
House holiday rentals in Chicago
Find and book unique houses on Airbnb
Top-rated house rentals in Chicago
Guests agree: These houses are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Chicago house rentals
House rentals with a pool

Pardizes Suites

Glen Ellyn Home

Munster hide away

Hidden GEM OASIS in Chicagoland with inground POOL

Rosemont 4BD2BA house with Pool

Now Open: Heated Pool with Entire House

Luxury fenced in modern ranch

Spacious Family Glenwood Estates Home w/ Hot Tub!
Weekly house rentals

The Modern Muse of Chicago! Close to everything!

The Architectural Haven - 15 min from Chicago!

Duplex Home RoscoeVillage/Wrigley Free St Parking

The Roscoe House near Wrigley Field

Home in Glen Ellyn

BoHo House - A Chic, 1903 Chicago Workers Cottage

Wrigleyville Southport Studio

Big house in the BEST Location!
Private house rentals

Casa 22 | Luxury Modern House for 6 | 3 Bed,2 Bath

Charming 3bd Bungalow In Vibrant Andersonville

Luxury-Near Downtown & United Center-Sleeps 14

WrigleyRoost <5 min to Cubs/train/lake!

Beverly House

Luxe Spa Sleeps 16 Rooftop Garage 18mins to Center

The Black HOUSE! In the Historic Chatham Area.

Wicker Park Entire House, Private Yard and Parking
Quick stats about house rentals in Chicago
Total rentals
1.9K properties
Total number of reviews
86K reviews
Family-friendly rentals
1.1K properties are a good fit for families
Pet-friendly rentals
520 properties allow pets
Rentals with a pool
10 properties have a pool
Rentals with dedicated workspaces
1.3K properties have a dedicated workspace
Destinations to explore
- Downtown Chicago Holiday rentals
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- West Side Holiday rentals
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- Lake Michigan Beach Holiday rentals
- Evanston Holiday rentals
- Rentals with a home theatre Chicago
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- Millennium Park
- Wrigley Field
- United Center
- Navy Pier
- Six Flags Great America
- Oak Street Beach
- Humboldt Park
- Shedd Aquarium
- Frank Lloyd Wright Home and Studio
- Guaranteed Rate Field
- 875 North Michigan Avenue
- The Field Museum
- Lincoln Park
- Washington Park Zoo
- Brookfield Zoo
- Museum of Science and Industry
- Illinois Beach State Park
- Garfield Park Conservatory
- Wicker Park
- Lincoln Park Zoo
- Willis Tower
- Raging Waves Waterpark
- The 606
- The Beverly Country Club
- Things to do Chicago
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