
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

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

Gold Coast Home|Rooftop |PoolTable |Parking |Views

3bd/3ba Bronzeville Beauty

The Architectural Haven - 15 min from Chicago!

NEW! 3BR/2.5B Duplex in Noble Sq

Floresitas Oasis, your home in Chicago

Warm and comfortable inviting Suburban home !

Modern Victorian Charm | A+ Location in OP

Beverly House
Private house rentals

Family Friendly Duplex/9 min from MDW/Free Parking

The Modern Muse of Chicago! Close to everything!

Lofty Urban Retreat

Big house in the BEST Location!

jane's house - a boutique flat in west town -2b/1b

Spacious whole apt near shopping and city

Private Suite Quiet Safe OakPark

Luxury Home - Pool Tbl/Bar/Patio
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
- Fitness-friendly rentals Chicago
- Rentals with a cinema Chicago
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- Hotel rentals Chicago
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- Flat rentals Chicago
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- Rentals with an EV charger Chicago
- Private suite rentals Chicago
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- Townhouse rentals Chicago
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- Loft rentals Chicago
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- Ski-in/ski-out rentals Chicago
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- Rentals with pools Chicago
- Villa rentals Chicago
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- Rentals with breakfast Chicago
- Rentals with a firepit Chicago
- Family-friendly rentals Chicago
- Apartment rentals Chicago
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- Rentals with an accessible-height bed Chicago
- Smoking-friendly rentals Chicago
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- Millennium Park
- Wrigley Field
- Navy Pier
- United Center
- Oak Street Beach
- Six Flags Great America
- Humboldt Park
- Shedd Aquarium
- 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
- Illinois Beach State Park
- Brookfield Zoo
- Wicker Park
- Washington Park Zoo
- Raging Waves Waterpark
- The 606
- The Beverly Country Club
- Things to do Chicago
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