Vacation Home Rentals By Owner In Chicago, IL

$988.36

Chicago Bootlegger House Sleeps 11-22 with 3 parking spots

Chicago, Illinois, United States

This is a single family home that was originally built and owned by a bootlegger during the prohibition period of the 1920's. He had a boat in nearby Belmont Harbor and would sail to Windsor Canada to pickup whiskey and then sell it from the backyard to locals. He was always on the lookout for cops. There is one remaining escape door in one of the bedrooms on the main level. We keep it locked, but it still works to get you outside fast.brbrLarge enough to sleep 22 people with plenty of space to mix, mingle and play (including a foosball table). 2 car garage and outside pad for large vehicles. Awesome location in East Lakeview near Wrigley, Lincoln Park and more.

6

Bed

2

Bath

20

Sleeps

$154.66

/ Nightly

Private Vacation Home

Charming 1BR townhome in fantastic Wicker Park, Attached Garage and EV Charger

Chicago, Illinois, United States

Enjoy a stylish experience at this centrally-located Townhouse with attached garage AND an EV Charger! Outstanding Wicker Park location, 1 block from entrance to the famous '606 Trail', numerous coffee shops, restaurants, clubs and bars! Approximately 1000 sq. ft. of living space on 3 floors, washer/dryer and outdoor space! Walking distance to 2 Blue Line stops (Damen & Western) as well as the 50 & 49 buses (also Damen and Western). 1 month minimum term!

Bed

Bath

Sleeps

$979.0

/ Nightly

Private Vacation Home

Spacious / New - 8BD/4BTH - Sleeps 16 + Garage!

Chicago, Illinois, United States

NEW HOME/NEWLY FURNISHED! This 8 bed home is ready to host! My space accomodates 18 guests with 10 beds and 4 full baths and a fully stocked kitchen. We are minutes from the best restaurants and bars. Both MDW and ORD airports are only 20-30 min from the home. The space also offers spacious gathering rooms, bedrooms, and a laundry room on the bottom level plus a 1 car garage, driveway, and free street parking!brbrMy place is great for multiple families, business travelers, large groups, or couples! This single family home is situated on a residential street with planty of free street parking for your convenience. With comfortable and stylish furnishings we want you to feel this is your home away from home!brbrThe space:brbrTop Floor:br1st bedroom - 1 queen bedbr2nd bedroom - 2 queen beds (note bedroom 1 and 2 are adjoining rooms)br3rd bedroom - 1 queen bed br2 full bathroomsbrbrMain Floor:br1st bedroom - 1 queen bedbr2nd bedroom - 1 queen bedbr3rd bedroom - Bunk bed with full bed and twin bedbr1 full bathroombrbrBottom Floor:br1st bedroom - 1 queen bedbr2nd bedroom - 1 queen bedbr1 full bathroombrbrbrIn addition I provide the following amenities to all my guests!br- My cleaners are professionally trained and follow a tightly regimented cleaning and sanitizing checklist.brThey are equipped with a full complement of professional cleaning tools and chemicals including abrhospital-grade disinfectant.br- Fresh towels and linensbr- Wireless internet is always availablebr- TV with streaming optionsbr- Kitchen appliances including a microwave, coffee pot with a reusable filter,brtea kettle, and toasterbr- Keurig and coffee makerbr- My place is FULLY STOCKED with all the amenities of home like shampoo,brconditioner, body wash, paper towels, toilet paper, tissue, sponges, handbrsoap and dish soap.br-The full sized kitchen is stocked with cookware, utensils, glasses, cutlery, sharp knives, cutting boards,brbaking sheets and all the basic tools like wine openers, cheese graters, vegetable peelers, pizza cutters, etc.br- Hair dryerbr- Luggage racks and hangersbrbrCheck-in is effortless and 100% contact-free. Your private access code works on all exterior door keypads, allowing you to arrive and settle in on your own schedule. We’ve designed the process to be completely autonomous, though our team is always just a message away if you need us!brbr*This home is professionally curated by Hosty Co, Chicago’s premier boutique management team. We specialize in high-touch service, 5-star aesthetics, and seamless stays.*brbr**Follow the journey: Find us on social @hosty_co_chibnb for a look at our full portfolio and `insider only` Chicago neighborhood guides.**brbrTo protect the quality of our home and the harmony of our neighborhood, we specifically host:br*Corporate Travelers seeking a refined, reliable home base.br*Families visiting for holidays or major Chicago milestones.br*Urban Explorers who value a quiet, high-end retreat.brbrBooking Requirements: We operate under a strict `Good Neighbor` policy. To ensure we are the right fit for your trip:br*Tell Us Your Story: When inquiring, please include a brief note about your trip and your group. We love knowing how to best prep the space for your arrival!br*Vetting: We prioritize guests with 100% ID verification and a track record of positive reviews.br*Zero Tolerance: To maintain our home`s integrity, parties and unauthorized gatherings are strictly prohibited.brNo shoes in the housebrNo smoking of any kind indoorsbrNo guests outside of the group in the home at any pointbrNo events

4

Bath

16

Sleeps

$1399.0

/ Nightly

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

4

Bed

3

Bath

17

Sleeps

$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

Bath

Sleeps

$135.79

/ Nightly

Private Vacation Home

King Comfort apartment, Quiet, Clean, AC & WiFi

Chicago, Illinois, United States

brEnjoy a private and peaceful stay in our fully equipped basement apartment—perfect for travelers seeking comfort, privacy, and convenience.brbrThis cozy space features a King-size bed, a foldable Twin bed, and a Smart TV for your entertainment. Stay cool with AC, connected with fast WiFi, and cook your favorite meals in a full kitchen equipped with essentials.brYou’ll have easy self check-in, plus free street parking passes, making your arrival smooth and stress-free.brLocated in a quiet Chicago neighborhood with quick access to restaurants, parks, shops, and local attractions, this apartment is ideal for both business travelers and families.brbrKick back, relax, and enjoy your home away from home.

Bed

Bath

Sleeps

$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

4

Bed

3

Bath

10

Sleeps

$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

Bath

Sleeps

$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

4

Bed

2

Bath

12

Sleeps

$334.77

/ Nightly

Private Vacation Home

Super Paradise Chicago

Chicago, Illinois, United States

Modern and luxurious, open plan,brLARGE full equipped back yard also included, located near Midway Airport and 12 minutes to downtown Chicago.brbrTwo cozy and relaxing BedroomsbrbrLarge living room, cinemabr3 Smart TVbrDolby Surround Sound systembrbrFull Equip Stainless Steel kitchenbrStovebrOvenbrDish washerbrRefrigeratorbrbrFull 1.5 SPA bathroombrWhirlpool jetted massage JacuzzibrStanding Shower/glass doorbrThe spacebrThis place its Modern Elegant Spacious with attention to detail and luxurybrLuxury bathroom with Standing shower or Whirlpool with massage jets.brHigh fidelity entertainment CenterbrMultiple HD TVbrFull equipped Stainless KitchenbrBeautiful zen garden in the back of the house with places to relax cook and eatbrGuest accessbr*The entire place its private for your use and enjoyment. with your private entrance and electric key code entrybrOther things to notebrAfter the first 2 guest, each additional guess will be charged $ 60 per night.brbrBy having your private access at the house you can come and go at any time day or night.brRegistration DetailsbrR17000014665

Bed

Bath

Sleeps

$404.0

/ Nightly

Private Vacation Home

1 #31 - 4 Bedroom Condo - McCormick Place, Wintrust Arena, Chinatown

Chicago, Illinois, United States

Beautiful and newly furnished condo in the heart of Chicago Chinatown area with 4 bedrooms, 2 baths, two separate living room two upscale kitchens so your guests could spread out. This premium property has proximity and amenities that caters to business travelers and tourists alike. The property has 11 beds that can accommodate 16+ guests. Minutes to Downtown, McCormick Place, and popular attractions. Walking distance to public transit, stores, Walgreens, Starbucks, and many great restaurants.brbr• In-building washer and dryerbr• Central air & heat, smart thermostatbr• 4 bedrooms / 2 Full bathroomsbr• Sleeps 14+ guestsbr• 8 Beds (1 Bunk, 4 Double, 1 Single, 2 Sofa beds)br• Super comfortable, premium memory foam mattresses and beddingbr• Additional portable memory foam mattresses available for extra chargebr• Fully equipped and stocked kitchensbr• Keurig coffee maker with pods, hot water kettle, microwave and morebr• Linen, premium shampoo, body wash, and towels providedbr• Iron, ironing board, & hairdryer providedbr• Business and laptop friendly workspaces in every bedroombr• High speed internet / wifibr• 55-inch flat-screen Roku TVs with Chromecast & Airplay

4

Bed

2

Bath

14

Sleeps

$164.8

/ Nightly

Private Vacation Home

Commuter-Friendly Bungalow in Chicago's South Side

Chicago, Illinois, United States

1 Mi to Advocate Trinity & South Shore Hospitals | Work-Focused StaysbrbrThis inviting South Side vacation rental is a smart choice for medical professionals, faculty, and business travelers seeking a dependable base. Set in the historic Pill Hill area, the Chicago home balances quick city access with a calm, residential feel. In your downtime, stroll nearby green spaces, catch lake breezes along the shoreline, or explore Hyde Park’s cafés — then return to a space that truly feels like home!brbr-- THE PROPERTY --brbrSLEEPING ARRANGEMENTSbr- Bedroom 1: 1 queen bedbr- Bedroom 2: 2 full bedsbr- Bedroom 3: 2 full bedsbrbrINDOOR LIVINGbr- Large reclining sectionalbr- Electric fireplacebr- Smart TVsbr- Dining tablebrbrSHARED OUTDOOR LIVINGbr- Small fenced backyardbr- Patio w/ grill & dining setbrbrKITCHEN br- Stove/oven, refrigerator, microwavebr- Toaster, blenderbr- Drip coffee maker (bring your own coffee)br- Cooking basics, spicesbr- Dishware/flatwarebr- Trash bags & paper towelsbrbrGENERAL br- Free WiFibr- Shared washer/dryer (detergent provided)br- Central A/C & heating, ceiling fansbr- Linens/towels, complimentary toiletriesbr- Iron/boardbr- Keyless entrybrbrFAQbr- 2 exterior security cameras (facing out)br- Quiet hours (8:00 PM-8:00 AM)br- Homeowner lives on-site occasionally (downstairs unit)brbrACCESSIBILITYbr- Single-story home w/ basementbr- 5 steps to enterbr- All bedrooms & 1 full bathroom on main levelbrbrPARKINGbr- Street parking (2 vehicles; first-come, first-served)brbr-- THE LOCATION --brbr- Quiet residential street w/ easy access to I-90br- 3 miles to Rainbow Beach Parkbr- 4 miles to Jackson Parkbr- 7 miles to UChicago Medicinebr- 10-14 miles to Rate Field, Soldier Field & United Centerbr- 16 miles to Navy Pierbr- 19 miles to Chicago Midway Int'l Airport & 30 miles to Chicago O'Hare Int'l Airportbrbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you’ll never want to leave. You can relax knowing that our properties will always be ready for you and that we’ll answer the phone 24/7. Even better, if anything is off about your stay, we’ll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smokingbr- No pets allowedbr- No events, parties, or large gatheringsbr- Please observe quiet hours from 8:00 PM to 8:00 AMbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbrbrADDITIONAL INFORMATIONbr- This single-story home with a basement requires 5 steps to enter; all bedrooms and 1 full bathroom are located on the main levelbr- The homeowner lives on-site occasionally in the downstairs unit with access to the laundry room and backyard; they may be present during your staybr- Your safety matters. This property features 2 exterior security cameras: 1 camera is on the left side of the house facing the front door, and 1 camera is on the right side of the house facing the back door. The cameras are outward facing and do not look into interior spaces. The cameras record video and sound when activated by motion

Bed

Bath

Sleeps

$201.74

/ Nightly

Private Vacation Home

Located in the Heart of Lincoln Park, walking distance to North Ave beach & more

Chicago, Illinois, United States

Our 3-level townhouse is the perfect space for those relocating, traveling for work, or in town for more extended visits. The private home provides all the comforts of home with 3 bedrooms, 3 1/2 bathrooms, and a sleeper sofa on the lower level. brbrCharacter and charm reside throughout the home with lofted, shipboard ceilings, lavish natural light, hardwood floors, painted brick walls, original built-ins, and meticulously curated decor. Features include a mix of new and vintage furniture, memory foam mattresses, and smart TVs in the living room, family room, and in every bedroom. The home has a smart thermostat system, Nest Smoke & CO detectors, and newer appliances. It's stocked with utensils, glassware, serving-ware, and cookware. brbrThe space is optimal for anyone who wants to enjoy the vibes of this special Chicago neighborhood, including couples, families, friends, or those needing a quiet place to work with the comforts of home. brbrMore about the sleeping spaces:brbrKing bedroom (primary suite on 2nd level):brbr• King-size Article bed with a Layla memory foam mattressbr• Attached bathroom with a bathtub and showerbr• Great for 1-2 peoplebr• Space for an air mattress or pack-n-play if neededbr• Storage with a large closet and built-insbr• A comfy West Elm boucle swivel chairbr• Wall-mounted Roku TVbr• Lovely natural lightbr• Overlooks the courtyardbr• Room does not share a wall with any other bedroombrbrQueen Bedroom (on 2nd level): brbr• Queen-sized Article bed and Layla memory foam mattressbr• Accommodates 1-2 peoplebr• Natural lightbr• TV with Rokubr• No traditional closet but there is built-in storage and hanging spacebr• Room shares a full bathroom (tub and shower) in the hallway with the twin bunk bedroombr• Windows with black out curtains with view of the lovely residential streetbrbrTwin Bunk Bedroom (on 2nd level): brbr• Modern twin-sized bunk beds (weight capacity 250 lbs per bed) each with Layla memory foam mattressesbr• Accommodates 1-2 peoplebr• Natural lightbr• Roku TVbr• Mirrored sliding door closetbr• Built-in storage (books and toys available)br• Room shares a full bathroom (tub and shower) in the hallway with the queen bedroombr• Window with view of the lovely residential streetbrbrQueen Sleeper Sofa (on lower level): brbr• The sleeper sofa is in the family room, but this space can be converted to a semi-private areabr• West Elm sleeper sofa folds out into the living space br• Extra pillows and blankets are providedbr• Wall-mounted TV with Rokubr• Original built-in shelvingbr• Bathroom with a shower is down the hallbr• Space includes desk area, laundry room, and additional storage spacebrbrMore on the rest of the home: brbrWhen you enter the home, you're greeted with spectacular natural lighting that fills the space. The open floor plan connects the living room, dining room, and kitchen. brbrThe living room has a 50 wall-mounted smart tv with Roku that sits above the fireplace, a leather sectional by Article, and a woven cave chair. The room leads out via sliding glass doors to the private patio.brbrThe dining room has a vintage tulip table, seating for 4-6 people with modern Article chairs, a Bluetooth speaker with radio and CD player, and original built-ins filled with arts / craft supplies and games / activities.brbrThe kitchen features endless built-in storage, modern appliances, a stocked upon arrival Nespresso machine, an electric kettle, cookware, utensils, dishes and glassware.brbrAs you walk up the stairs to the second level, you'll find an extra-large skylight—the source of the homes amazing natural light.brbrUpstairs, you'll find three bedrooms and two full bathrooms.brbrDownstairs on the lower level, past the family room and separated by a door is the laundry room with a washer and dryer, full bathroom, and extra storage space. brbrThe home's two outdoor areas include a private patio in the front with lovely brick walls and Floyd dining furniture. The back of the home has a shared, landscaped courtyard that leads to the gated garbage/recycling area. All outdoor spaces are private to residents and gated.

Bed

Bath

Sleeps

$385.23

/ Nightly

Private Vacation Home

Chicago Riverhouse with private fenced in oasis

Chicago, Illinois, United States

Close to must see Chicago restaurants and nightlife, yet nestled in nature! brThis 1937 Print Shop is seated between the Chicago River & Forest Preserves, with trails & river walks, 3 miles to the beach, near Lake Shore Drive & 90/94, nearby Lincoln Square , Andersonville, and seasonal waterfalls, brunch nearby. This 2-bed, 2-bath home one level. 5star Chef`s kitchenbr9’ x 15’ HD projector, comfy beds, double shower head shower room, near nature. Relax on our private patio and illuminating sofabrbr- Gorgeous sun drenched city retreat with 2 bedrooms and 2 bathroomsbr Single-level open concept home with amazing skylights and nature views from withinbr - Front bedroom/bathroom suite with a double shower head in shower room and double sinkbr - Cozy 2nd bedroom with 2 skylights and comfy queen bedbr - Lush sink-in pillows in each bedroombrbrbr - Private outdoor space fenced in with illuminating sofa (available May-Oct) and a dining space for 6-8br-Hammock for two with mosquito netbr-Propane or Charcoal grill. Propane provided. Charcoal not provided. brbr -Pet friendly (pets must be left in crate when owners not present on the property) PLEASE NOTE a you must select pet fee if you’re bringing a pet. brbr - Access to nearby public transportation or Uber/Lyftbr - Free street parkingbr - High-definition projector br - Stream your favorite apps via ROKU setupbr - free high speed internet WiFi. Great for remote workersbrbrbrSecurity cameras are monitored with recording and audio are located front & back exteriors for your safety. brbr•Pet friendly and always immaculately clean! brbr•A post cleaning video is taken after each cleaning and stored post stay to ensure our cleaning standards are upheld and document how space was provided to each guest. brbr-Property not made childproof. Please supervise children and make sure they are not left near the mirror. No horseplay indoors. br- No children under 18 left alone on the property. brbrOwners & their team clean home and we don’t sleep well if you don’t sleep well! It is our pleasure & pride to offer a quality space and anticipate your traveling needs. If anything arises during your stay we ask you to allow us to rectify. Reach out 24/7 by phone or text for emergencies.brbr- Fully equipped kitchen with complimentary organic coffee, tea, and sugarbrbr - Appliances available:br - Blenderbr - French pressbr - Coffee makerbr - Electric kettlebr - Cookware (pots, pans, soup pot, cookie tray, round baking pan, colander)br - Cutting boardbr - Knivesbr - Dishwasherbr -Air Fryerbr -Microwave located bottom left base cabinet in kitchenbr -Basic spicesbrbr- Outdoor patio for relaxationbrbr- Luxurious shower room with dual headsbrbr- Entertainment on a 20` x 9` HD projector with Chromecastbr - Note: Daytime viewing may appear slightly desaturatedbrbr- Dog-friendly space with a fenced-in yardbrbr- Please avoid the closets in the front bedroom and living room during your staybrbrI’m always available, and happy to help with tips or anything I can do to help make your planning or stay fantastic. Also check out the Host Guide Book I created of local must do’s and great eats & check our reviews to see what our guests love nearbybrbr- Safe Family Area:br - Lots of family-friendly, dining, and night life activities in Host`s Guide in listingbrbr- Convenient Access to Chicago`s Best Attractions:br - 4 blocks from Forest Preserve with trails where deer sightings are the normbr - Walking distance to Riverwalk trails along Chicago River north branchbr -Many gorgeous parks nearby, including Peterson Park with it`s forested paths br and seasonal waterfallsbr - 2.5 miles from Andersonville, home to some of Chicago`s best restaurants and bars- A MUST SEE AREA TO EAT AND SHOP YOUR WAY THROUGH!br - 3.5 miles from Pratt & Hollywood beachesbr -Nearby Whole Foods, Asian Market Joong Boo, Jewel, 7/11 convenient storebr -Nearby Devon St which is Chicago`s Little Indiabr -20 min from King Spa for all day sauna, spa, and massagesbr -15 min from Lincoln Square area for great dining and local shopsbr -20 min from Skokie and the Old Orchard outdoor shopping mall and theatersbrbr- Easy Transportation:br - 1.5 miles from Interstate 90/94br - 30-minute drive from O`Hare International AirportbrbrUber, walk, drive, bus & trains are accessible but there’s a short walk. There’s also great free parking on the street. See zoning notes in main description. Near to exciting Andersonville neighborhood, “Little India” on Devon, Rogers Park, Pratt beach, shops in Lincoln Square, and not too far from other great areas like Lincoln Park, Lakeview, and more.brbrPlease send a quick email with what brings you to Chicago & who you’re traveling with to complete your booking. It helps us to know who you are make your stay great! brbrExterior cameras front & back entrances. brbrNo parties allowed, per Airbb policy. brbrPlease avoid cooking foods that create lingering smells, especially on or near departure datebrbrSmall gatherings & visitors must be approved in advance via the app, and the rental is for a maximum of 4 or less overnight guests. Thank you for understanding. brbrGuests not on the reservation must be cleared in writing via the app, PRIOR to them entering the property. Violation of guest policy will result in the immediate termination of the reservation, so please communicate with us so we can do our best to graciously welcome your guests. This is a party deterrent, but your family is welcome. brbrPet friendly space kept immaculately clean. Pets must be crated if left behind at the house. brbr*****PLEASE NOTE a you must select pet fee if you’re bringing a pet. brbr-Property not made childproof. Please supervise children and make sure they are not left near the mirror. No horseplay indoors. br- No children under 18 left alone on the property. brbrOutdoor furniture available to enjoy May-October. The furniture is wiped down and leaves are blown at each turn over BUT if inclimate weather occurs on your day of arrival or during your stay, the outdoor furniture and patio maybe covered with debris we cannot control. brbrIDs of anyone entering will be asked for to complete booking in parties more than 4, or if you have no previous reviews. Your name on the platform must match your ID. You may not book with a nickname on your platform profile. Your profile must be in English with a name written in English or we will ask for your ID or passport. No reservations will be accepted from guests who have not filled out their profile. brbrCheck out my Host Guide in the listing for places I love and hope you will too! brbrThe University across the street has well lit paths for quick walks. The closest park, is Peterson Park to the west off Bryn Mawr (entrance on Central Park, walk north) Very scenic and great place to take nature pics, once you walk in. Ask me how to find the forest trail and (summer only) waterfalls. The northwest corner of the park has a nature center.brbrWe ask that you allow us the opportunity to address any matter that arises during your booking. In most instances we will address immediately and will send in person help if possible. We accept calls and texts and are here to assist promptly.br* Credit card processing fees are non-refundable even in the case of a full refund.brNo shoes indoors, please.brDon`t touch the mirror or open locked closet doorbrDon`t move furniture.br420 friendly, no smoking indoors (smoking on patio permitted. Violators will be subject to a $500 fine.brHang damp towels and leave the shower door open.brNo parties, two guests per room brClean up after yourself and run the dishwasher before leaving.brEnsure the front door locks and don`t leave doors openbrTurn off sofa and projector when not in use.brTreat this home like your own.brPets stay off furniture, doggie towels are orange & brown and located in hall bath closet, clean up pet waste to avoid $100 fine for waste left behindbrPlease respect checkout time 10am. Our team arrives promptly to turn over. We often have guests arriving the same day as your departure and failure to depart on time can cause us delays that will effect next guest. Violators will be charge a min $500 if you depart late. A 10 min grace period is recognized.brDon`t tamper with security cameras or Roku or projector devices to avoid booking termination, and violators will be subject to a $500 fine.brIDs and rental agreement may be required

2

Bed

2

Bath

4

Sleeps

$279.45

/ Nightly

Private Vacation Home

Andersonville Charming 3 Bedroom/2 Bath House with Family Room plus Yard & Patio

Chicago, Illinois, United States

Located in Andersonville - voted the 2nd best neighborhood in the world in 2021 by Time Out - this fully FURNISHED single family home just received a stylish renovation and is the perfect “home away from home”! The entry way starts off the cozy vintage vibe with charming original floors and woodwork. The kitchen was created for those who love to cook and entertain, so this will be one of the most well stocked kitchens you will ever stay in! The refrigerator has an ice maker and a water supply for filling up your water bottles. The oven also has an air fry feature. And yes, there is even a set of vintage china if you are feeling like serving a special meal. The dining room has a an original built-in hutch, an antique sideboard and round dining table that seats 6 - great for entertaining or playing games with your family or friends. There are 3 large bedrooms upstairs along with a full bathroom and a laundry room. The bedrooms are furnished with a king bed, a California king bed and a queen bed. All bedrooms have dresser storage and closets. The bathroom has a soaking tub. The main floor has a den/office that is perfect for working at home but can also serve as a guest room with a pull out futon. There is also a library hutch that has books you can read, games, puzzles and a selection of cookbooks. The other full bathroom is on the main level and features a custom built walk- in subway tile shower and beautiful marble mosaic tile on the floor. There is a beautiful pantry that is set up as a wine and coffee bar area. At the back of the home, there is a sunny family room with a unique original wood wall that is furnished with a couch, a TV and a small table and chairs so you can enjoy the view of the back yard with your morning coffee. There is zoned central heat and air so you can be comfortable no matter where you are in the house. brbrAll utilities are included and high speed wifi is provided. brbrWe are located only half a block from the Clark Street retail/restaurant strip in the Andersonville. The boutique shops and delicious restaurants offer so much variety right outside your door. This lovely tree lined street has a quintessential Chicago neighborhood feel and you will immediately feel like you are part of the community. Only 1 mile to the lake front beaches, parks, bike trails and walking paths – this is part of what makes Chicago a great place to live! Winnemac Park is 4 blocks away. There are several public transportation options – a 10 minute walk to the red line, the brown line or the Ravenswood Metra station. Only a ½ block to the Clark St. bus (22) and easy access to Lake Shore Drive, which is only a few minutes away by car. brbrWe live next door and we love our special neighborhood! We have created this home to share with you and have added a lot of special touches that are not in your typical rental. You will love staying in this home!brbrMonthly furnished rental - FLEXIBLE DATES BETWEEN NOW AND MAY 31ST AND AFTER OCTOBER 1ST. All utilities are included - central heat/ac, electric, gas, water and high speed internet. Two smart TV's with antennas for local channels. First month's rent + $1000 security deposit + $400 cleaning fee due at lease signing. Application fee $75 per adult non-refundable. Excellent credit and income required.

Bed

Bath

Sleeps

$323.54

/ Nightly

Private Vacation Home

Relaxing hot and beautiful 4 bed, 2 baths in peaceful area

Chicago, Illinois, United States

Amazing, warm, relaxing, quite 4 bedroom and two bathrooms. The master bedroom has a 65” Sony tv, recliners and a king size bed. The second bedroom has a nice table, lamp and a queen sized bed. The third bedroom has a nice table, lamp and queen sized bed. The forth bedroom or den has a queen sized bed and private bathroom. The kitchen has high end appliances, Silestone countertops and glass backsplash. This kitchen is very desirable to cook in. The bathrooms are all new custom tile. Enjoy!

4

Bed

2

Bath

12

Sleeps

$390.0

/ Nightly

Private Vacation Home

Urban Farm Stay w/ Skyline Views + Free Parking

Chicago, Illinois, United States

* Clean, peaceful 3BR/2BA unit in a quiet 3-flat * Approx. 30 stairs to reach this 3rd-floor walk-up * Known for comfort, calm, and exceptional cleanliness * Skyline views + 3 private decks for relaxing or reading * Cozy, low-tech stay w/ Smart TV in living room & fast WiFi * Full kitchen, free street parking, family-friendly * Add-ons: seasonal bouquets, private chef dinners by request Experience a Chicago stay like no other at the Farmstay at Herban. Located on a working urban farm, this peaceful 3-bedroom, 2-bath unit offers a unique blend of relaxation, comfort, and natural beauty—just minutes from downtown and some of the city’s best dining and cultural spots. Tucked in a quiet, centrally located neighborhood, you’ll be close to downtown, Restaurant Row, and hidden neighborhood gems. Inside, enjoy: *12-ft ceilings and abundant natural light A fully equipped chef’s kitchen with modern finishes *Spa-style bathrooms for a relaxing retreat *1,600 sq ft of professionally decorated living space *3 private patios and a seasonal rooftop deck with skyline and farm views This low-tech, high-comfort space is perfect for families, couples, creatives, and anyone seeking rest and reconnection. Guests love the peaceful energy, spacious layout, and exceptional cleanliness. Available for vacation stays or as a filming location, the Farmstay at Herban offers a stay that’s as memorable as it is restorative. You'll have full access to the spacious 1,600 sq ft unit, including: Three private patios—perfect for relaxing, reading, or enjoying your morning coffee A bright, peaceful living space with modern comforts The unit is located on the third floor of a walk-up building (approx. 30 stairs). There is no elevator, so please plan accordingly. Want to enjoy more outdoor space Our courtyard is available upon request—just let us know! We respect your privacy but are always nearby if you need anything! Whether it’s a quick question, fresh flowers, or a curated recommendation, we’re happy to help make your stay feel personal and relaxed. We are very close to public transit. The CTA blue and green L stations and and block away from the Jackson bus. If you are unfamiliar with Chicago, we recommend getting around by car. We provide a detailed orientation guide to the house and a list of recommendations of things to see & do during your stay.

Bed

Bath

Sleeps

$819.51

/ Nightly

Private Vacation Home

Chic 4-Bedroom Haven in Ukrainian Village

Chicago, Illinois, United States

Summary:brbrWelcome to our Chic 4-Bedroom Haven in Ukrainian Village, Chicago! brbr- Meticulously curated interior with modern aesthetics brbr- Cozy atmosphere perfect for families or groups brbr- Fully equipped kitchen with top-notch appliances brbr- Four uniquely charming bedrooms with luxurious linens brbr- Thoughtful design choices throughout brbrBook your stay with TheDreamRentals today!brbrbrbrThe Space:brbrWelcome to our Chic 4-Bedroom Haven in the heart of Ukrainian Village, Chicago! This meticulously curated home is a true interior designer's dream come to life, offering a perfect blend of style, comfort, and convenience for your stay. brbrbrbrComfortable Accommodation: brbr- Four uniquely charming bedrooms brbr- Comfortable beds with luxurious linens brbr- Ample storage and natural light brbrbrbrInterior Feeling: brbr- Thoughtful design choices throughout brbr- Carefully selected color palettes brbr- Tasteful furnishings and decor brbr- Plush seating in the living room brbrbrbrDelightful Dining: brbr- Stylish dining area for memorable meals brbr- Fully equipped kitchen with top-notch appliances brbr- Perfect for culinary creations brbrbrbrProfessional Cleaning: brbr- Meticulously maintained for your comfort brbr- Attention to detail in cleanliness brbrbrbrPets Welcome!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:brbrDuring your stay at our 4-bedroom designer's dream home in Ukrainian Village, Chicago, you'll enjoy exclusive access to the entire property. This means you have the freedom and privacy to make yourself at home in every corner of this stylish retreat.brbrbrbrYour comfort and enjoyment are our top priorities, and we want you to feel at home in this designer's dream space. If you have any specific questions or requests regarding guest access, feel free to reach out to us – we're here to make your stay as enjoyable as possible.brbrbrbrThe Neighborhood:brbrThe home sits in the West Town area, about four miles west of Downtown Chicago, blending historic residential charm with the energy of a central neighborhood. The streets around here are generally walkable and lined with a mix of older homes and renovated spaces, and you’re within easy reach of local parks like Smith Park and a broad variety of restaurants, cafés, bars, and shops that help give the area a lively, urban feel. Locals describe West Town as culturally diverse and active—with plenty of dog walkers, joggers, and neighbors out and about—and though some pockets near major intersections can feel busier and safety perceptions vary block by block, most residents enjoy the convenience of public transit options and proximity to vibrant hubs like Ukrainian Village, Wicker Park, and the West Loop.brbrbrbrNearby spots to grab coffee or a casual bite include The Wormhole Coffee, Discourse Coffee, Oud Coffee & Cafe, and Star Lounge Coffee Bar, all within a short ride or walk and typical of the independent cafés that give this part of the city its neighborhood vibe.brbrbrbrGetting Around:brbrFrom O'Hare International Airport:brbr25–45 minutes depending on traffic.brbrbrbrFrom Chicago Midway International Airport:brbr25–40 minutes depending on traffic.brbrbrbrOther Things to Note:brbrCheck-In and Check-Out: Our standard check-in time is at 4pm and check-out is at 11am. We strive to accommodate your schedule whenever possible, so please let us know if you require alternative arrangements, and we will do our best to accommodate you.brbrbrbrParking: Ample free street parking brbrbrbrSmoking Policy: Our property is strictly non-smoking. Smoking is not permitted indoors, including all bedrooms and common areas. Designated outdoor smoking areas may be available; please inquire.brbrbrbrPet Policy: We allow a maximum of 2 pets for a one time fee of $150.brbrbrbrEmergency Contact: In case of emergencies or any issues during your stay, we provide a 24/7 emergency contact number to ensure prompt assistance and resolution.brbrbrbrHouse Rules: We kindly ask that guests adhere to our house rules, which may include guidelines on noise, behavior, and care of the property. These rules are in place to ensure a pleasant stay for all guests.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.brbrbrbrShared Housing Unit Operation License Number: 2823378 brbrChicago Registration Number: R23000107272brbrbrbrInteraction with Guests:brbrPrivacy and Independence: While we are available throughout your stay to assist with any inquiries or issues, we respect your privacy and understand that you may prefer independence. You'll have the entire property to yourself, allowing you to relax and enjoy your time without intrusion.brbrbrbrCommunication: We are easily reachable via phone, email, or messaging apps. If you have any questions, concerns, or require assistance, please don't hesitate to reach out. Whether it's a request for extra towels or recommendations for the best local cafes, we're here to help.brbrbrbrMaintenance and Cleaning: To maintain the high standard of our designer's dream home, we may schedule occasional maintenance or cleaning visits during longer stays. Rest assured, we will always coordinate with you in advance to ensure minimal disruption to your plans.brbrbrbrEmergency Support: In the event of an emergency or urgent issue, we provide a 24/7 contact number for immediate assistance. Your safety and well-being are of utmost importance to us.brbrbrbrFeedback: Your feedback is valuable to us. We encourage you to share your thoughts and suggestions about your stay. Your input helps us improve our accommodations and enhance the experience for future guests.brbrbrbrOur goal is to ensure your stay in our designer's dream home is enjoyable, comfortable, and stress-free. If you have any specific preferences or special requests regarding your interactions with us, please feel free to let us know. We're here to make your stay in Ukrainian Village a fantastic experience!

4

Bed

2

Bath

10

Sleeps

$564.51

/ Nightly

Private Vacation Home

Upscale Chatham Home Perfect for Families & Groups

Chicago, Illinois, United States

The Space: Comfort & Entertainment Across 3 LevelsbrbrLevel 1: Open Concept LivingbrThe main floor is centered around seamless flow from the kitchen to the front of the house.br- Gourmet Kitchen: Fully equipped with stainless steel appliances, a large island, and everything you need to cook a family feast.br- Entertainment Area: Comfortable living room seating and a smart TV, flowing directly into the entire first floor.brbrLevel 2: The Sleeping QuartersbrRetreat upstairs to your private sleeping area designed for ultimate relaxation.br- Master Suite: Features a king bed and a private, full ensuite bathroom—your own oasis after a day of Chicago fun.br- Two Additional Bedrooms: Both rooms feature comfortable queen beds and smart TV's.brFinished Basement: The Ultimate BonusbrThis versatile, dedicated space is a huge asset for groups!br- Rec Room: Perfect for kids, games, or a quiet night in.br- Fourth Bedroom & Third Bathroom brbrHigh-Value AmenitiesbrFast & Free WiFi: Reliable, high-speed internet throughout the entire house.brOnstreet Parking with optional secured parking in yard upon request.brCentral Air & Heat: Stay comfortable year-round.brSelf Check-In/out: Easy, secure keyless entry.brbr* The Location: Chicago (Chatham Area)brLocated in a quiet, residential section of Chicago, you're positioned for easy access to all the city has to offer:brDowntown Access: Convenient drive or ride-share to iconic Chicago attractions like Millennium Park and Navy Pier.brTransportation: Close proximity to major bus lines and highway entrances (I-94) for fast movement around the city.brLocal Access: Nearby grocery stores, restaurants, and parks.brGuest Access & PoliciesbrGuests have private, exclusive access to the entire 4-bedroom, 3-bathroom home.brbrPlease Note: We are committed to providing a peaceful neighborhood experience. Parties, excessive noise, and smoking inside the property are strictly prohibited.brbr**Ready to book your Chicago stay **brbrClick Book Now to secure your dates in this highly sought-after, spacious home!

4

Bed

3

Bath

10

Sleeps

$281.6

/ Nightly

Private Vacation Home

Remodeled 3 story entire townhouse available in the heart of Lincoln Park.

Chicago, Illinois, United States

Welcome to our urban oasis in Lincoln Park! Offering the entire townhouse available for your stay. The space offers 3 private bedrooms with their own private bathrooms, ensuring a delightful and exclusive stay in the heart of Chicago.brbrRoom 1:brStep into luxury at our Master Bedroom Retreat! This opulent private room features a grand, newly renovated bathroom with a lavish tub, separate shower, and toilet, providing the perfect blend of extravagance and tranquility. The room itself exudes elegance and sophistication, offering a spacious and rejuvenating escape from the city's hustle and bustle. After a day of urban exploration, immerse yourself in comfort and style in this upscale haven.brbrRoom 2 and 3:brExperience urban chic in our inviting private room, uniquely positioned on the first floor of our townhouse in Lincoln Park. This cozy yet spacious room boasts its own recently renovated full bathroom, providing a private sanctuary for your Chicago getaway. Thoughtfully designed and impeccably clean, the room offers a stylish retreat for your city adventures.brbrAll rooms provide access to the shared living room and kitchen. Additionally, take in the mesmerizing views of Chicago's iconic downtown skyline from the private deck on the third floor, where you can soak in the city's vibrant energy. Get ready to elevate your Chicago experience and make unforgettable memories in the heart of Lincoln Park!brbrLincoln Park is historic, centrally located to great shopping and dining experiences. It’s also close proximity to public transportation, west loop, and is walking distance to Lincoln Park Zoo, the Lincoln Park Conservatory, North Avenue Beach, the Peggy Notebaert Nature Museum, the Chicago History Museum, and in the warmer months, the Green City Market, all of which bring attract locals and tourists to the neighborhood.brbrNear the PREMIER ARMITAGE AVENUE RETAIL CORRIDOR Located along Lincoln Park’s main shopping corridor, the Property is surroundedbrby a powerful retail corridor, containing a balanced mix of premium restaurants, bars, and shopping.br

3

Bed

3

Bath

4

Sleeps

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