
House vacation rentals in Chicago
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Top-rated house rentals in Chicago
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Vacation rentals for every style
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Popular amenities for Chicago house rentals
House rentals with a pool

2-Acre Highland Park Retreat with Heated Pool ~ 5*
We were in town for Thanksgiving visiting family with our dogs for 4 nights. Communication with host was great. The house was very clean, well furnished (we cooked the Thanksgiving meal there), recently renovated kitchen (huge kitchen island) with high end appliances, and yes there are 6 bedrooms (some small but nice). Rooms are split between three floors so everyone had room/privacy. Backyard with pool was great, lots of space for dogs, everything is fenced in but the front which was not a problem as the house is on a dead-end street with very little traffic. This is definitely a superhost home, all your condiments, lots of nice touches and snacks/gifts. We will definitely stay there again on our next visit to family in Chicago. House is locate between 41 and 94 making travel around Chicago easy.

Glen Ellyn Home
The property was very nice. It was well maintained and our family with our grandson were very comfortable. If we were to have a negative comment is that the heat distribution was not even throughout the home. The upstairs where the three bedrooms were located was very warm and the kitchen, living room and family were quite chilly. However, this did not impede us having a comfortable stay.

Luxurious South Suburban Villa
My team thanks you for your comfortable home, it is what the crew needs after a day working outside on a large solar field array. Whenever on an extended out of town work trip we like to stay at an Airbnb, a much better value than several rooms at hotels. Your home was roomy & comfortable, we enjoyed our stay and thank you for being a great host.

Hidden GEM OASIS in Chicagoland
The place was located in a nice somewhat secluded location yet close to restaurants in Orland Park . Nico would answer text messages within minutes so you never felt disconnected. Would recommend for families . Pet friendly as well .

No Cleaning Fee - Whole House With Hot Tub
Moiz and his team were extremely responsive and helpful throughout the booking process. The home was clean and spacious enough for our family of 6.

Schaumburg Oasis with a Pool and Hidden Garden
This place is a hidden gem and worth every penny. This place has lots to offer and will instantly make you fall in love with it once you get in. The host is great and responded almost immediately whenever I had a question. Will come back.

Spacious Family Glenwood Estates Home w/ Hot Tub!
It was a wonderful experience staying at evolves home. It was very clean, and spacious enough for all my siblings to be comfortable.
Weekly house rentals

Family Friendly Duplex/9 min from MDW/Free Parking
Johanna made us feel warm and welcome. All amenities are included and work well. Excellent shower. She was very responsive and attentive.

Duplex Home RoscoeVillage/Wrigley Free St Parking
Sharleen’s place is in a great location - close to the train and many great restaurants and shops. It was very clean and was the perfect place for our family to stay.

Private 3BR w/ Backyard | LCP Collection
this was a great place lovely 😍 will book again and who ever reading this should book to

Massive 8bd/3ba Building w/ Two Car Garage!
I loved this place. Perfectly accommodated 14 adults and 3 children. Only thing it could use was at least 2 extra blankets and a sheet pan for baking. Other then that, it was perfect! Walking distance to the bus stop to get to the train stain. Aldi (grocery store) 5 minutes away walking distance.

Wicker Park 6bd/4ba, Steps from Cta, Parking Incl
The location alone makes this home worth booking. Add that there’s ample room for family/friends and it’s a gem in the middle of a great Chicago neighborhood. We were a group of six and loved every minute.

The Avondale Guesthouse
We absolutely loved the place! Great location, price and space! Jed was so kind and responsive, and we absolutely loved the the outdoor space! We would definitely stay again!

The Spa of Downtown Whiting
Great host, jacuzzi was great and clean, kitchen had pots and pans and utensils, all bathrooms and rooms were clean and the beach was a nice walk

Wrigleyville Greystone
Fantastic place in an awesome location. Very walkable part of town and a great spot to easily get to Wrigley Field. Found a number of great bars and restaurants in walking distance during our stay. Would definitely stay here again!
Private house rentals

Sleeps 12 Comfortably in 8 Bedrooms 3 Full Bath
This is the 2nd time this year we rented from Michael. He continued to impress with the responsiveness. This time we filled the whole house, all bedrooms and both floors, 12 in total, mix of kids and adults. We decorated for Christmas, made it feel like we were home for the holidays. We walked all around the neighborhood, got coffee in the morning, fresh bread from a fabulous bakery in Downtown Oak Park and always felt safe and enjoyed the friendly neighborhood. The home and bedrooms were warm when you wanted them warm during the day and cool at night to sleep in. Kitchens were well equipped and all the appliances worked perfectly. The tankless water heater was a blessing when we were all trying to get out for a family event. At one point we realized that we were out of trash bags on Christmas morning. Michael had them there in less than 30 minutes. Over the top responsiveness. Being 10 minutes from the Eisenhower makes this convenient to either Downtown or Oak Brook.

Gorgeous and Luxurious 3 BR Home
This is a great house to stay for a family or two couples. Out of several ABNBs, this one gets the award for most clean. There is a fairly new Italian restaurant, Il Girasole Trattoria, that is walk-able and delicious. You will not be disappointed with your stay.

Big Family Home with 4 King Beds
Great having pool table, wall mounted TV, and games in lower level. Appreciated comfortable beds, ample supply of glasses, bowls, flatware, and plates &, large dining space. Clean home, safe & quiet neighborhood, with easy access to major roads & O'Hare. Host provided clear & simple check in instructions

Grand Victorian Mansion in Austin Area
The accommodation was spacious and very comfortable for our large group of 16. While the floors creak a bit, it wasn’t an issue. Samantha was always quick to address any questions and issues. The gated parking area provided ample space for our cars, which was a great convenience.

Warm and comfortable inviting Suburban home !
Great host, nice peaceful home with old-fashioned feel. We even met some friendly neighbors. Rich always responded promptly to questions & was overall kind & accommodating. We enjoyed the area, including many historical homes, local restaurants (DeMar’s😋) and a beautiful event at the iconic Lyric Theater. Thank you!

The Blue House: Family Retreat
This was a wonderful stay I would recommend the host is very attentive if you are looking for a nice chill space with lots of parking this is your spot

Quiet cul-de-sac with huge fenced in backyard
Great host and awesome outdoor space with plenty to do nearby.

*ENTIRE CITY HOUSE/PARKING - 3 MIN WALK TO TRAIN
This Airbnb was well worth the money. It is right by a train system very convenient. The host had the place very clean and ready to go for us and was very helpful. I would recommend this place to anybody.
Quick stats about house rentals in Chicago
Total rentals
2K properties
Total number of reviews
83K reviews
Family-friendly rentals
1.1K properties are a good fit for families
Pet-friendly rentals
530 properties allow pets
Rentals with a pool
20 properties have a pool
Rentals with dedicated workspaces
1.3K properties have a dedicated workspace
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- Millennium Park
- Wrigley Field
- United Center
- Navy Pier
- Frank Lloyd Wright Home and Studio
- Shedd Aquarium
- The Field Museum
- 875 North Michigan Avenue
- Illinois Beach State Park
- Woodlands Course at Whittaker
- Guaranteed Rate Field
- Skydeck Chicago
- Splash Station
- Olympia Fields Country Club
- Deep River Waterpark
- Four Lakes Alpine Snowsports
- Raging Waves Waterpark
- Odyssey Fun World
- Flossmoor Golf Club
- Bengtson's Pumpkin Farm and Fall Fest
- DuSable Museum of African American History
- The Beverly Country Club
- Frederick C. Robie House
- Museum of Science and Industry
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