Vacation Home Rentals By Owner In Chicago, IL

Luxury 5BD Home: Sauna, Hot Tub, Rooftop, Game Rm

Chicago, Illinois, United States

Bed

Bath

Sleeps

$480.52

The property boasts an open and inviting floor plan, flooded with natural light, and luxurious finishes throughout, such as stunning hardwood floors and top-of-the-line fixtures. With its sleek and contemporary design and unparalleled level of quality, this property is the perfect choice for those seeking a high-end, modern living space in one of the most sought-after neighborhoods in the city.

Lovely three bedroom Loft, University Of Chicago, Obama Library

Chicago, Illinois, United States

Bed

Bath

Sleeps

$517.63

Welcome to The Grace Stay in Chicago!—a cozy, 3-bedroom getaway nestled in the quiet Kilbourn Park neighborhood. Whether you're in town to explore Chicago’s iconic downtown, catch a Cubs game, or day trip to Indiana Dunes, this home is your perfect launchpad.brbrGuests have full private access to the entire home—no shared spaces.brbrSelf-check‑in with a keypad makes arrival a breeze.brYou’ll also have access to:brbrBackyard and firepit area (seasonal use; instructions provided)brbrLaundry room (washer and dryer + basic supplies)brbrEV charging in our garage, text us if you need to charge your car.brbrBaby-friendly: Crib, high chair, baby utensils & dinnerware providedbrbr Location & Things to DobrbrCentrally positioned in Kilbourn Park / Logan Square, your stay is close to transit, food, and fun:brbr 10 min walk or short rides to Blue Line (Belmont/Addison) for easy airport and downtown accessbrbr 20 min to Millennium Park, The Bean, Navy Pierbrbr 15 min drive to Wrigley Field or catch the Red Line to a Cubs gamebrbr45 min drive to Indiana Dunes National Park—perfect beach escape day tripbrbr 5–10 min walk to Logan Square’s best cafés, breweries, and restaurantsbrbr 10 min to Joong Boo Market (must‑visit Korean grocery)brbr 5 min to Northwestern Medicine Immediate Carebrbr15–25 min to O’Hare by car or Blue Line

Chic 3BR King Bed+Work-Friendly+ Firepit

Chicago, Illinois, United States

Bed

Bath

Sleeps

$764.0

The Greenleaf House, built in 1915, is our 3600ft² home with 6 bedrooms, 2.5 baths, & an open floor plan—perfect for gatherings of any kind. We're in the heart of the Rogers Park neighborhood, walking distance from many restaurants & 1 block from Loyola Beach Park. Breakfast is self-serve & included in the cost of the room. In the kitchen you will find bagels, cream cheese, eggs, yogurt, cereal & fresh fruit. The home is run by friendly local folks who are happy to help during your stay.brbrYou would have access to the entire house, which has 6 bedrooms, 2.5 bathrooms, and an open, spacious first floor with a modern kitchen, large dining room (seats 12-16), living room with ample and comfortable seating, sound-insulated theater, and a big backyard that is fenced-in and dog-friendly. The house is perfect for hosting parties and events, a weekend getaway with friends or family, or gathering everybody together to celebrate a graduation or wedding. Below you will find a list of the rooms and accommodations.brbr1 King sized room (sleeps 2)br2 Queen sized room (sleep 2 each)br1 Single Sized room (sleeps 1)brTwo lofted Bunk Rooms (Sleeps 1x2) *kids, teens, small adultsbrbrTOTAL: 10 people can sleep comfortably in beds, but we also have 2 air mattresses and several couches.brbrCatering is available upon request.brbrTwo parking spaces are included—one in the front of the house, another in the rear.brbrThe entire first floor is shared space (all the bedrooms are upstairs). You will have access to: a modern kitchen stocked with complimentary breakfast items; a sound insulated theater equipped with Netflix, Showtime and an Xbox; a spacious living room with comfortable seating, a record player and a fine selection of vinyl; a dining room that seats 12-16 people; washer and dryer with free detergent/dryer sheets, and a picnic table and firepit in our big backyard which is fenced-in and dog-friendly.brbrWe like to have everything setup for you and your guests upon arrival. We will communicate with you through the app prior to your reservation to be sure of this. If something unforeseen should occur, our staff is nearby and happy to help. Otherwise, the house is all yours!brbrThe Greenleaf House has become a hub in the Glenwood Avenue Art District of Roger’s Park, where all flavors of creative artists have lived and collaborated for several decades. The Mile of Murals—a community-based public art initiative—begins half a block from our front door. Within easy walking distance you will find a bustling nightlife, small theaters and music venues, several locally-owned eateries, and Loyola Park, which has a great playground and arguably the best sand beach in the city.brbrHere are a few links about our neighborhood:brbrhttps://www.choosechicago.com/neighborhoods/north/rogers-park/brbrhttp://www.glenwoodave.orgbrbrhttps://www.rogerspark.combrbrThe Greenleaf House is conveniently located near two major public trains—we are one block from the El (CTA Red Line at Morse Avenue) and three blocks (5-8 minute walk) from the Roger’s Park Metra Station. There are several bus stops within walking distance, including express buses to downtown. It is also never difficult to hail a cab, and Uber/Lyft rides generally arrive in 1-5 minutes after placing a request. For your convenience, we have included links to public transit information below. brbrCTA Morse Red Line Station:brbrhttps://www.transitchicago.com/travel-information/rail-station/-stopid-104/brbrMetra Rogers Park Station:brbrhttps://metrarail.com/maps-schedules/train-lines/UP-N/stations/ROGERPKbrbrChecking out: Check-out time is 12pm noon. Please leave your keys in the door. brbrChecking Out late: You may checkout late till 3pm, but must be out of your room by 12pm. Feel free to hang out on the first floor, or stow your luggage and explore. If you would like to stay later than 3pm, we are happy to accommodate you so long as it doesn’t interfere with a house rental or special event. brbrLuggage Storage: There is a storage space in the TV room. It is first come, first serve and has a lock and key. If the key is in the lock, it is free to use. Please use only if your room is unavailable.brbrLaundry: Feel free to use the laundry any time except 12pm - 3pm. That is when we wash sheets and towels used by our guests. Detergent and dryer sheets are provided. brbrSecurity cameras: For your safety, there are security cameras inside the common areas and outside the property. We don’t actively monitor them unless something happens. Please do not tamper with the security cameras. brbrShared Space: The first floor is a shared space. This includes the TV room (which has Netflix). Feel free to hang out and interact with other guests. brbrDogs: Dogs are allowed for an extra $10 per night. We accept Venmo, PayPal, cash or check. See the dropbox in the kitchen for further instructions.brbr100% Smoke Free: Smoking is prohibited inside the house. Please smoke outside. brbrParking: Parking spots are $10/night when available. They cannot be reserved on the app. Ask your host about availability. We accept Venmo, PayPal, cash or check. See the dropbox in the kitchen for further instructions.brbrVisitors: Visitors are allowed on the first floor until 11pm.brbrQuiet Hours: As courtesy to other guests, quiet hours are 11pm to 7am.

The Greenleaf House—Whole House

Chicago, Illinois, United States

7

Bed

2

Bath

12

Sleeps

$169.67

Near Public Transit | 2 Mi to University of Chicago | Shared BackyardbrbrRestore your work/life balance with a long-term stay at this 3-bedroom, 1-bath duplex home in Chicago. Whether you're here for leisure, business, or scholastic endeavors, you can easily access the best of the city from this vacation rental. Visit the Museum of Science and Industry in Hyde Park, catch a White Sox game at Rate Field, or enjoy the lush beauty of the Garfield Park Conservatory. Start planning and book today!brbr-- THE PROPERTY --brbrSLEEPING ARRANGEMENTSbr- Bedroom 1: 1 queen bedbr- Bedroom 2: 1 queen bedbr- Bedroom 3: 1 full bedbrbrMAIN FEATURESbr- Shared backyard (fenced)br- 2 Smart TVsbr- Dining tablebrbrKITCHEN br- Stove/oven, refrigeratorbr- Microwave, dishwasherbr- Keurig coffee makerbr- Cooking basicsbr- Dishware/flatwarebr- Trash bags & paper towelsbrbrGENERAL br- Free WiFibr- Washer & dryerbr- Central heating, wall A/C unit, ceiling fansbr- Linens/towelsbrbrFAQbr- Quiet hours (8:00 AM-8:00 PM)br- 2 exterior security cameras (facing out)br- Additional vacation rental on-site (lower unit)brbrACCESSIBILITYbr- Single-story duplex homebr- Upper-level unit, stairs to enterbrbrPARKINGbr- Street parking (first-come, first-served)brbr-- THE LOCATION --brbr- 4-9 miles to Downtown Chicago attractions: Shedd Aquarium, Buckingham Fountain, The Art Institute of Chicago, Chicago Riverwalk, Navy Pier, Lincoln Park Zoo br- 1 mile to Lakeshore Drive & Oakwood Beachbr- 2 miles to Rate Field & 3 miles to Soldier Fieldbr- 2 miles to Washington Park & 5 miles to Millennium Parkbr- 2-5 miles to McCormick Placebr- 8 miles to United Centerbr- 1 mile to Northwestern Medical Center & 2 miles to University of Chicago Medicinebr- 8 miles to Chicago Midway Int'l Airport & 25 miles to 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- Must be at least 21 years old to bookbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbrbrADDITIONAL INFORMATIONbr- This single-story duplex home is located on the upper level and requires stairs to enterbr- There is an additional vacation rental on-site, in a completely separate unit on the lower level; other travelers may be present during your stay. The fenced backyard is sharedbr- Your safety matters. This property features 2 exterior security cameras: 1 camera is located on the front of the building facing out, and 1 camera is on the back of the building facing out. The cameras are outward facing and do not look into interior spaces. The cameras actively record video and sound while guests are in residence

Walk to Chicago's Shops & Eats: Bronzeville Duplex

Chicago, Illinois, United States

Bed

Bath

Sleeps

$676.13

Step into vintage charm at Maison Winona, a 1908 Prairie School stunner by Chicago architect Frederick Schock, in the heart of Andersonville. With interiors that whisper ooh là là, Maison Winona blends boutique comfort with a maximalist vibe. Enjoy a lush private balcony, and free street parking. A 10-min stroll brings you to Lake Michigan, the Green Mill, Chicago Magic Lounge, and Clark St’s top restaurants. Perfect for families, friends, and bon vivants seeking a one-of-a-kind Chicago stay.brbrPARKING - Free Street ParkingbrbrThe spacebrPRIME LOCATIONbr- 6 min walk to Redline Argyle Station/SunWah BBQ/Yoo Yeebr- 9 min walk to Clark St (Over 80 Restaurants, Cafes, Shops)br- 12 min walk to Lake Michigan (Foster Beach)br- 9 min walk to Green Mill/Riviera/Aragon BallroombrbrNearby Universitiesbr- Loyola: 7 min drivebr- Northwestern: 21 min drive br- DePaul: 16 min drive brbrBEDROOM 1 (Primary)br- King bedbr- Hotel quality linensbr- Vintage Chaise Loungebr- Walk-in closetbr- ACbr- Ceiling fanbr- Full Length mirrorbr- Luggage rackbr- Ensuite bath with walk-in shower & thermostatic systembr- Spa tub inside walk-in showerbr- Dedicated workspace with LED vanity mirrorbrbrBEDROOM 2br- Queen bedbr- Hotel quality linensbr- Blackout curtainsbr- Ceiling fanbr- Closetbr- Mirrorbr- Bedrooms 1 & 2 share a hallwaybrbrLIVING ROOM 2 (Flex Room)br- Day bed with queen size-trundlebr-Balcony accessbr- When fully extended, the trundle fills most of the room — still walkable, just snugbr-Low-profile bed sits directly at floor level — a slumber party feel with grown-up stylebrbrLIVING ROOM 1 & ENTERTAINMENTbr– Seats 6 (sofa, loveseat, vintage chairs)br– Decorative (non-working) fireplacebr– 65 LG Smart TVbr– Hulu & Disney+ (No Ads) providedbr– Use your own login to access a variety of streaming apps br– Samsung Bluetooth soundbar systembr– AC br– 2 Gbps high-speed Wi-FibrbrDINING ROOMbr- Vintage Dining table seats 6br- Cocktail cart with shaker, tools & ice bucketbrbrCOFFEE & TEA READYbr- Coffee bar with drip + French pressbr- Local Whole Bean Coffee, creamers, & sweetenersbr- Pour-over tea kettle + tea selectionbrbrKITCHEN + BUTLER'S PANTRYbr- Fully equipped Kitchen with quartz countertopsbrOther things to notebrbrBATHROOMbr– Clawfoot tub/shower combo (porcelain)br– Grab bars for entry/exitbr– Tub is shorter than standard and requires high step-inbr– Towels: 2 of each (bath, hand, washcloth) per guestbr– 2 Conair InfinitePRO hair dryersbr– Aveda Rosemary Mint: shampoo, conditioner, body wash, hand soap, lotion (starter supply – 12 oz each)brbrBEACH GEARbr– 6 beach towels, 3 queen-size mats, 6 beach bagsbr– 1 beach wagonbr– 2 Titan backpack coolers, 1 Igloo wheeled coolerbr– 6 reusable Titan ice packsbrbrPRIVATE COVERED 2ND FLOOR BALCONYbr– Seats 6brbrOPEN 1ST FLOOR BALCONY (SHARED)br– Seats 5brbrCAMERASbrThere are 5 exterior cameras:br- Doorbell camera at the front doorbr- One on the second floor balconybr- One on the first floor balconybr- Two in the backyard brbrEARLY CHECK-IN OPTIONSbrEarly arrival is available for 75% of the average daily rate or your reservation if approved. Message us 24 hours in advance. Not available if another guest has booked or if maintenance is scheduled.brbrLATE CHECK-OUTbrLate check-out is contingent on turnover needs. In the event that it is available, the rate is 75% of the average daily rate of your reservation. Please ask if interested.brbrPARKING DETAILS:br– Free street parking (limited 6 PM–8 AM)br– Paid street parking via ParkChicago appbr– Paid nearby options via SpotHero appbr– No on-site parkingbrbrTransportationbr– Uber/Lyft: typically 3–5 min waitbr– CTA Red Line: every 3–9 min (day), 15–20 min (night); operates 24/7br– Divvy bike rental station nearbybrbrFrom O’Hare (ORD) (~1 hr 15 min):br– CTA Blue Line from terminal toward Forest Parkbr– Transfer to Red Line at Jackson (walk one block east)br– Red Line toward Howardbr– Exit at Argylebr– Walk 2 min west on Argyle. Walk 3 min north on Broadway. Walk 1 min west on Winona. Maison Winona is directly West of the Dunkin Donuts.brbrFrom Midway (MDW) (~1 hr):br– CTA Orange Line toward Loopbr– Transfer to Red Line at Rooseveltbr– Red Line toward Howardbr– Exit at Argylebr– Walk 2 min west on Argyle. Walk 3 min north on Broadway. Walk 1 min west on Winona. Maison Winona is directly West of the Dunkin Donuts.brbrRental Agreement (Required)br– After booking, guests complete a rental agreement outlining house rules, occupancy limits, confirmation that unregistered overnight guests as well as unannounced guests are not permitted, check-in/out procedures, and Chicago’s Shared Housing Ordinance requirements.br________________________________________brAbout the SpacebrbrGuest Private Spacesbr– Entire second-floor apartment with covered balconybrbrShared Spacesbr– First-floor balcony brbr– Front entry & hallway – Shared; you may see us or our guests occasionally. We aim to be quiet and courteous—merci for doing the same!brbr– Back stairwell – Accessible via backyard. Our 2 resident cats may greet you—they're friendly and nosy.brbrHost’s Private Spacesbr– Backyard – Private; not available to guests (City of Chicago prohibits food/alcohol sharing).brbr– Grill – Not for guest use.brbr– Visibility – Backyard may be seen from Bedroom 2, back stairwell, and storage room. Sound may carry lightly.brbr– Driveway — Guests may use the driveway for check-in and check-out only. It’s reserved for host use at all other times. Free street parking is available. Vehicles parked in the driveway during a stay risk being towed.br________________________________________brHouse Rules Agreementbr– Booking our property equals guest agreement to comply with House Rules and the rental agreement.br– Violations may result in:br– Notification to VRBO and/or local authoritiesbr– Booking termination without refundbr– Guest liability for damages, fees, legal expensesbr________________________________________brOptional Add-Onsbr– Early Check-in / Late Arrival – 75% of average daily rate (when approved by host)br– Lost Item Return – $150/item for domestic shipping (restrictions apply – see House Rules)br– Cleaning during stay $275 when available. Must request 36 hours in advance. Payment in full required to reserve this service.

Chic Vintage Stay w/ Private Balcony – Walk to Argyle Redline, Lake, Dining

Chicago, Illinois, United States

2

Bed

1

Bath

6

Sleeps

$2222.48

Open concept floor -kitchen with dining space along with two living rooms with TVs, basement includes indoor heated pool along with game room and seating area with TV. Third floor has three bedrooms each updated with king size beds. Third floor has one full bathroom .

Spacious family size home with indoor pool

Chicago, Illinois, United States

Bed

1

Bath

7

Sleeps

$270.59

Make yourself at home in this 3-bedroom Chicago retreat. This charming house offers all the comforts you need for a wonderful stay, including WiFi, AC, and a washing machine. With 2 bathrooms and cozy bedrooms, guests will have plenty of space to relax and unwind. Our place will help you feel at home while you're traveling in Chicago.

Charming 3-bedroom house with AC and WiFi in awesome Chicago

Chicago, Illinois, United States

Bed

Bath

Sleeps

$270.73

Escape to this fabulous house in picturesque Chicago. With 3 bedrooms including 2 queen beds and 1 full bed, this cozy retreat is perfect for families or groups of friends. Enjoy the convenience of amenities like WiFi, a washing machine, and more. Relax in the 3 bathrooms equipped with a hair dryer. We hope you enjoy what our place and Chicago has to offer.

Charming 3-bedroom house in amazing Chicago

Chicago, Illinois, United States

Bed

Bath

Sleeps

$841.52

Welcome to our Remodeled 3 Bedroom, 3-Bathroom Family Home in the Heart of East Rogers Park on the North side of Chicago (one mile from the walking paths and beaches of Lake Michigan).brbrStep into a bright and inviting open space on the first floor, flooded with natural light, perfect for gatherings and relaxation. Our recently renovated home boasts a modern aesthetic with a spacious layout, ideal for families or groups.brbr**Key Features:**br- Open floor plan br- The kitchen features quartz countertops, dishwasher, and a full fridge and freezer - plus everything you'd need to create your culinary masterpiece. Microwave, coffee maker, utensils, high end cutlery, spices, pots, pans, serving ware, blender, and more. br- 3 Bedrooms: Ample sleeping space for your entire party.br- 3 Full Bathrooms: No need to wait – everyone can get ready at their own pace. One bathroom features a vintage claw foot tub - perfect for the kids. br- Master Suite: Enjoy the luxury of an en-suite bathroom in the spacious master bedroom with a king size bed.br- Natural Light: Large windows illuminate the open first-floor area, creating a warm and welcoming atmosphere.br- Double Lot: Our home sits on a double Chicago lot, providing an expansive multi-purpose yard for your enjoyment.brbr**Location Highlights:**br- Proximity to Lake: Explore the nearby lakeside beauty with ease. Approximately 1 mile walk. br- Public Transit: Convenient access to public transportation for hassle-free travel around the city. Our home is conveniently located near downtown Chicago and very accessible by train. We are 0.1 miles from the Union Pacific North Metra line - 2 minute walk. The CTA Red Line (Morse) is 0.7 mile - 12 min walk. Access to multiple bus lines within a few minutes of walking (22, 151, 155, 96). brbr**Perfect for Groups and Families:**brWhether you're in town with family or friends, our home is designed to accommodate your needs. The large open spaces and multi-purpose yard make it an ideal choice for group activities and family bonding.brbrBook your stay today and experience the comfort and convenience of our Chicago home!

Spacious home w Chef’s Kitchen, Natural Light, Open Floor Plan, Ideal for Groups

Chicago, Illinois, United States

Bed

Bath

6

Sleeps

$729.03

Summary:brbrWelcome to our stunning 4-bedroom retreat in Chicago. brbrbrbr- Comfy living area with natural light brbr- Inviting atmosphere for socializing brbr- Fully equipped kitchen and dining area brbr- Cozy bedrooms with plush bedding brbr- Central location near cafes and boutiques brbrbrbrBook your stay with TheDreamRentals today!brbrbrbrThe Space:brbrAs you step inside, you'll be greeted by a stylishly decorated living area that exudes warmth and sophistication. The open-concept living area is ideal for socializing or unwinding after a day of exploring the vibrant neighborhood. brbrbrbrComfortable Accommodation:brbr- Four cozy bedrooms brbr- Three bedrooms with queen beds and one double bunk bedbrbr- Thoughtfully furnished with plush beddingbrbr- Storage space for your belongingsbrbrbrbrInterior Feeling:brbr- Stylishly decorated living areabrbr- Abundance of natural light from large windowsbrbr- Contemporary decor creating a bright and inviting atmospherebrbrbrbrDelightful Dining:brbr- Fully equipped kitchen for aspiring chefsbrbr- Stylish dining area for enjoying meals togetherbrbrbrbrProfessional Cleaning:brbr- Meticulously maintained for your comfortbrbr- Ensures a welcoming and hygienic environmentbrbrbrbrBook 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 exclusive access to the entire apartment during their stay, ensuring privacy and comfort.brbrbrbrEnjoy full access to all four bedrooms, the spacious living area, fully equipped kitchen, and dining space.brbrbrbrMake yourselves at home with amenities such as high-speed Wi-Fi, smart TV with streaming services, and a washer/dryer for added convenience.brbrbrbrThe Neighborhood:brbrRiverWest offers the best of both worlds: a welcoming residential feel with quick access to downtown’s restaurants, shopping, nightlife, and attractions. Public transportation and major highways are nearby, making it simple to get anywhere you want to go.brbrbrbrGetting Around:brbrFrom O’Hare International Airport (ORD):brbrBy car/taxi/ride-share: About 30–40 minutes depending on traffic. Take I-90 East toward downtown, exit at Ogden Ave, and head toward RiverWest.brbrBy CTA train: Take the Blue Line toward Forest Park. Exit at Chicago Avenue or Grand Avenue stations — both are about a 10–15 minute walk to most RiverWest addresses.brbrbrbrFrom Midway International Airport (MDW):brbrBy car/taxi/ride-share: About 25–35 minutes depending on traffic. Take I-55 North toward downtown, connect to I-90/94 West, and exit near Ogden Ave or Chicago Ave for RiverWest.brbrBy CTA train: Take the Orange Line to Clark/Lake, then transfer to the Blue Line toward O’Hare. Exit at Chicago Avenue or Grand Avenue stations.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 the penthouse. Please smoke outside.brbrbrbrPet Policy: We adore pets, but unfortunately, the penthouse 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 penthouse is as indicated in your booking details. Hosting additional overnight guests without prior approval is not permitted.brbrSecurity: 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.brbrbrbrRegistration number: R24000116981brbrShared Housing Unit Operation License Number: 2823378brbrbrbrInteraction with Guests:brbrPrivacy Respected: While we're available to assist you throughout your stay, we respect your privacy and understand that you're here to relax and unwind. Enjoy the penthouse as if it were your own private haven.brbrbrbrSupport 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.

River West 4BD Home: Perfect for Families & Groups

Chicago, Illinois, United States

Bed

Bath

Sleeps

$360.63

Your home away from home in Chicago with 3 adorable queen bedrooms. This charming house offers WiFi, a washing machine, iron, hair dryer, and AC for your convenience. Relax in the tranquil ambiance of this cozy retreat. Enjoy all that Chicago has to offer when you stay at our place. # Charming 3BR/2BA in Bronzeville - Close to Downtown!brExperience Chicago in our cozy 3-bedroom, 2-bathroom home in historic Bronzeville. br- 9 minutes from downtownbr- Near Green Line stationbr- Close to Lake Shore Drive and 31st Street Beachbr- 3 bedrooms, 2 bathroomsbr- Spacious living areasbr- Fully equipped kitchenbr- Free street parkingbr- Paid parking for small cars (extra fee)brEnjoy Bronzeville's culture with easy access to Chicago's attractions. Book for a memorable Windy City stay

Breeze of Bronzeville Chicago: 3 bedroom 2 bath 9 mins from downtown chicago

Chicago, Illinois, United States

Bed

Bath

Sleeps

$208.52

Welcome to our cozy Vrbo in the vibrant city of Chicago. Situated conveniently between O’Hare airport and downtown. Our charming home offers 2 comfy bedrooms with queen beds, spacious living and dining rooms, and a newly renovated kitchen!brbrWell connected via Chicago transit; explore the amazing food scene and nearby parks and attractions.brbrTransit - bus stop outside takes you to the blue, brown, and red lines. Free street parking; drive 20 min to Willis Tower and 13 min to Wrigley Field.brbrThe Spacebrbr-Private 2-bedroom, 1-bath apartment located on the 2nd floor of a traditional Chicago two-flatbrbr-Guests must climb one flight of stairs to access the unitbrbr- Entire apartment is private and exclusively available for your staybrbr-Smart TV with streaming apps available (guests use their own logins)brbr-Fully equipped kitchen with cookware, dishes, Keurig coffee machine, toaster, microwave, stove/oven, and refrigeratorbrbr-Clean linens, towels, shampoo, conditioner, body wash, and starter supplies provided prior to arrivalbrbr-Free street parking available nearby on a first-come, first-served basisbrbr-Washer and dryer are located in the basement and are shared with the other units in the building. Access is through the back stairwaybrbr-Please note this is a multi-unit residential building, so occasional neighbor noise may be heardbrbr-Chicago quiet hours must be observed between 10pm–8am dailybrbrGuest Accessbrbr-Guests will enter through the front entrance and access their own private apartmentbrbr-Check-in instructions and access codes will be provided prior to arrivalbrbr-Early Check In is available for an additional charge of $50, but is subject to availability. Please message the host to confirm.brbr-Late Check Out is available for an additional charge of $50, but is subject to availability. Please message the host to confirm.brbrOther Things To Notebrbr- Absolutely no parties, gatherings, unauthorized guests, or smoking of any kind are permitted on the propertybrbr- Violation of house rules may result in additional cleaning or damage fees of up to $400 and immediate cancellation of the reservation without refundbrbr-Outside decorations including confetti, glitter, balloons, candles, streamers, banners, or wall adhesives are not permittedbrbr-Starter supplies are provided but guests may need to replenish additional items during longer staysbrbr-Please report any issues during your stay as soon as possible so we can address them promptly. However please keep in mind that our availability is limited during after hours between 10pm-9ambrbr-Please remember this is a home and not a hotel. We strive to provide a clean, comfortable, and enjoyable stay for every guest

Cozy 2 Bedroom Home Near Downtown & Wrigley Field

Chicago, Illinois, United States

Bed

Bath

Sleeps

$1656.84

Welcome to the ultimate Disco Cowboy getaway! This huge house is perfect for bach parties and friends/family trips! Located in Wrigleyville, you can walk to Cubs games, bars/restaurants, & vibrant nightlife!brbr* Sleeps 16 comfortably - 8beds/3bathroomsbr* 2 free parking spots, plus plenty of free parking down Paulinabr* Air hockey, ping pong, basketball, bowlingbr* Tons of space for everyone to spread outbr* 18 min walk to Wrigley Field & Gallagher Waybr* 2 min walk to coffee shops, restaurants, & bars br* 23 min from O'hare Airportbr* 35 min from Midway Airport

Retro Disco Cowboy Fun, Walk to Wrigley, Restaurants/Bars! 15 mins to downtown!

Chicago, Illinois, United States

Bed

Bath

Sleeps

$1164.1

The Wrigleyville VIP is our 2nd Wrigleyville Vacation Rental location and #1 with our guests. The Wrigleyville VIP is located just one block away from Gallagher Way plaza and the 3rd base or Right field entrance to Wrigley Field. Live like a local in this beautifully remodeled graystone. All the best of Chicago right outside your front door. Chicago License # HM15504brbrEasy Transportation-the 'L' Red line 2 blocks, Brown line 3 Blocks. Cabs/Uber on street. Easy to take the train from O'Hare or Midway Airports.brbr*Need parking Neighborhood parking passes included. Street parking is easy at this location with the exception being 2 hours before and after games/events at Wrigley. If you will be visiting during a Cubs home stand or other Wrigley Field event and would like a reserved parking spot please let us know in advance. We do have access to a limited amount of discounted reserved parking spots for our guests.brbr**Larger groups please check availability of The Wrigleyville Deluxe- Sleeps 10; VRBO 2468294. Also check The Original Wrigleyville Coach House; vrbo.com listing 376945. (300+ 5 Star reviews) is perfect for groups of 6-10 as well.brbr*** Need Tickets Ask us about Cubs Tickets- 200 level; several prime sets of 3-8. We also have a trusted local relationship to help you find tickets in other sections along with Wrigley Concert tickets, Bears, Sox, Blackhawks, Bulls tickets.brbr**Looking for a longer/shorter stay, more or less guests, while in Wrigleyville Sometimes we are able to make exceptions to our minimum requirements, please ask!brbrLiving roombrbrModern Kitchen with Granite Counters and Custom Cherry Cabinetsbrbr1 King Bed in Master Suitebrbr2 Queen Beds in Bedroom 2brbr2 Full Bathroomsbrbr1 Sofa sleeperbrbrSatellite TV and WiFibrbr2 New Flat Panel HDTV’sbrbrGroceries- Jewel is a quick walk to Southport just 3 blocks away.brbrCoffee- Local coffee shops and bakeries nearby along with Starbucks and Dunkin Donuts a few blocks in any direction its easy to get your coffee fix.brbrBreakfast, Lunch-Tons of local establishments nearby on Clark and Addison or on Southport.brbrDinner- Tons to choose from in the neighborhood within walking distance. OR- take the train to State and Rush for Gibson's OR quick cab to Lincoln Park. There are so many choices In Wrigleyville. Please let us know if we can help you find the right dining spots for your occasion.brbrPizza- Several to choose from in the area. Our favorite is D'Agostino's located on Southport just down the street a few blocks away.brbrEntertainment-brExperience the Windy City the VIP way! All the city has to offer is just outside your door. Head to Clark Street and explore all that is Wrigleyville. Head West a couple blocks and explore the Southport Corridor for a more local feel. Walk to coffee, breakfast, lunch and dinner, bars, pubs, patio restaurants, parks, splash parks, ice skating in the winter, movies, theatre, bowling, groceries, local shopping, high end retail, and much, much more.brbr-Visit Lake Shore Drive and walk the Lincoln Park Zoo- greatest Free Zoo in the Country.brbr-Go to the Beach.brbr-Go to a local street festival.brbr-Take the kids to one of many neighborhood parksbrbr-Hit the splash park at Gallagher way.brbr-Go to a concert or movie in the parkbrbr-Go Ice Skating at Gallagher way in the winter.brbr-Bowling- The Lucky Strike bowl and arcade is a 5 min walk and awesome. brbr-Take the train to Millennium Park, Grant Park, Willis Tower or John Hancock.brbr-Quick cab to Second City or The Blue Man Group. Cab or Train to the Theatre district.brbr-Walk Southport Ave. Shop-Eat-Drink!brbr-Explore the neighborhood around Clark and Addison even if the CUBS are not in town.brbrGallagher Way, The Hotel Zachary, all of the new restaurants like Smoke Daddy’s, Big Star, Rizzo's along with favorites like Bernies, and the Cubby Bear are all minutes away.brbrKeywords: Ryder Cup, Golf, Last Minute, Location, This Weekend, Large Groups, Wrigley, Bears, Cubs, Northwestern Wildcats, Blackhawks, Games, Special Occasions, Concerts, Festivals, Lakeview, El,L,Brown Line, Redline, O'hare, Midway, Lakeshore, Lincoln Park, Wedding, Bachelor, Bachelorette, Bar, Restaurant, Public Transportation, Private, City,Train,Clean, Southport, Clark, Addison,Airport,House, Wrigleyville

The Wrigleyville VIP- Luxury unit, a block from Wrigley Field, Cubs Fan Favorite

Chicago, Illinois, United States

Bed

Bath

Sleeps

$421.05

Comfortable, renovated, stylish and very clean house with 3 BR (total 5 beds) and 2.5 BTH in a quiet area of Chicago. Excellent location: 4 miles (8 min) from ORD and 17 miles from downtown Chicago (20min), Forest Preserve across the street. Only 2 miles from expressways. Close to public transit. NO PARTY AND SAME CITY BOOKING ALLOWED. No pets.

Family Home in Chicago-O'Hare

Chicago, Illinois, United States

Bed

Bath

Sleeps

$658.08

Beautiful bright & sunny Wicker Park 3 bedroom, 2 bath 1,500 square foot apartment located on the top floor of a private home. This unit is located just one block away from the Damen Blue Line el subway station in the heart of the vibrant Wicker Park/Bucktown neighborhood. Less than 5 minute walking distance to some of the hottest restaurants, bars, and boutiques in Chicago. Located on a historic tree-lined street in a landmark district, our property is steps away to one of Chicago's coolest entertainment districts known for its local hipster culture, art community, nightlife, and food scene. You will have the privacy and quiet of a street filled with historic mansions in the old Beer Baron Row district. We are on the border of Bucktown; nearby neighborhoods include Ukrainian Village, Logan Square, and Lincoln Park. We are only 15 minutes from downtown Chicago; a 5 minute walk to the 606 Biking/Walking trail; 2 blocks from beautiful Wicker Park green space with children's park, gardens, baseball diamond, basketball court, etc.brbrThe unit has several distinct features including vaulted ceilings, stained glass, exposed brick, fireplace, 65 flat screen TV in the living room, large laundry room with in-unit washer and dryer, and a small deck to enjoy a cocktail. The space is the top 3rd floor of an 1893 Greystone that we rehabbed to contain today's modern luxuries but retain the historic charm of the neighborhood.brbrThe unit is accessed through a side gate and up through a back deck to get to the third floor. brbrStreet parking out front is free; potential garage parking spot available for an additional fee. brbrLonger term rentals allowed.brbrThis is a family home so we ask NO parties on premises. brbrLayout of unit: br1 bedroom with queen bed and in-suite bath including bathtubbr1 bedroom with queen bed br1 bedroom with queen bed br1 common bathroom with double vanity and shower/bathtubbrLaundry room with washer and dryerbrKitchenette type kitchen with stainless steel refrigerator, dishwasher, stove, and small wine fridgebrLarge gas fireplacebrbrAmenities: A/C, Wifi, Cable TV and Netflix, Coffee Maker, Microwave, Dishes & Silverware, Cooking Basic Utensils, Extra Pillows/Blankets, Pack 'n Play Crib, Air Mattress, Shower Supplies including Shampoo, Conditioner, etc.brbrThe restaurant and bar scene in the neighborhood is unlimited and ever changing. We are happy to provide our favorite places and recommendations at time of reservation. brbrEnjoy an amazing week or weekend in one of the most exciting neighborhoods Chicago has to offer!

Wicker Park 3 Bedroom. Top floor Historic Greystone. Near Damen El Stop.

Chicago, Illinois, United States

Bed

Bath

Sleeps

$1245.05

This amazing single-family home in the heart of Lincoln Park is steps to popular restaurants and bars, upscale boutiques as well as the L train and the Salt Shed concert venue.brbrNewly furnished and painstakingly cared for, your every need will be taken care of. Everyone will love relaxing in the rec room with the pool, ping pong, foosball, plus two classic arcade machines. brbrOur space is perfect for hosting family and friends under one roof. Come experience the best of Chicago this year.brbrOur single-family home is a spacious spot in an amazing neighborhood. Steps to the Steppenwolf Theater, Second City, Improv Olympic, The Salt Shed concert venue, numerous restaurants and bars, Whole Foods, Trader Joe's, world class dining with Alinea and BOKA, the Red Line and Brown Line, and some of the city's finest parks. It's also a quick walk down the block to the DePaul University campus. For families looking for activities for the kids, we are located less than a half-block away from three different playgrounds and walking distance to the free Lincoln Park Zoo and Chicago's beautiful lakefront.brbrThe house has hardwood floors throughout, high ceilings, a master suite and amazing light exposure. The kitchen features beautiful quartz counters and stainless appliances. The dining table is perfect for larger groups and is great for simple breakfasts on the go or celebratory group dinners.brbrEvery detail was considered when designing the space and you will have plenty of room to spread out. The basement rec room features a foosball table, a 8 foot slate pool table that converts to a ping pong table, two classic arcade machines that feature many classic games. brbrThere are three bedrooms on the second floor and one off the lower floor rec room. The upstairs features two full bathrooms with another full bathroom next to the rec room bedroom. There is also a queen-sized pullout couch in the basement. brbrOur home is on three levels, with stairs up and down from the main level. The house has hardwood flooring throughout each of the three levels and the bottom floor features full-size windows with good light. We have six queen-sized beds and one queen-sized pullout couch in the basement rec room. brbrIf the interior doesn't have you hooked yet, the location will! Lincoln Park is one of Chicago's most vibrant neighborhoods, home to award-winning restaurants, fun nightlife, world-renowned theater, and plenty of retail therapy opportunities. And our home is in the perfect location to access it all! The Salt Shed concert venue, Lincoln Park Zoo, Second City Comedy Club, and North Avenue Beach are an easy walk. Trader Joe's and Whole Foods are steps away. Red and Brown Line L trains are nearby for quick access to Wrigley Field or Downtown. Shopping from Apple Store and Nordstrom to award winning restaurants Alinea and Boka are down the street.brbrPublic transportation is plentiful as the Red, Brown and Purple Line trains are a quick two block walk and the house is a half-mile from the Clybourn Metra Stop. We also have a Divvy bike share station directly across the street -- daily rates are available and it's a great way to see the city like a local.brbrTwo blocks from either the Brown or Red line stops, you can easily be at Wrigley Field for a Cubs game or Guaranteed Rate Park to take in a White Sox game in no time. Looking for a home base during a convention McCormick Place is a 15-minute car ride away or easily accessible via the Red Line (exit at Cermak/McCormick Place). Our unique home is walking distance to everything -- from popular restaurants and bars to upscale boutiques and stores as well as public transportation and DePaul University. brbrHere is a sampling of what is at your fingertips:brbrCONCERT VENUES: We are a five minute walk to The Salt Shed and a fifteen minute walk to the Park West and Lincoln Hall. The Metro, Vic, Aragon, and Riviera are all easily accessible via the Red Line or a short Uber ride.brbrSPORTS (and sometimes concerts): Our Red Line stop is just 3 stops from Wrigley Field going north or 7 stops to Soldier Field going south and Guaranteed Rate Field is 2 additional stops beyond the Soldier Field stop. The United Center does require switching from the Red Line to the Green or Blue line. All the above are easily accessible taking a 10-15 minute Uber ride.brbrSHOPPING: If national chains aren't your thing there are tons of small boutique shops all along Armitage Avenue. But if you do like the chains - we have you covered too! Steps from Whole Foods, Trader Joes, Mariano's, Apple Store, Banana Republic, Crate and Barrel, Ulta, World Market, Sephora, Anthropologie, Williams-Sonoma, Pottery Barn, Nordstrom Rack, Moosejaw, West Elm, Dick's Sporting GoodsbrbrRESTAURANTS: Steps from world-famous and 3 Michelin Star Alinea as well as one star Boka, Esme and Galit, as well as Armitage Ale House, Old Pueblo Mexican, Summer House Santa Montica, Cafe Ba-Ba-Reeba, Blue Door Farm Stand, Ramen-San, Epic Burger, Sai Café, Home Slice, Tarentino, Butcher and the Burger, Sweet Green, Protein Bar, Chipotle, Buffalo Wild Wings, Protein Bar, Earl's Kitchen, and many more!brbrTHEATERS: Steps from Improv Olympic and Steppenwolf Theater; short walk to Second City, ZaniesbrbrPUBLIC TRANSPORTATION: Steps from North Ave Red Line and Armitage Brown Line, across the street from Divvy stationbrbrLincoln Park in Chicago is an active, energetic neighborhood full of young professionals. It is a prestigious, upscale area with huge multi-million dollar single-family homes, two flats, and three flats. The side streets are tree-lined, quiet, and quaint. But the surrounding nightlife is lively and there are many great neighborhood restaurants and bars. You have a short five-minute commute to downtown Chicago by L train. You can't beat this neighborhood for luxurious, safe living combined with excitement and fun.brbrYour family and friends will feel right at home from the moment you arrive; no detail has been overlooked.

Entire Home in Lincoln Park - Amazing Game Room - Perfect Location

Chicago, Illinois, United States

4

Bed

Bath

14

Sleeps

$301.2

Luxury 3-Bedroom Home with Themed Rooms & Private Party SpacebrWelcome to your ultimate getaway! This newly renovated luxury home offers the perfect blend of fun, comfort, and style. With flexible booking options, you can rent the space as a one-bedroom ($150/night), two-bedroom ($200/night), or the full three-bedroom experience ($300/night). A two-night minimum stay is required.brbrProperty Highlightsbr* Pac-Man Bedroom: Step into nostalgia with a high-end Pac-Man-themed room featuring two beds, a flat-screen TV, a Google Home system, and a luxury design. Perfect for gamers and fans alike!brbr* Modern Adult Bedroom: This sleek room includes a comfortable bed, two nightstands with modern lamps, a flat-screen TV, and a walk-in closet with mirrored doors.brbr* Victoria’s Secret/Barbie-Inspired Bedroom: Indulge in luxury with this beautifully designed room featuring two beds, vibrant accents, and a glamorous aesthetic.brbrEach bedroom is secured with a keycode system, offering privacy for groups renting fewer than three rooms. Luxury LED lights in each bedroom brbrAmenitiesbr* Spacious Living Room: Relax in a chic, comfortable space featuring a selfie wall and modern gray walls with beautiful textures. A brand-new hardwood floor adds to the luxury—no shoes are allowed indoors, but shoe covers are provided.br* Fully Renovated Kitchen: Cook like a pro with a stainless steel refrigerator, over-the-range microwave, and brand-new cabinets and sink. A kitchen table is available for dining.br* Private Backyard: Enjoy a fenced-in backyard for gatherings or quiet relaxation. Please note, no loitering in front of the house is permitted, with fines enforced for violations.brAdditional Featuresbr* High-Speed Internet: Stay connected throughout the property.br* Air Mattress: Accommodates extra guests, bringing the total sleeping capacity to 5 beds + 1 air mattress.br* Basement Party Space: Host your special events (repass, bridal shower, birthday party, etc.) in a spacious basement equipped with tables and chairs.br * Party Fee: $500 (requires approval)br * Unauthorized Party Fee: $750 plus a cleaning feebr * Cleaning Fee: Flat rate of $75brHouse Rulesbr* Minimum Stay: 2 nightsbr* Smoking: No cigarette smoking indoors; 420-friendly with proper cleanup.br* Furniture & Floors: Damage to floors or burns on furniture/bedding will incur fees ($100 per burn; scratches priced per repair).br* Remote Controls: Must be returned to their designated Velcro holders after use.brThis property offers the perfect setting for families, small groups, or anyone seeking a luxury stay with flexible room options and unique themed designs.brBook now and experience this unforgettable home!brbrbrbrbrThe property offers heating, WiFi, and a washing machine for convenience. We're happy to assist with any questions while you stay at our house.

Luxury 3-Bedroom Home with Themed Rooms & Private Party Space

Chicago, Illinois, United States