
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 Chicago
5 out of 5 average rating, 6 reviewsLuxury Condo Downtown Chicago

Home in Lockport
4.67 out of 5 average rating, 3 reviewsHidden GEM OASIS in Chicagoland
Guest favourite

Home in Schaumburg
4.87 out of 5 average rating, 15 reviewsSchaumburg Oasis with a Pool and Hidden Garden
Guest favourite

Home in Carol Stream
4.86 out of 5 average rating, 7 reviewsSpacious 4 Bed/3.5 Bath Sleeps 8+
Apartment rentals with a pool
Guest favourite

Apartment in Downers Grove
4.92 out of 5 average rating, 61 reviewsUpscale, Washer Dryer, Smoke Free, Pet Free,
Guest favourite

Apartment in Evanston
4.95 out of 5 average rating, 87 reviews"Joy of Evanston" 1BDR, KING EXEC Suite, pool+Gym
Guest favourite

Apartment in Evanston
4.96 out of 5 average rating, 98 reviews"Bliss of Evanston" 180°view, 2BDR +2Bath Urbanlux

Apartment in Chicago
New place to stayvoco: Balcony & City View
Guest favourite

Apartment in Elk Grove Village
4.95 out of 5 average rating, 78 reviewsJust remodeled apartment close to airport and mall
Guest favourite

Apartment in Evanston
4.91 out of 5 average rating, 119 reviewsChicago's Treasure "Heart of Evanston" 2bdr +1 Ba

Apartment in Lombard
4.91 out of 5 average rating, 45 reviewsPond View, Washer Dryer, Non Smoking Community
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