
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

Luxury fenced in modern ranch

Rosemont 4BD2BA house with Pool

LUXURY - Movie Theater + Spa House

Lucky #7 w/ pool & gym

Schaumburg Woodfield Pool House 4bedroom 2.5bath

Celebrate at Hacjenda house
Weekly house rentals

The Modern Muse of Chicago! Close to everything!

The Architectural Haven

Private 3rd Floor Apartment

Big house in the BEST Location!

Opulent 3bdr2bth Old Town Luxury + Parking prmts

Mid-Century Gem By United Center: Hot Tub & Sauna

Modern SFH Near McCormick Place & Soldier Field

The Black HOUSE! In the Historic Chatham Area.
Private house rentals

CasaNova Modern City Living

Experience Chicago from Our 3-Story Retreat

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

Vibrant, Spacious Chinatown Home

Private Downtown Retreat with Rooftop Oasis

Executive Contemporary Duplex

Luxe Spa Sleeps 16 Rooftop Garage 18mins to Center

Andersonville Home for Groups! Hot Tub Yard Garage
Destinations to explore
- Milwaukee Holiday rentals
- Lake Geneva Holiday rentals
- West Side Holiday rentals
- North Side Holiday rentals
- South Bend Holiday rentals
- South Haven Holiday rentals
- Saugatuck Holiday rentals
- Holland Holiday rentals
- South Side Holiday rentals
- Lake Michigan Beach Holiday rentals
- Evanston Holiday rentals
- Chicago Holiday rentals
- Family-friendly rentals Downtown Chicago
- Rentals with breakfast Downtown Chicago
- Apartment rentals Downtown Chicago
- Rentals with a hot tub Downtown Chicago
- Rentals with an EV charger Downtown Chicago
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- Waterfront rentals Downtown Chicago
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- Rentals with a washing machine and dryer Downtown Chicago
- Townhouse rentals Downtown Chicago
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- Rentals with beach access Downtown Chicago
- Rentals with a cinema Downtown Chicago
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- Hotel rentals Downtown 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
- Willis Tower
- Lincoln Park Zoo
- Raging Waves Waterpark
- The 606
- The Beverly Country Club
- Things to do Downtown Chicago
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