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
4.94 out of 5 average rating, 18 reviewsGlen Ellyn Home
Guest favourite
Home in Schaumburg
4.93 out of 5 average rating, 14 reviewsSchaumburg Woodfield Pool House 4bedroom 2.5bath
Guest favourite
Home in Chicago
4.87 out of 5 average rating, 39 reviewsLuxury Cabin in Lakeview
Guest favourite
Home in Chicago
4.84 out of 5 average rating, 19 reviews2Bed+2Bath PentHouse in South Loop
Home in Riverwoods
Riverwoods Nature Retreat
Home in Skokie
Skokie town home
Condo rentals with a pool
Superhost
Condo in Chicago
4.74 out of 5 average rating, 152 reviewsCentral Downtown Location-Modern 2BR Condo
Guest favourite
Condo in Elk Grove Village
4.95 out of 5 average rating, 57 reviewsJust remodeled apartment close to airport and mall
Superhost
Condo in Downers Grove
4.88 out of 5 average rating, 52 reviewsUpscale, Smoke and Pet Free, Washer Dryer, Balcony
Condo in Chicago
4.8 out of 5 average rating, 20 reviewsLovely condo studio
Condo in Chicago
4.68 out of 5 average rating, 28 reviews1 bedroom in the heart of downtown Chicago.
Guest favourite
Condo in Evanston
4.95 out of 5 average rating, 81 reviews"Bliss of Evanston" 180°view, 2BDR +2Bath Urbanlux
Guest favourite
Condo in Evanston
4.94 out of 5 average rating, 72 reviews"Joy of Evanston" 1BDR, KING EXEC Suite, pool+Gym
Guest favourite
Condo in Evanston
4.97 out of 5 average rating, 76 reviews"Unity of Evanston" 3 BDR+2BA ModernLuxe +pool
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