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.
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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
Guest favourite
Home in Glen Ellyn
Glen Ellyn Home
Guest favourite
Home in Schaumburg
Schaumburg Woodfield Pool House 4bedroom 2.5bath
Guest favourite
Home in Chicago
Luxury Cabin in Lakeview
Guest favourite
Home in Chicago
2Bed+2Bath PentHouse in South Loop
Home in Riverwoods
Riverwoods Nature Retreat
Home in Skokie
Skokie town home
Apartment rentals with a pool
Superhost
Apartment in Chicago
Central Downtown Location-Modern 2BR Condo
Guest favourite
Apartment in Elk Grove Village
Just remodeled apartment close to airport and mall
Guest favourite
Apartment in Lombard
Pond View, Washer Dryer, Non Smoking, Pet Free
Apartment in Chicago
Lovely condo studio
Apartment in Chicago
1 bedroom in the heart of downtown Chicago.
Guest favourite
Apartment in Evanston
"Bliss of Evanston" 180°view, 2BDR +2Bath Urbanlux
Guest favourite
Apartment in Evanston
"Joy of Evanston" 1BDR, KING EXEC Suite, pool+Gym
Guest favourite
Apartment in Lombard
Smoke & Pet Free, Washer Dryer, Fireplace, Balcony
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