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Vacation 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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Vacation 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
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Guest favorite
Home in Glen Ellyn
4.94 out of 5 average rating, 18 reviewsGlen Ellyn Home
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Guest favorite
Home in Schaumburg
4.93 out of 5 average rating, 14 reviewsSchaumburg Woodfield Pool House 4bedroom 2.5bath
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Guest favorite
Home in Chicago
4.87 out of 5 average rating, 39 reviewsLuxury Cabin in Lakeview
![](https://a0.muscache.com/im/pictures/6e90a0bd-6fa5-4c48-abeb-6f53d9433c9e.jpg?im_w=720)
Guest favorite
Home in Chicago
4.84 out of 5 average rating, 19 reviews2Bed+2Bath PentHouse in South Loop
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Home in Riverwoods
Riverwoods Nature Retreat
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Home in Skokie
Skokie town home
Condo rentals with a pool
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Superhost
Condo in Chicago
4.74 out of 5 average rating, 152 reviewsCentral Downtown Location-Modern 2BR Condo
![](https://a0.muscache.com/im/pictures/miso/Hosting-666950257559901732/original/c0078b72-7a30-43d5-84fd-8c7bcf711ea4.jpeg?im_w=720)
Guest favorite
Condo in Elk Grove Village
4.95 out of 5 average rating, 57 reviewsJust remodeled apartment close to airport and mall
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Superhost
Condo in Downers Grove
4.88 out of 5 average rating, 52 reviewsUpscale, Smoke and Pet Free, Washer Dryer, Balcony
![](https://a0.muscache.com/im/pictures/3a6afd47-9f00-4a17-b390-b3961c529a06.jpg?im_w=720)
Condo in Chicago
4.8 out of 5 average rating, 20 reviewsLovely condo studio
![](https://a0.muscache.com/im/pictures/b82136a8-fc12-4601-a319-ce1905a52d32.jpg?im_w=720)
Condo in Chicago
4.68 out of 5 average rating, 28 reviews1 bedroom in the heart of downtown Chicago.
![](https://a0.muscache.com/im/pictures/miso/Hosting-557066289155135782/original/1c4279af-636f-4d76-a613-da35f04ec05e.jpeg?im_w=720)
Guest favorite
Condo in Evanston
4.94 out of 5 average rating, 72 reviews"Joy of Evanston" 1BDR, KING EXEC Suite, pool+Gym
![](https://a0.muscache.com/im/pictures/miso/Hosting-557105766619361899/original/29ed47bb-f3f2-4026-8c52-dc242a910254.jpeg?im_w=720)
Guest favorite
Condo in Evanston
4.95 out of 5 average rating, 81 reviews"Bliss of Evanston" 180°view, 2BDR +2Bath Urbanlux
![](https://a0.muscache.com/im/pictures/miso/Hosting-557121615351527525/original/a1f25861-e370-46e3-8b57-4beeef1a0bf4.jpeg?im_w=720)
Guest favorite
Condo in Evanston
4.97 out of 5 average rating, 76 reviews"Unity of Evanston" 3 BDR+2BA ModernLuxe +pool
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