
Holiday rentals with a pool in Downtown Chicago
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Downtown Chicago
Guests agree: these homes with a pool 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 Downtown Chicago rentals with a pool
House rentals with a pool

2BR w/ Stunning Views and Resort-Style Amenities

Luxury fenced in modern ranch

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

Rosemont 4BD2BA house with Pool

Lucky #7 w/ pool & gym

Schaumburg Woodfield Pool House 4bedroom 2.5bath

Downtown 2BR: Unique Amenities, Ideal for Tourism

Luxury Loft with Private Pool and Movie Theater
Apartment rentals with a pool

"Joy of Evanston" 1BDR, KING EXEC Suite, pool+Gym

Smoke & Pet Free, Washer Dryer, Fireplace, Balcony

Just remodeled apartment close to airport and mall

Chicago's Treasure "Heart of Evanston" 2bdr +1 Ba

Pond View, Washer Dryer, Non Smoking Community

"Unity of Evanston" 3 BDR+2BA ModernLuxe +pool

Iconic Style, Charming Lake View

Upscale, Smoke and Pet Free, Washer Dryer, Balcony
Other holiday rentals with a pool

River North 2BR: Balcony, Walk to Mag Mile, Pool

Top-Notch 2BR: The Bean View, Loop, Balcony

"Serenity of Evanston" 2 BDR/2Bath Modern Suite

Loop City Views: 2BR Apt, Near Riverwalk

West Loop PH: Fireplace Deck, Incredible Views

Sky-High Living: Lake Views, Elite Experience

The Parkside Pavilion

Fulton Mkt Stylish 3BR w/ Balcony & Top Amenities
Destinations to explore
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- Townhouse rentals Downtown Chicago
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- Rentals with lake access Downtown Chicago
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- Rentals with a washing machine and dryer Downtown Chicago
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- Rentals with pools Cook County
- Rentals with pools Illinois
- Rentals with pools United States
- Lincoln Park
- Millennium Park
- Wrigley Field
- United Center
- Navy Pier
- Six Flags Great America
- Shedd Aquarium
- Humboldt Park
- Guaranteed Rate Field
- 875 North Michigan Avenue
- Frank Lloyd Wright Home and Studio
- Oak Street Beach
- The Field Museum
- Wicker Park
- Lincoln Park Zoo
- Garfield Park Conservatory
- Illinois Beach State Park
- Washington Park Zoo
- Museum of Science and Industry
- Brookfield Zoo
- Willis Tower
- Raging Waves Waterpark
- The Beverly Country Club
- The 606
- Things to do Downtown Chicago
- Sightseeing Downtown Chicago
- Nature and outdoors Downtown Chicago
- Art and culture Downtown Chicago
- Tours Downtown Chicago
- Food and drink Downtown Chicago
- Sports activities Downtown Chicago
- Things to do Cook County
- Sports activities Cook County
- Art and culture Cook County
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- Sightseeing Cook County
- Nature and outdoors Cook County
- Food and drink Cook County
- Things to do Illinois
- Tours Illinois
- Food and drink Illinois
- Sightseeing Illinois
- Sports activities Illinois
- Art and culture Illinois
- Nature and outdoors Illinois
- Things to do United States
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