
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

Stunning Home in Prime Chicago with Private Pool

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

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

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

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

Downtown Retreat: 2BR, Balcony, Resort Comfort

Loop City Views: 2BR Apt, Near Riverwalk

Stylish Corner 2 Bedroom in the Heart of Chicago |

The Metropolitan Retreat (2BD / 2BA)

The Millennium Manor
Destinations to explore
- Chicago Holiday rentals
- Indianapolis Holiday rentals
- Platteville Holiday rentals
- St. Louis Holiday rentals
- Detroit Holiday rentals
- Columbus Holiday rentals
- Louisville Holiday rentals
- Southern Indiana Holiday rentals
- Cincinnati Holiday rentals
- Milwaukee Holiday rentals
- Wisconsin River Holiday rentals
- Windsor Holiday rentals
- House rentals Downtown Chicago
- Rentals with a firepit Downtown Chicago
- Waterfront rentals Downtown Chicago
- Rentals with a cinema Downtown Chicago
- Rentals with outdoor seating Downtown Chicago
- Rentals with beach access Downtown Chicago
- Rentals with a washing machine and dryer Downtown Chicago
- Pet-friendly rentals Downtown Chicago
- Rentals with lake access Downtown Chicago
- Rentals with an EV charger Downtown Chicago
- Loft rentals Downtown Chicago
- Fitness-friendly rentals Downtown Chicago
- Smoking-friendly rentals Downtown Chicago
- Rentals with breakfast Downtown Chicago
- Flat rentals Downtown Chicago
- Rentals with a sauna Downtown Chicago
- Rentals with a fireplace Downtown Chicago
- Townhouse rentals Downtown Chicago
- Family-friendly rentals Downtown Chicago
- Rentals with a hot tub Downtown Chicago
- Apartment rentals Downtown Chicago
- Rentals with a patio Downtown Chicago
- 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
- Illinois Beach State Park
- Wicker Park
- Garfield Park Conservatory
- Washington Park Zoo
- Brookfield Zoo
- Museum of Science and Industry
- Lincoln Park Zoo
- Willis Tower
- Raging Waves Waterpark
- The 606
- The Beverly Country Club
- Things to do Downtown Chicago
- Tours Downtown Chicago
- Nature and outdoors Downtown Chicago
- Sightseeing Downtown Chicago
- Art and culture Downtown Chicago
- Food and drink Downtown Chicago
- Sports activities Downtown Chicago
- Things to do Cook County
- Sports activities Cook County
- Food and drink Cook County
- Sightseeing Cook County
- Tours Cook County
- Art and culture Cook County
- Things to do Illinois
- Tours Illinois
- Art and culture Illinois
- Sports activities Illinois
- Sightseeing Illinois
- Nature and outdoors Illinois
- Food and drink Illinois
- Things to do United States
- Entertainment United States
- Sports activities United States
- Art and culture United States
- Food and drink United States
- Sightseeing United States
- Wellness United States
- Nature and outdoors United States
- Tours United States