
House holiday rentals in Chicago
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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 house rentals in Chicago
House rentals with a pool

Pardizes Suites

Munster hide away

Rosemont 4BD2BA house with Pool

Now Open: Heated Pool with Entire House

Schaumburg Oasis:Private Pool & Enchanted Garden

Luxury Loft with Private Pool and Movie Theater

Luxury fenced in modern ranch

Stunning Home in Prime Chicago with Private Pool
Weekly house rentals

The Modern Muse of Chicago! Close to everything!

Gold Coast Home|Rooftop |PoolTable |Parking |Views

3bd/3ba Bronzeville Beauty

3BD Home Mins from Airport | Free Wi-Fi + Parking

Modern & Private Basement Retreat with Kitchenette

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

Sunny Historic Cottage on the Park

Wrigleyville Southport Studio
Private house rentals

NEW! 3BR/2.5B Duplex in Noble Sq

1mi to Beach | 2-Floor Loft | Foosball

Gorgeous and Luxurious 3 BR Home

Big house in the BEST Location!

Oak Park - Wine House!

Beverly House

Lakeview Condo

① Luxe | Spa | Rooftop | Modern | 4 Mi to Downtown
Quick stats about house rentals in Chicago
Total rentals
2K properties
Total number of reviews
84K reviews
Family-friendly rentals
1.1K properties are a good fit for families
Pet-friendly rentals
520 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
- Downtown Chicago Holiday rentals
- Milwaukee Holiday rentals
- Lake Geneva Holiday rentals
- West Side Holiday rentals
- North Side Holiday rentals
- South Bend Holiday rentals
- South Haven Holiday rentals
- Holland Holiday rentals
- Saugatuck Holiday rentals
- South Side Holiday rentals
- Lake Michigan Beach Holiday rentals
- Evanston Holiday rentals
- Rentals with beach access Chicago
- Rentals with an accessible-height bed Chicago
- Smoking-friendly rentals Chicago
- Fitness-friendly rentals Chicago
- Rentals with an EV charger Chicago
- Lakehouse rentals Chicago
- Rentals with lake access Chicago
- Rentals with a cinema Chicago
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- Rentals with a balcony Chicago
- Flat rentals Chicago
- Beachfront rentals Chicago
- Rentals with pools Chicago
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- Apartment rentals Chicago
- Rentals with a hot tub Chicago
- Loft rentals Chicago
- Hotel rentals Chicago
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- Rentals with breakfast Chicago
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- Rentals with a washing machine and dryer Chicago
- Bed and breakfasts Chicago
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- Millennium Park
- Wrigley Field
- Navy Pier
- United Center
- Oak Street Beach
- Shedd Aquarium
- Humboldt Park
- Six Flags Great America
- Guaranteed Rate Field
- 875 North Michigan Avenue
- The Field Museum
- Lincoln Park
- Frank Lloyd Wright Home and Studio
- Museum of Science and Industry
- Garfield Park Conservatory
- Willis Tower
- Lincoln Park Zoo
- Brookfield Zoo
- Illinois Beach State Park
- Wicker Park
- Washington Park Zoo
- The 606
- Raging Waves Waterpark
- Flossmoor Golf Club
- Things to do Chicago
- Food and drink Chicago
- Tours Chicago
- Sightseeing Chicago
- Art and culture Chicago
- Nature and outdoors Chicago
- Things to do Cook County
- Food and drink Cook County
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- Art and culture Cook County
- Things to do Illinois
- Sightseeing Illinois
- Art and culture Illinois
- Nature and outdoors Illinois
- Food and drink Illinois
- Tours Illinois
- Things to do United States
- Sightseeing United States
- Food and drink United States
- Wellness United States
- Nature and outdoors United States
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- Tours United States
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- Entertainment United States