House vacation rentals in Chicago

Find and book unique houses on Airbnb

0 of 0 items showing
1 of 3 pages

Popular amenities for Chicago house rentals

House rentals with a pool

Guest favourite
Home in Highland Park
4.92 out of 5 average rating, 142 reviews

2-Acre Highland Park Retreat with Heated Pool ~ 5*

JeffRating, 5 stars3 months ago
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.
Guest favourite
Home in Glen Ellyn
4.95 out of 5 average rating, 20 reviews

Glen Ellyn Home

TimothyRating, 5 stars3 months ago
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.
Home in Olympia Fields
4.56 out of 5 average rating, 43 reviews

Luxurious South Suburban Villa

LanceRating, 5 stars1 month ago
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.
Home in Lockport
4.8 out of 5 average rating, 5 reviews

Hidden GEM OASIS in Chicagoland

RichardRating, 5 stars1 week ago
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 .
Top guest favourite
Home in Bloomingdale
4.93 out of 5 average rating, 45 reviews

No Cleaning Fee - Whole House With Hot Tub

NafisahRating, 5 stars2 days ago
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.
Guest favourite
Home in Schaumburg
4.9 out of 5 average rating, 20 reviews

Schaumburg Oasis with a Pool and Hidden Garden

Arun KumarRating, 5 stars1 week ago
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.
Home in Glenwood
4.8 out of 5 average rating, 55 reviews

Spacious Family Glenwood Estates Home w/ Hot Tub!

JosiahRating, 5 stars4 months ago
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

Superhost
Home in West Lawn
4.94 out of 5 average rating, 36 reviews

Family Friendly Duplex/9 min from MDW/Free Parking

AshleyRating, 5 stars1 week ago
Johanna made us feel warm and welcome. All amenities are included and work well. Excellent shower. She was very responsive and attentive.
Guest favourite
Home in Roscoe Village
4.92 out of 5 average rating, 275 reviews

Duplex Home RoscoeVillage/Wrigley Free St Parking

EmilyRating, 5 stars6 days ago
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.
Superhost
Home in Bolingbrook
4.73 out of 5 average rating, 22 reviews

Private 3BR w/ Backyard | LCP Collection

CarltonRating, 5 stars8 months ago
this was a great place lovely 😍 will book again and who ever reading this should book to
Superhost
Home in Humboldt Park
4.88 out of 5 average rating, 8 reviews

Massive 8bd/3ba Building w/ Two Car Garage!

SonyaRating, 5 stars1 month ago
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.
Top guest favourite
Home in Wicker Park
4.97 out of 5 average rating, 32 reviews

Wicker Park 6bd/4ba, Steps from Cta, Parking Incl

LaureenRating, 5 stars1 week ago
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.
Guest favourite
Home in Avondale
4.86 out of 5 average rating, 221 reviews

The Avondale Guesthouse

ErickaRating, 5 stars5 months ago
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!
Superhost
Home in Whiting
4.84 out of 5 average rating, 149 reviews

The Spa of Downtown Whiting

DonRating, 5 stars1 week ago
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
Top guest favourite
Home in Lake View
4.95 out of 5 average rating, 183 reviews

Wrigleyville Greystone

ThomasRating, 5 stars4 days ago
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

Superhost
Home in Oak Park
5 out of 5 average rating, 4 reviews

Sleeps 12 Comfortably in 8 Bedrooms 3 Full Bath

VinceRating, 5 stars2 months ago
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.
Guest favourite
Home in Logan Square
4.95 out of 5 average rating, 39 reviews

Gorgeous and Luxurious 3 BR Home

SeanRating, 5 stars5 months ago
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.
Top guest favourite
Home in Elmhurst
5 out of 5 average rating, 43 reviews

Big Family Home with 4 King Beds

LynnRating, 5 stars4 days ago
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
Superhost
Home in Austin
4.88 out of 5 average rating, 48 reviews

Grand Victorian Mansion in Austin Area

SaifRating, 5 stars5 months ago
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.
Superhost
Home in Blue Island
4.81 out of 5 average rating, 190 reviews

Warm and comfortable inviting Suburban home !

LuCindaRating, 5 stars1 month ago
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!
Superhost
Home in Gary
4.87 out of 5 average rating, 39 reviews

The Blue House: Family Retreat

JacquelineRating, 5 stars1 week ago
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
Top guest favourite
Home in Chicago Ridge
4.93 out of 5 average rating, 120 reviews

Quiet cul-de-sac with huge fenced in backyard

JoelRating, 5 stars1 week ago
Great host and awesome outdoor space with plenty to do nearby.
Superhost
Home in Near West Side
4.84 out of 5 average rating, 496 reviews

*ENTIRE CITY HOUSE/PARKING - 3 MIN WALK TO TRAIN

JamesRating, 5 stars5 days ago
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

Destinations to explore

  1. Airbnb
  2. United States
  3. Illinois
  4. Cook County
  5. Chicago
  6. House rentals