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

Chic Fulton Market Oasis + Curated Comfort & Style

Luxury fenced in modern ranch

Elmhurst Luxury 4BR w/ Pool, Fenced Yard, Downtown

Rosemont 4BD2BA house with Pool

Lucky #7 w/ Gym

Schaumburg Woodfield Pool House 4bedroom 2.5bath

Luxury Loft with Private Pool and Movie Theater
Weekly house rentals

The Modern Muse of Chicago! Close to everything!

Gold Coast Home|Rooftop |PoolTable |Parking |Views

City Cottage in Logan Square-Avondale

NEW! 3BR/2.5B Duplex in Noble Sq

Vibrant, Spacious Chinatown Home

Private Downtown Retreat with Rooftop Oasis

Windy City White House (3br/2ba) *New Listing*

4 BR • Theater Room • Gym • Walk to Lincoln Park!
Private house rentals

3bd/3ba Bronzeville Beauty

The Architectural Haven

Old Town Cosmopolitan Four Bedroom, Four Bath

Amazing 4BR/4BA Oasis w/ Rooftop & Stunning Design

CasaNova Modern City Living

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

WrigleyRoost <5 min to Cubs/train/lake!

Executive Contemporary Duplex
Destinations to explore
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- Smoking-friendly rentals Downtown Chicago
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- Apartment rentals Downtown Chicago
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- Waterfront rentals Downtown Chicago
- House rentals Cook County
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- Lincoln Park
- Wrigley Field
- Millennium Park
- United Center
- Navy Pier
- Six Flags Great America
- Shedd Aquarium
- 875 North Michigan Avenue
- Humboldt Park
- Guaranteed Rate Field
- Frank Lloyd Wright Home and Studio
- Oak Street Beach
- The Field Museum
- Wicker Park
- Garfield Park Conservatory
- Lincoln Park Zoo
- Museum of Science and Industry
- Brookfield Zoo
- Illinois Beach State Park
- Washington Park Zoo
- Willis Tower
- The Beverly Country Club
- Raging Waves Waterpark
- The 606
- Things to do Downtown Chicago
- Food and drink Downtown Chicago
- Art and culture Downtown Chicago
- Nature and outdoors Downtown Chicago
- Sports activities Downtown Chicago
- Sightseeing Downtown Chicago
- Tours Downtown Chicago
- Things to do Cook County
- Sports activities Cook County
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- Nature and outdoors Cook County
- Entertainment Cook County
- Sightseeing Cook County
- Food and drink Cook County
- Art and culture Cook County
- Things to do Illinois
- Art and culture Illinois
- Tours Illinois
- Sightseeing Illinois
- Sports activities Illinois
- Food and drink Illinois
- Nature and outdoors Illinois
- Things to do United States
- Tours United States
- Nature and outdoors United States
- Food and drink United States
- Sightseeing United States
- Wellness United States
- Entertainment United States
- Art and culture United States
- Sports activities United States