
House holiday rentals in Downtown Chicago
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Top-rated house rentals in Downtown 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 Downtown Chicago
House rentals with a pool

Pardizes Suites

Glen Ellyn Home

Rosemont 4BD2BA house with Pool

Now Open: Heated Pool with Entire House

Riverwoods Nature Retreat

Celebrate at Hacjenda house

Luxury Loft with Private Pool and Movie Theater

Paradise with Pool & Games
Weekly house rentals

The Modern Muse of Chicago! Close to everything!

3bd/3ba Bronzeville Beauty

NEW! 3BR/2.5B Duplex in Noble Sq

Gorgeous and Luxurious 3 BR Home

3 bd/ 2ba with Free Parking Spot by McCormick

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

Private Downtown Retreat with Rooftop Oasis

Modern SFH Near McCormick Place & Soldier Field
Private house rentals

CasaNova Modern City Living

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

Sunny Historic Cottage on the Park

Big house in the BEST Location!

Executive Contemporary Duplex

Villa Noir Chicago Victorian 7 min to downtown

Smart Home King Bed Private Yard

Lakeview Condo
Destinations to explore
- Milwaukee Holiday rentals
- Lake Geneva Holiday rentals
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- Apartment rentals Downtown Chicago
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- Millennium Park
- Wrigley Field
- Navy Pier
- United Center
- Oak Street Beach
- Humboldt Park
- Six Flags Great America
- Shedd Aquarium
- Guaranteed Rate Field
- 875 North Michigan Avenue
- The Field Museum
- Lincoln Park
- Frank Lloyd Wright Home and Studio
- Garfield Park Conservatory
- Museum of Science and Industry
- Lincoln Park Zoo
- Willis Tower
- Illinois Beach State Park
- Brookfield Zoo
- Wicker Park
- Washington Park Zoo
- Raging Waves Waterpark
- The 606
- The Beverly Country Club
- Things to do Downtown Chicago
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