or public transit. From O'Hare International Airport (about 30–40 minutes by car), guests can take a taxi or rideshare directly to the property, or hop on the CTA Blue Line toward downtown and transfer to a bus or rideshare for the final stretch. From Midway International Airport (about 25–30 minutes by car), rideshare is the quickest option, or take the Orange Line downtown and connect to a bus heading west. If driving, the home is easily accessible from I-290 (Eisenhower Expressway). For those using public transportation, several CTA bus routes run along Washington Boulevard and nearby major streets, with quick connections to downtown and surrounding neighborhoods.brbrbrbrOther Things to Note:brbrCheck-In and Check-Out: Check-in time is 4:00 PM, and check-out time is 11:00 AM. If you require early check-in or late check-out, please let us know in advance, and we'll do our best to accommodate your request.brbrbrbrNo Smoking: For the comfort of all guests, smoking is strictly prohibited within our property or on the balcony.brbrbrbrPet Policy: We adore pets, but unfortunately, the house is not pet-friendly. We appreciate your understanding in adhering to this policy.brbrbrbrQuiet Enjoyment: Respect for fellow residents and neighbors is paramount. Please keep noise levels at a considerate level, especially during quiet hours, to maintain a peaceful environment.brbrbrbrMaximum Occupancy: The maximum number of guests allowed in the home is as indicated in your booking details. Hosting additional overnight guests without prior approval is not permitted.brbrbrbrSecurity: To abide by all legal requirements and building security rules, you will be asked to provide a copy of your official government-issued photo ID, confirm your contact information, provide a valid credit card with a name that matches your ID, and pass through our verification portal. Security deposit of $250 will be required before check in. brbrbrbrMonitoring: We have camera's outside of the home for your safety. It will be recording during the reservations. Tampering with these will result in a fine.brbrbrbrRegistration number: R25000130469brbrbrbrInteraction with Guests:brbrSupport at Your Fingertips: Should you have any questions, need recommendations, or encounter any issues during your stay, feel free to reach out to us. We're just a message or call away and are dedicated to ensuring your comfort. brbrbrbrFeedback Welcomed: We value your feedback and would love to hear about your experience. If there's anything we can do to enhance your stay or if you have suggestions for improvement, please don't hesitate to share. brbrbrbrOur goal is to strike the perfect balance between being available to meet your needs and respecting your desire for a tranquil and enjoyable stay.
Bed 3

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Bath 2

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Sleep 6

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$1683.25

/ Nightly
Private Vacation Home

Designer Oasis - Sauna, Hot Tub, Patios, Game room

Chicago, Illinois, United States

Summary:brbrWelcome to your stylish 5BR oasis in Wicker Park! brbrbrbr- Beautifully designed interiors blend modern aesthetics with cozy touches. brbr- Spacious atmosphere ideal for families, friends, or business travelers. brbr- Three outdoor patios with seating, plus a sauna and hot tub. brbr- Entertainment basement with air hockey and foosball tables. brbr- Prime location near trendy shops, restaurants, and nightlife. brbrbrbrBook your stay with TheDreamRentals today!brbrbrbrThe Space:brbrSpacious 5-Bedroom Retreat with 3 Outdoor Patios in Wicker Park, Chicago. This stunning 5-bedroom, 3.5-bathroom home offers the perfect mix of style, comfort, and entertainment for your stay. Whether you're traveling with family, friends, or a large group, there's plenty of space to unwind and enjoy.brbrbrbrComfortable Accommodation: brbr- Five spacious bedrooms brbr- Comfortable beds with luxury linens brbr- 3.5 modern bathrooms brbr- Clean, bright, and well-appointed with high-end finishes brbrbrbrInterior Feeling: brbr- Beautifully designed interiors brbr- Blending modern aesthetics with cozy touches brbr- Welcoming atmosphere brbrbrbrOutdoor Bliss: brbr- Three outdoor patio areas brbr- Relax and soak up the sun brbr- Enjoy a morning coffee on beautiful patios brbr- Backyard features a sauna and hot tub brbrbrbrDelightful Dining: brbr- Ample dining space for group meals brbr- Easy access to nearby trendy restaurants brbrbrbrEntertainment Options: brbr- Entertainment basement with a game room brbr- Air hockey table and foosball table brbr- Perfect for friendly competition brbrbrbrProfessional Cleaning: brbr- Thoroughly cleaned and maintained brbr- Fresh towels and toiletries provided brbrbrbrPrime Location in Wicker Park: brbr- Steps away from trendy shops and nightlife brbr- Easy access to public transportation and downtown Chicago brbrbrbrBook with us today and enjoy exclusive discounts with our trusted local vendors! Elevate your stay with special rates on limo services, private yacht charters, helicopter rides, kayak rentals, outdoor sauna experiences, private chefs, and so much more. Let us help you create an unforgettable experience from start to finish!brbrbrbrGuest Access:brbrThis is our family home, not a full-time rental. We're happy to share it with guests and simply ask that you treat it with the same care and respect you would your own home. You’ll find personal items throughout the house, we kindly ask that you leave them as you found them. If anything is accidentally damaged or broken, please let us know right away. We completely understand that accidents happen, and early communication allows us to handle things smoothly and respectfully.brbrbrbrMake yourself at home, the entire space is yours to enjoy during your stay!brbrbrbrThe Neighborhood:brbrWicker Park is a vibrant and trendy neighborhood in Chicago, known for its mix of historic architecture and modern developments. It’s home to a thriving arts scene, with numerous galleries, live music venues, and independent shops. The area boasts a diverse dining scene, from casual eateries to upscale restaurants, alongside cozy cafes and lively bars. Wicker Park is also known for its green spaces, including the popular Wicker Park itself, perfect for outdoor activities. With easy access to public transit, it offers a dynamic blend of urban living and artistic energybrbrbrbrGetting Around:brbrWhether you're heading downtown or to other parts of the city, public transportation is easily accessible from this location.brbrbrbrOther Things to Note:brbrParking: There is a garage that can fit two cars. Street parking is available nearby. Please check for local signage and restrictions to avoid any fines or towing. Please note that there is a Vespa scooter stored in the garage. It is NOT available for guest use, but we kindly ask that you treat it with care and avoid moving or handling it. Parking in the handicap spot is strictly prohibited.brbrbrbrStairs: The home has multiple levels, including a basement and second-floor bedrooms. If anyone in your group has mobility concerns, please keep this in mind.brbrbrbrNoise: This is a residential area, so we kindly ask that you keep noise levels respectful, especially after 9 PM. We want you to enjoy your stay, but we also ask that you help us maintain a good relationship with our neighbors.brbrbrbrOutdoor Spaces: Chicago’s weather can be unpredictable, so while we have outdoor seating available year-round, please note that the patios may not always be usable during extreme weather conditions.brbrbrbrCleaning: We provide professional cleaning between stays to ensure a spotless and comfortable environment. However, for longer stays, additional cleaning services can be arranged upon request for an extra fee.brbrbrbrCheck-out: Our standard check-out time is 11 AM, and while we strive to accommodate early check-ins and late check-outs when possible, these are subject to availability. Please let us know in advance if you need special arrangements.brbrbrbrSecurity: To abide by all legal requirements and building security rules, you will be asked to provide a copy of your official government-issued photo ID, confirm your contact information, provide a valid credit card with a name that matches your ID, and pass through our verification portal. Security deposit of $500 will be required before check in.brbrbrbrRegistration number: R2500133858brbrShared Housing Unit Operation License Number: 2823378brbrbrbrInteraction with Guests:brbrWe have no preferences on interaction with guests. We offer self check-in but we can be as interactive as you would like. We are a phone call, text, or blocks away.
Bed 5

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Bath 4

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Sleep 16

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Exceptional(11)

$1040.9

/ Nightly
Apartment

The Cornerstone - Designer 4BR Flat in Bucktown/WP

Chicago, Illinois, United States

Summary:brbrWe invite you to spend your next trip in this beautifully remodeled flat in Chicago's iconic Wicker Park neighborhood. Situated at the intersection of Milwaukee/Damen/North, the location couldn't possibly be better. Countless trendy dining options, bars, shops, and more are just steps away, as well as the Damen Blue Line 'L' station, which links you directly to O'Hare in ~32 minutes. This space was created by celebrity designer Erik Kolacz, featured on Bravo's Top Design.brbrbrbrThe Space:brbrA DESIGN-LOVER'S DREAMbrbrThis private four-bedroom, two-bathroom apartment was artfully designed with a modern aesthetic combined with a few quirky details, creating a chic yet whimsical vibe. brbrbrbrInside the flat you'll find:brbr• Four unique bedrooms, all furnished with comfy queen-sized beds.brbr• Two spacious bathrooms with spa-style stand up showers and EO bath products.brbr• In-unit laundry room with washer, dryer, iron, and board.brbr• Bright and airy living room with 55 Fire TV (no cable).brbr• Open-concept kitchen with quartz kitchen island, stainless appliances, and an exceedingly-cozy breakfast nook.brbr• High ceilings ranging from 9-15' and luxury LVT flooring throughout.brbrbrbrNO DETAIL OVERLOOKED, BIG OR SMALLbrbrOur team has clocked in an impressive amount of time not only as professional hosts but also as discerning guests. We know hospitality inside and out, and work tirelessly to elevate your stay from average to unforgettable.brbrbrbrEXCLUSIVE PERKSbrbrDuring your stay as our guest, you receive exclusive free access to The Metropolitan, a chic members-only club located on the 66th and 67th floors of the Willis Tower. They have co-working space with gorgeous views overlooking Chicago, a bar with food and drinks all day, a top-notch dining experience at The Craftsman restaurant, and more. Message us for more details!brbrbrbrPARKINGbrbrParking is not included. We highly recommend using a great service called SpotHero to reserve a spot nearby before you arrive.brbrbrbrCHECK-OUTbrbrUnlike many other hosts, we won't ask you to wash the sheets, take out the trash, or mow the lawn. Check-out is at 11am.brbrbrbrGuest Access:brbrYou have private access to the entire 4BR/2BR flat.brbrbrbrInteraction with Guests:brbrNeed more towels Deep dish pizza recommendations We're always on call to answer your questions.
Bed 4

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Bath 2

Bath

Sleep 8

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Exceptional(12)

$1041.32

/ Nightly
Apartment

Luxury Designer Penthouse 3802 | Pool | Gold Coast

Chicago, Illinois, United States

Summary:brbrNEW PENTHOUSE IN THE HEART OF GOLD COAST!brbrbrbrEnjoy your own penthouse in Chicago's Gold Coast-the city's center of nightlife, restaurants, and shopping. Sitting 38 stories in the sky, your 3 bedroom/2 bathroom penthouse offers some of the best views in all of Chicago. The highly secure building includes elevator, rooftop pool, full gym, and is perfect for families traveling to Chicago, professionals visiting the city on work trips, and everything in between. The cityscape views are unbeatable!brbrbrbrThe Space:brbrLocated in a full-service building with elevator access and just steps from Michigan Avenue, your penthouse apartment was professionally designed, sleeping up to 10 people and is perfectly situated for groups, families, and those traveling for work. Everything flows around the spacious and open living room and kitchen which have some of the most breathtaking views of all of Chicago and the Lake, and features high-end cooking appliances and designer level finishes, which creates a unique environment for entertaining and gathering with your group.brbrbrbrYour spacious living/dining room combo is decorated in mid-century modern furniture and features a large sofa (which folds out into another bed), accent chairs, dining table for 8+ people, and smart TV (Netflix, Hulu, Prime, etc. compatible). brbrbrbrAttached to the living area, the high end designer quality chef's kitchen is outfitted with Gaggenau stove, Gaggenau oven, restaurant sized refrigerator and freezer, minifridge, plenty of cabinetry, plates, cups, and cutlery in addition to state-of-the-art kitchen appliances including a Nespresso coffee maker, amongst others.brbrbrbrThis one of a kind apartment comfortably sleeps 10 people and has 3 bedrooms and 2 full bathrooms. The main bedroom with a king bed, full bath. An additional bedroom with a king bed. One additional bedroom featuring a full-over-full bunk bed. brbrbrbrSleeping arrangements/room layout:brbrMain bedroom (bedroom 1): King Bed, full bathroombrbrBedroom 2: King bedbrbrBedroom 3: Bunk Bed (full over full)brbrLiving room: Pull out couchbrbrbrbrWe offer one free parking space in a secured parking garage just a couple blocks away. There are ample parking solutions in the area should you need additional parking and you can park in the lot where we provide the one space for a fee that is paid for at the garage.brbrbrbrOur units are made up fresh before each guest and their group arrives. Our professional cleaning service that we use on all of our properties do a thorough job of cleaning all areas, focusing on high touch point areas. Each bed is stripped and all sheets, pillow covers, and duvet covers are washed thoroughly after each stay.brbrbrbrTo abide by all legal requirements and building security rules, you may be asked to provide a copy of your official government-issued photo ID, confirm your contact information, provide a valid credit card with a name that matches your ID, pass through our verification portal and, in some instances, complete a criminal background check.brbrbrbrImportant note: The information is collected for screening and verification only and is not stored or used for any other purposes.brbrbrbrPlease be advised that all guests will be asked to sign a rental usage agreement that governs the terms of the stay. By completing the reservation you agree to the following:brbrbrbr-You agree to be bound by our rental terms and conditions.brbr-You acknowledge that you will be required to provide a copy of a valid government-issued ID and matching credit card prior to check-in.brbr-You acknowledge that you may be required to undergo a background check if mandated by the property management company or the building, as stated in accordance with your rental agreement and the condition of the booking.brbr-You understand that your check-in instructions might be withheld until you have successfully completed our verification portal.brbrbrbrGuest Access:brbrYou will have full access to all rooms and spaces inside the unit, except for one utility closet. Temporary access codes will be shared 24 hours before rental commencement by email.brbrbrbrInteraction with Guests:brbrWe pride ourselves on making our guest's stay as enjoyable as possible. We live in Chicago and are available should anything come up.
Bed 3

Bed

Bath 2

Bath

Sleep 10

Sleeps

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Exceptional(4)

$1478.21

/ Nightly
Apartment

Luxury Loft Collection COMBO 01/02 | Terrace

Chicago, Illinois, United States

Summary:brbrEnjoy the combination of your own 2 side-by-side private luxury lofts in Chicago's bustling River North-the city's center of main nightlife and restaurants . These two ultra high-end apartments combine for over 5,000 square feet of living and features a private elevator, private terrace, free secured parking, 24 hour doorman, 6 bedrooms/5 full bathrooms, and is perfect for all types of large groups. The cityscape views are unbeatable! is perfect for group trips.brbrbrbrThe Space:brbrOur unique one of a kind lofts are located in Chicago's newest luxury building with views overlooking the city and are the most high-end rental offering in the city. The unit comprised of 2 side-by-side luxury units, joined by elevator, sleeping 28+ people comfortably and is perfectly situated for large groups, families, events, and curated dinners. In each unit, everything flows around the spacious and open living rooms and chef's kitchens, add the floor to ceiling windows with connecting outdoor patio and the space becomes a unique environment for entertaining and gathering with your group.brbrbrbrYour spacious living/dining room combos are decorated in modern contemporary art and features a large sectional, accent chairs, dining areas, smart TV (Netflix, Hulu, Etc. capable) and record player for entertainment.brbrbrbrAttached to each dining room, the chef's kitchens are outfitted with gas-powered Gaggenau ranges, Gaggenau oven and microwave, restaurant sized refrigerator and freezer, plenty of cabinetry, plates, cups, and cutlery in addition to state-of-the-art kitchen appliances including a coffee maker, amongst otherbrbrbrbrIn addition, enjoy your own large private covered terrace with seating and dining options (provided during the nice weather), truly a unique offering and extension of the living area!brbrbrbrThese one of a kind lofts comfortably sleep 22+ people when combined and has 6 bedrooms and 5 full bathrooms. Please note, while we allow 22 people to stay in this unit, there may not be 22 regular beds and allow our guests to figure out their sleeping arrangements.brbrbrbrSleeping arrangements/room layout:brbrBedroom 1: King Bed, bathroom with soaking tub, shower, and heated floorsbrbrBedroom 2: Two full-over-full bunk bed sets, private bathroom with shower brbrBedroom 3: One full-over-full bunk bed and a standard full bed, private bathroom with tub and showerbrbrBedroom 4: King Bed, private bathroom with tub and showerbrbrBedroom 5: Two full-over-full bunks bed, private bathroom with shower and large soaking tubbrbrBedroom 6: Two side-by-side full bedsbrbrbrbrOur units are made up fresh before each guest and their group arrives. Our cleaning services that we use on all of our properties do a thorough job of cleaning all areas, focusing on high touch point areas. Each bed is striped and all sheets, pillow covers, and duvet covers are washed thoroughly after each stay.brbrbrbrTo abide by all legal requirements and building security rules, you may be asked to provide a copy of your official government-issued photo ID, confirm your contact information, provide a valid credit card with a name that matches your ID, pass through our verification portal and, in some instances, complete a criminal background check.brbrbrbrImportant note: The information is collected for screening and verification only and is not stored or used for any other purposes.brbrbrbrPlease be advised that all guests will be asked to sign a rental usage agreement that governs the terms of the stay. By completing the reservation you agree to the following:brbrbrbr-You agree to be bound by our rental terms and conditions.brbr-You acknowledge that you will be required to provide a copy of a valid government-issued ID and matching credit card prior to check-in.brbr-You acknowledge that you may be required to undergo a background check if mandated by the property management company or the building, as stated in accordance with your rental agreement and the condition of the booking.brbr-You understand that your check-in instructions might be withheld until you have successfully completed our verification portal.brbrbrbrGuest Access:brbrYou will have full access to all rooms and spaces inside the unit, except for one utility closet. Temporary access codes will be shared 24 hours before rental commencement by email.brbrbrbrOther Things to Note:brbrOur building is a highly secure building with 24/7 doorman and secure covered parking garage.brbrbrbrInteraction with Guests:brbrWe pride ourselves on making our guest's stay as enjoyable as possible. We live in Chicago and are available should anything come up.
Bed 6

Bed

Bath 6

Bath

Sleep 22

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Exceptional(13)

$1043.46

/ Nightly
Apartment

Luxury Designer Penthouse 3801 | Pool | Gold Coast

Chicago, Illinois, United States

Summary:brbrNEW PENTHOUSE IN THE HEART OF GOLD COAST!brbrbrbrEnjoy your own penthouse in Chicago's Gold Coast-the city's center of nightlife, restaurants, and shopping. Sitting 38 stories in the sky, your 3 bedroom/2 bathroom penthouse offers some of the best views in all of Chicago. The highly secure building includes elevator, rooftop pool, full gym, and is perfect for families traveling to Chicago, professionals visiting the city on work trips, and everything in between. The cityscape views are unbeatable!brbrbrbrThe Space:brbrLocated in a full-service building with elevator access and just steps from Michigan Avenue, your penthouse apartment was professionally designed, sleeping up to 10 people and is perfectly situated for groups, families, and those traveling for work. Everything flows around the spacious and open living room and kitchen which have some of the most breathtaking views of all of Chicago, and features high-end cooking appliances and designer level finishes, which creates a unique environment for entertaining and gathering with your group.brbrbrbrYour spacious living/dining room combo is decorated in mid-century modern furniture and features a large sofa (which folds out into another bed), accent chairs, dining table for 8+ people, and smart TV (Netflix, Hulu, Prime, etc. compatible). brbrbrbrAttached to the living area, the high end designer quality chef's kitchen is outfitted with Viking gas-powered ranges, Viking oven, restaurant sized refrigerator and freezer, minifridge, plenty of cabinetry, plates, cups, and cutlery in addition to state-of-the-art kitchen appliances including a Nespresso coffee maker, amongst others.brbrbrbrThis one of a kind apartment comfortably sleeps 10 people and has 3 bedrooms and 2 full bathrooms. The main bedroom with a king bed, full bath. An additional bedroom with two twin beds side-by-side. One additional bedroom featuring a full-over-full bunk bed. brbrbrbrSleeping arrangements/room layout:brbrMain bedroom (bedroom 1): King Bed, full bathroombrbrBedroom 2: Two Twin Beds side-by-sidebrbrBedroom 3: Bunk Bed (full over full)brbrLiving room: Pull out couchbrbrbrbrWe offer one free parking space in a secured parking garage just a couple blocks away. There are ample parking solutions in the area should you need additional parking and you can park in the lot where we provide the one space for a fee that is paid for at the garage.brbrbrbrOur units are made up fresh before each guest and their group arrives. Our professional cleaning service that we use on all of our properties do a thorough job of cleaning all areas, focusing on high touch point areas. Each bed is stripped and all sheets, pillow covers, and duvet covers are washed thoroughly after each stay.brbrbrbrTo abide by all legal requirements and building security rules, you may be asked to provide a copy of your official government-issued photo ID, confirm your contact information, provide a valid credit card with a name that matches your ID, pass through our verification portal and, in some instances, complete a criminal background check.brbrbrbrImportant note: The information is collected for screening and verification only and is not stored or used for any other purposes.brbrbrbrPlease be advised that all guests will be asked to sign a rental usage agreement that governs the terms of the stay. By completing the reservation you agree to the following:brbrbrbr-You agree to be bound by our rental terms and conditions.brbr-You acknowledge that you will be required to provide a copy of a valid government-issued ID and matching credit card prior to check-in.brbr-You acknowledge that you may be required to undergo a background check if mandated by the property management company or the building, as stated in accordance with your rental agreement and the condition of the booking.brbr-You understand that your check-in instructions might be withheld until you have successfully completed our verification portal.brbrbrbrGuest Access:brbrYou will have full access to all rooms and spaces inside the unit, except for one utility closet. Temporary access codes will be shared 24 hours before rental commencement by email.brbrbrbrInteraction with Guests:brbrWe pride ourselves on making our guest's stay as enjoyable as possible. We live in Chicago and are available should anything come up.
Bed 3

Bed

Bath 2

Bath

Sleep 10

Sleeps

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Exceptional(14)

$1375.72

/ Nightly
Private Vacation Home

Luxe Single Family Home + Private Skyline Rooftop! Sleeps 10

Chicago, Illinois, United States

Perfect for groups and families!brbrWelcome to our gorgeous and modern single family home, there is absolutely no comparison in Chicago.brbrGuests will have access to the entire 3,000 sq ft home over 5 levels. Easy electronic check-in. *NOTE: This is a split level home so expect many stairs*brbr• Prime spot in Ukrainian Village -- walk to West Town or Wicker Park, 10 minute Uber to downtown and Randolph Stbr• 4 bedrooms and 3.5 baths with luxury Beautyrest Black mattresses and Brooklinen linensbr• Huge rooftop deck with outdoor kitchen and skyline viewsbr• State of the art 120 inch home theater + Sonos sound throughoutbr• Fully stocked gourmet kitchen with Wolf, Sub Zero, Miele appliancesbr• Designer RH furniturebr• Peloton bike br• Multiple patiosbr• Blazing fast multi gigabit WiFi, perfect for work or streamingbr• Attached 2 car garage with super fast Tesla 240V charger + free street parking all around the homebrbrSleeping:br*2 King Bedroomsbr*1 Queen Bedroombr*Queen Bunk Bedroombr(A Pack'n'Play crib can be provided if requested.)brbrAll bathrooms are fully-stocked with fluffy towels, washcloths, & designer Ouai body wash, shampoo, conditioner products.brbrUkrainian Village is a quiet and family friendly neighborhood that's extremely convenient for accessing all of Chicago's main attractions:brbr-Grant Park (Lollapalooza, NASCAR, etc): 11 minutesbr-McCormick Place (Convention Center): 13 minutesbr-Randolph Street (Hottest Restaurants/Bars): 6 minutes`br-Magnificent Mile (Premier Shopping District): 12 minutesbr-Downtown Chicago (Theaters/Restaurants/Shopping): 14 minutesbr-Lincoln Park Zoo: 13 minutesbr-United Center (Bulls/Concerts/2024 DNC): 3 minutesbr-Wrigley Field (Cubs/Concerts): 20 minutesbr-Soldier Field (Bears/Concerts): 13 minutesbr-Guaranteed Rate (White Sox): 12 minutesbrbrTransportation:br-O'hare Airport: 21 minutesbr-Midway Airport: 25 minutesbr-Union Station: 11 minutesbr-Ogilvie Train Station: 9 minutes
Bed 4

Bed

Bath 3

Bath

Sleep 10

Sleeps

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Exceptional(3)

$329.86

/ Nightly
Hotel

Relax in 2 Family-Friendly Suites w/ Heated Pool & Hot Breakfast Near Airport

Chicago, Illinois, United States

Our accommodations offer comfort and convenience with separate living areas and in-room amenities like a mini-fridge, microwave, and coffee maker. Enjoy a complimentary hot breakfast, then explore nearby Rosemont Theater or Rivers Casino. With easy access to downtown Chicago and a short walk to the Cumberland CTA Station, your stay is relaxing and well connected.brbrThis listing is for 2 separate rooms within a hotel. The price shown in the listing covers all 2 rooms.brbr✦ Each room is 375 sq. ft, equipped with complimentary toiletries, standard quality 43-inch TV, available with Premium cable.brbr✦ Rooms are not adjoining and possibly not next to each other. Spaces are assigned upon arrival based on availability.brbr✦ Cleaning services included in the nightly price.brbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 21 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 04:00 pm.brbr✦ You may keep your luggage at the front desk if you arrive early.brbr✦ Public or shared fitness center open 24/7, available in the property.brbr✦ Indoor shared pool available all year, opened from 9:00AM to 9:00PM.brAdditional features:br • Heated poolbrbr✦ Paid parking lot – 1 space(s), available for $32 per day.brbr✦ Shuttle service is available upon reservation between 5:00AM and 11:00PM.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $200 per night refundable deposit, returned after check-out if no damages occur.brbr✦ Pets are welcome with an additional charge of $50.00 (per pet per night). 2 Cats/Dogs per unit | Up to 50 lbs eachbrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ Early check-in is subject to availability for a fee.brbr✦ Free buffet breakfast available daily 7:00 AM to 10:00 AMbrbr✦ Pets cannot be left unattendedbrbr✦The required refundable security deposit is charged per night on a valid credit card.
Bed 4

Bed

Bath 2

Bath

Sleep 8

Sleeps

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$329.86

/ Nightly
Hotel

Experience Quiet Comfort in 2 Family-Friendly Suites w/ Pool & Free Parking

Chicago, Illinois, United States

Our accommodations offer comfort and convenience with separate living areas and in-room amenities like a mini-fridge, microwave, and coffee maker. Enjoy a complimentary hot breakfast, then explore nearby Rosemont Theater or Rivers Casino. With easy access to downtown Chicago and a short walk to the Cumberland CTA Station, your stay is relaxing and well connected.brbrThis listing is for 2 separate rooms within a hotel. The price shown in the listing covers all 2 rooms.brbr✦ Each room is 375 sq. ft, equipped with complimentary toiletries, standard quality 43-inch TV, available with Premium cable.brbr✦ Rooms are not adjoining and possibly not next to each other. Spaces are assigned upon arrival based on availability.brbr✦ Cleaning services included in the nightly price.brbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 21 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 04:00 pm.brbr✦ You may keep your luggage at the front desk if you arrive early.brbr✦ Public or shared fitness center open 24/7, available in the property.brbr✦ Indoor shared pool available all year, opened from 9:00AM to 9:00PM.brAdditional features:br • Heated poolbrbr✦ Paid parking lot – 1 space(s), available for $32 per day.brbr✦ Shuttle service is available upon reservation between 5:00AM and 11:00PM.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $200 per night refundable deposit, returned after check-out if no damages occur.brbr✦ Pets are welcome with an additional charge of $50.00 (per pet per night). 2 Cats/Dogs per unit | Up to 50 lbs eachbrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ Early check-in is subject to availability for a fee.brbr✦ Free buffet breakfast available daily 7:00 AM to 10:00 AMbrbr✦ Pets cannot be left unattendedbrbr✦The required refundable security deposit is charged per night on a valid credit card.
Bed 4

Bed

Bath 2

Bath

Sleep 8

Sleeps

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$164.43

/ Nightly
Hotel

Enjoy A Clean & Quiet Suite w/ Kitchenette & Pool | Minutes from O'Hare Airport

Chicago, Illinois, United States

Our accommodations offer comfort and convenience with separate living areas and in-room amenities like a mini-fridge, microwave, and coffee maker. Enjoy a complimentary hot breakfast, then explore nearby Rosemont Theater or Rivers Casino. With easy access to downtown Chicago and a short walk to the Cumberland CTA Station, your stay is relaxing and well connected.brbrThis listing is for a room within a hotel.brbr✦ Your room is 375 sq. ft, equipped with complimentary toiletries, standard quality 43-inch TV, available with Premium cable.brbr✦ Cleaning services included in the nightly price.brbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 21 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 04:00 pm.brbr✦ You may keep your luggage at the front desk if you arrive early.brbr✦ Public or shared fitness center open 24/7, available in the property.brbr✦ Indoor shared pool available all year, opened from 9:00AM to 9:00PM.brAdditional features:br • Heated poolbrbr✦ Paid parking lot – 1 space(s), available for $32 per day.brbr✦ Shuttle service is available upon reservation between 5:00AM and 11:00PM.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $100 per night refundable deposit, returned after check-out if no damages occur.brbr✦ Pets are welcome with an additional charge of $50.00 (per pet per night). 2 Cats/Dogs per unit | Up to 50 lbs eachbrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ Early check-in is subject to availability for a fee.brbr✦ Free buffet breakfast available daily 7:00 AM to 10:00 AMbrbr✦ Pets cannot be left unattendedbrbr✦The required refundable security deposit is charged per night on a valid credit card.
Bed 2

Bed

Bath 1

Bath

Sleep 4

Sleeps

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$1016.74

/ Nightly
Private Vacation Home

Elegant 4 br Old Town Home; Private Yard; Parking; Amazing Location

Chicago, Illinois, United States

Most incredibly located, sun-filled home with designer kitchen, marble baths, and open-concept living areas—perfect for weekend friend getaways and weekday family or work trips.brWalkable to so much of what Chicago has to offer, this spacious townhouse is located on a quiet, safe neighborhood street in historic Old Town.br4 bedrooms, 4 baths, 2 outdoor spaces, fully stocked kitchen, 1-car parking, and laundry. Pets are welcome! What else could you possibly need brbrPlease turn to the photos to get enchanted by this stunning space and to see the floor plan with layout and sleeping arrangements.brbr** SPECIAL FEATURES ** br• Open-plan living/dining area with a fireplacebr• Soaring ceiling br• Private enclosed front yard and a balconybr• Full kitchen on the first floor plus kitchenette and bar on the top floorbrbr**OTHER AMENITIES**br✦ washers and dryerbr✦ free Wi-Fi throughout the propertybr✦ free luggage storage in the garage, as well as extended free parking before check in time and after checkout may be available.br✦ free EV chargerbrbr**EXTRAS**br• late check out at 1 pm- $125br• early check in at 1 pm- $125br• worry free cleaning package- $125. Please read the details at the bottom.brIMPORTANT: I am unable to charge your account for the additional services. Please contact me in advance to arrange payment through Vrbo. brbr**BEDS**br- 7 queensbr- 1 double futon, 1 queen floor mattresses, 1 couch and a crib brbr**SMALL PRINT**br✦ The brown line train is nearby and you can hear it in some parts of the house. You can also sometimes here the guests in the townhouse next door.br✦ There is another rental on the property. The two share a wall but do not share any spaces inside and have separate entrances. brbr**ACCESSIBILITY**brThere are 14 steps from the main floor to second floor bedroomsbrbr**WORRY FREE CLEANING PACKAGE**brAt check out, you will need to take care of trash overflow, dishes, exuberant messes, and any food you brought. The worry free package covers any and all cleaning. Just walk out in the morning (you do need to move furniture back if you make any changes to layout). Note that this fee is additional to my regular cleaning fee you pay when you book the place. This package is best for those who want to decorate, cook a lot, are traveling as a group and would rather split the extra fee than worry about anything in the morning.brbr**HOUSE RULES**brThe presence of more than 18 guests is unlawful. A guest is anyone at the property, staying the night, or just visiting. Minors need to have a responsible adult present. Unredacted ID will need to be provided for primary booker prior to your arrival for advance reservations and for everyone spending any time at the property for reservations made less than 30 days in advance. There is a counter installed. I utilize a private security firm. If the counter shows more than the registered number of people or if I get a noise complaint from neighbors, security will be immediately dispatched. brbr**DECORATING THE HOUSE**brYou are welcome to decorate the house. If you attach anything to the walls, please use paint-safe tape and remove it prior to your departure. There is a $200 glitter and confetti fee.brbrABOUT THE NEIGHBORHOOD:brThe house is in east Old Town- best neighborhood in Chicago for both families or if you are looking to have fun. While the street itself is very quiet, tree lined and barely has cars passing by, as soon as you turn the corner, you are in the center of everything! Wells street restaurants and bars are steps away. Lincoln Park with the zoo, farm, pond, open spaces and farmers market is a 7-10 min. walk. North avenue beach is the same distance. It is perfect for walks, picnics, boat rides or good old fun in the sand. The beaches are free to the public and have breathtaking city views. Grocery shopping is made easy, seeing as Plum Market and Jewel are located right in the neighborhood. Nearby coffee shops include a 24 hour Starbucks and La Fournette. There are 103 restaurants within a 15 minute walk including some of Chicago's top restaurants including Kamehachi, Topo Gigio, The Fireplace Inn, and Woodies Flat. Bars and lounges are abundant on Wells and are all 1-2 minute walk. Shopping in Old Town is a unique experience; the majority of shops in this neighborhood are boutiques rather than well-known chain stores. Therefore, each and every store is cozy, intimate and filled with one-of-a-kind goods. The Lincoln Park Zoo is a world of wildlife in the shadow of skyscrapers. The Second City only two blocks away and it is a famous theater that specializes in sketch comedy and improv, and has been delighting audiences for over 50 years. Oak street and beginning of Michigan avenue is about 15-20 minute walk.brbrGETTING AROUND:brThe house is a five minute walk from the Brown Line and the Purple Line at the Sedgwick stop and an eight minute walk from Red line at Clark. It takes be about 15 min to walk to Michigan Ave and Wells street bars are a minute away. Buses and cabs are also easily accessible. It is about a 3 minute drive to get onto Lake Shore drive at LaSalle and about 8 minutes to Kennedy expressway at North Avenue.brbrWILDLIFE:brYou will encounter wildlife while staying at the property. Here is what you can expect most commonly:brSpiders and ants are common in Chicago. They get as high as 95th floor of John Hancock building. While we do our best to combat them, it is nearly impossible during high season.brBees, wasps, yellow jackets are abundant throughout the city. While we take care of any nests on the property, I cannot control them in the air and beyond my boundaries.brbrThe house is best for bachelor, bachelorette and friend groups as well as business travelers. It is not child proof.
Bed 4

Bed

Bath 4

Bath

Sleep 18

Sleeps

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Exceptional(1)

$329.86

/ Nightly
Hotel

2 Comfortable Suites Perfect for Families & Groups

Chicago, Illinois, United States

Our accommodations offer comfort and convenience with separate living areas and in-room amenities like a mini-fridge, microwave, and coffee maker. Enjoy a complimentary hot breakfast, then explore nearby Rosemont Theater or Rivers Casino. With easy access to downtown Chicago and a short walk to the Cumberland CTA Station, your stay is relaxing and well connected.brbrThis listing is for 2 separate rooms within a hotel. The price shown in the listing covers all 2 rooms.brbr✦ Each room is 375 sq. ft, equipped with complimentary toiletries, standard quality 43-inch TV, available with Premium cable.brbr✦ Rooms are not adjoining and possibly not next to each other. Spaces are assigned upon arrival based on availability.brbr✦ Cleaning services included in the nightly price.brbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 21 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 04:00 pm.brbr✦ You may keep your luggage at the front desk if you arrive early.brbr✦ Public or shared fitness center open 24/7, available in the property.brbr✦ Indoor shared pool available all year, opened from 9:00AM to 9:00PM.brAdditional features:br • Heated poolbrbr✦ Paid parking lot – 1 space(s), available for $32 per day.brbr✦ Shuttle service is available upon reservation between 5:00AM and 11:00PM.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $200 per night refundable deposit, returned after check-out if no damages occur.brbr✦ Pets are welcome with an additional charge of $50.00 (per pet per night). 2 Cats/Dogs per unit | Up to 50 lbs eachbrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ Early check-in is subject to availability for a fee.brbr✦ Free buffet breakfast available daily 7:00 AM to 10:00 AMbrbr✦ Pets cannot be left unattendedbrbr✦The required refundable security deposit is charged per night on a valid credit card.
Bed 4

Bed

Bath 2

Bath

Sleep 12

Sleeps

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Exceptional(1)

$164.43

/ Nightly
Hotel

O'Hare Suite Perfect for Families w/ Free Breakfast & Onsite Heated Pool

Chicago, Illinois, United States

Our accommodations offer comfort and convenience with separate living areas and in-room amenities like a mini-fridge, microwave, and coffee maker. Enjoy a complimentary hot breakfast, then explore nearby Rosemont Theater or Rivers Casino. With easy access to downtown Chicago and a short walk to the Cumberland CTA Station, your stay is relaxing and well connected.brbrThis listing is for a room within a hotel.brbr✦ Your room is 375 sq. ft, equipped with complimentary toiletries, standard quality 43-inch TV, available with Premium cable.brbr✦ Cleaning services included in the nightly price.brbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 21 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 04:00 pm.brbr✦ You may keep your luggage at the front desk if you arrive early.brbr✦ Public or shared fitness center open 24/7, available in the property.brbr✦ Indoor shared pool available all year, opened from 9:00AM to 9:00PM.brAdditional features:br • Heated poolbrbr✦ Paid parking lot – 1 space(s), available for $32 per day.brbr✦ Shuttle service is available upon reservation between 5:00AM and 11:00PM.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $100 per night refundable deposit, returned after check-out if no damages occur.brbr✦ Pets are welcome with an additional charge of $50.00 (per pet per night). 2 Cats/Dogs per unit | Up to 50 lbs eachbrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ Early check-in is subject to availability for a fee.brbr✦ Free buffet breakfast available daily 7:00 AM to 10:00 AMbrbr✦ Pets cannot be left unattendedbrbr✦The required refundable security deposit is charged per night on a valid credit card.
Bed 2

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Bath 1

Bath

Sleep 6

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Exceptional(23)

$639.59

/ Nightly
Private Vacation Home

Mayors Manor, Zen Garden Oasis, Hot Tub & Sauna in Central Chicago, 8-12 guests

Chicago, Illinois, United States

Welcome to MAYORS MANOR, with a 24/7 dedicated team ensuring a comfortable and unforgettable stay.brbr✔ Spacious & Stylishbr✔ Sleeps 8-12 Guests (8 adults + 4 kids)br✔ 2 car garage parkingbr✔ Baby / Toddler FriendlybrbrA+ LOCATIONbr✔ Vibrant Neighborhoodbr✔ Amazing Bars & Restaurantsbr✔ Fun Coffee Shops & Bookstoresbr✔ 5 min run to a beautiful parkbrbrFAMILY FUNbr✔ Kitchen & 8-Seat Diningbr✔ Movie Theatre w/ Foosball, Board Gamesbr✔ Comfortable Beds + extra linensbr✔ Outdoor Deck with Grillbr✔ Backyard Patio with Hot Tub & SaunabrbrSTEP BACK INTO CHICAGO'S HISTORYbrbrThis is the one vacation spot that will make you feel like you are in Chicago! brbrWith photos of Chicago's skyline to its most famous mobster and the prohibition era, the space is simply beautiful. brbrLIVING ROOMbr- walk into the living room with a projector and a dedicated workspace (desk and comfortable chair). brbrKITCHENbr- the bright, fully stocked kitchen can seat up to 8 people at a time. br- has everything you can think of to cook the perfect family meal: pots, pans, toaster, kitchen cutlery, coffee maker, bowls, kid-friendly cups & silverware, you name it. brbrQUEEN SUITE 1brThe upper level bedroom has a comfortable queen bed, and is stocked with interesting books. brbrJUNIOR SUITEbrThe 2nd upper level bedroom has 3 single beds (bunk beds and a trundle), and is stocked with children's books and toys.brbrOUTDOOR DECKbrDown the hall, open the door to access a large and spacious deck, standing over a beautiful large patio -- perfect for gatherings and some outdoor quality time. brbrLAUNDRY brDownstairs, you will have full access to a private laundry room. brbrBAR AREAbrOn the other side of the French doors, you will see a beautiful bar & TV -- wind down, catch all the games over some drinks, or enjoy hosting large groups. brbrBATHROOM 2brBoth of the upper & lower bathrooms have spa lights, mirrors, and elegant lighting. brbrQUEEN SUITE 2brDown the hall, there will be another bedroom, with a queen sized bed and closet space. brbrMOVIE ROOMbrFurther down the hall is the Movie Room -- 3 futons, 2 small beds -- with a movie projector and a Foosball table. This room can comfortably sleep 2 adults or 5 kids. brbrBACKYARDbrWalk out into this garden oasis with a beautiful patio setup to enjoy the outdoors. Soak in the sun, drink some coolers, and hang out in the hot tub with your company. Break into a sweat, and try out our new sauna (follow instructions for adding water & heating!). brbrWe hope you love this space we uniquely designed for your enjoyment.brbrNOTES:br1. Hot tub does not heat when below 45 degrees Fahrenheit. br2. Propane tank for BBQ Grill available upon request.brbrWe are wholeheartedly committed to ensuring you have a wonderful experience staying at Mayor's Manor. With a 24/7 concierge, and the latest technology, we are able to provide almost anything on demand!brbrWe also offer same-day cleaning for longer-term stays. brbrOur ground rules:br1. No parties or large gatheringsbr2. Quiet hours are 10 pm - 7 am (11 pm on weekends)br3. Guests outside the reservation must leave before quiet hours. br4. No smoking indoors (vapes ok)br5. No glitter, or use of anything difficult to clean.brbrVEHICLE RENTALbrWe have a sporty 7-passenger SUV that can be booked with your stay, based on availability. Please inquire if you are interested in pairing this discounted service with your stay.brbrPOINTS OF INTEREST brDowntown, Chicago: 3.6 milesbrMcCormick Place: 2.4 milesbrUnited Center: 3.9 milesbrSoldier Field: 3.6 milesbrWintrust Arena: 2.3 milesbrSox Stadium: 1.7 milesbrWrigley Field: 9.1 milesbrIIT Campus: 2.1 milesbrUni. of Chicago Campus: 6 milesbrUIC Campus: 2.6 milesbrChinatown: 1.6 milesbrRadius (Venue): 1.4 milesbrOakwood Beach: 3.8 milesbr31st Street Beach: 2.7 milesbrMidway Airport: 7.4 milesbrO'Hare Airport: 18.8 miles
Bed 4

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Bath 2

Bath

Sleep 12

Sleeps

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