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Vacation rentals with a pool in Chicago
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Chicago
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Chicago rentals with a pool
House rentals with a pool
![](https://a0.muscache.com/im/pictures/hosting/Hosting-868236911692412929/original/860125fb-662e-4cc7-ba73-7bf9a86831a2.jpeg?im_w=720)
Home in Schaumburg
4.94 out of 5 average rating, 16 reviewsSchaumburg Woodfield Pool House 4bedroom 2.5bath
![](https://a0.muscache.com/im/pictures/69d3bb7c-54f2-4454-ae3a-c4d38c5c61fe.jpg?im_w=720)
Home in Schaumburg
4.9 out of 5 average rating, 10 reviewsParadise 4BR w/ Pool & Games
![](https://a0.muscache.com/im/pictures/miso/Hosting-782525235032023073/original/c259bfd1-4e3a-4829-bd35-243c8b9b3f53.jpeg?im_w=720)
Home in Lincoln Park
4.84 out of 5 average rating, 44 reviewsLuxury Cabin in Lakeview
![](https://a0.muscache.com/im/pictures/hosting/Hosting-983449221511856312/original/2798be2f-5303-40c1-9ad5-61801e5cbee2.jpeg?im_w=720)
Home in Chicago Heights
4.33 out of 5 average rating, 3 reviewsOlympia field -matteson IL- homewood, park forest
![](https://a0.muscache.com/im/pictures/miso/Hosting-712645297244516225/original/508f7851-9be2-4817-82b1-9f284fe1dee4.jpeg?im_w=720)
Home in New Lenox
4.76 out of 5 average rating, 38 reviewsCheerful home. Heated pool, Hot tub!
![](https://a0.muscache.com/im/pictures/6e90a0bd-6fa5-4c48-abeb-6f53d9433c9e.jpg?im_w=720)
Home in Near South Side
4.81 out of 5 average rating, 21 reviews2Bed+2Bath PentHouse in South Loop
![](https://a0.muscache.com/im/pictures/hosting/Hosting-994838543044727938/original/b92bba1e-28c3-424a-b304-c7e238f1c6d5.jpeg?im_w=720)
Home in Schererville
4.92 out of 5 average rating, 12 reviewsCozy house in Schererville
![](https://a0.muscache.com/im/pictures/083b0f7b-389d-46c3-9bbd-9a87a7e04d10.jpg?im_w=720)
Home in Plainfield
4.9 out of 5 average rating, 30 reviewsPool* 3 King beds* Grill & Patio* 30mi to Chicago
Condo rentals with a pool
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Condo in The Loop
4.74 out of 5 average rating, 156 reviewsCentral Downtown Location-Modern 2BR Condo
![](https://a0.muscache.com/im/pictures/f669ed83-53c2-463d-91ad-ce37cb3e51c5.jpg?im_w=720)
Condo in Lombard
4.85 out of 5 average rating, 47 reviewsSmoke & Pet Free, Washer Dryer, Fireplace, Balcony
![](https://a0.muscache.com/im/pictures/3a6afd47-9f00-4a17-b390-b3961c529a06.jpg?im_w=720)
Condo in Uptown
4.71 out of 5 average rating, 21 reviewsLovely condo studio
![](https://a0.muscache.com/im/pictures/b82136a8-fc12-4601-a319-ce1905a52d32.jpg?im_w=720)
Condo in Near North Side
4.7 out of 5 average rating, 30 reviews1 bedroom in the heart of downtown Chicago.
![](https://a0.muscache.com/im/pictures/miso/Hosting-557105766619361899/original/29ed47bb-f3f2-4026-8c52-dc242a910254.jpeg?im_w=720)
Condo in Evanston
4.95 out of 5 average rating, 82 reviews"Bliss of Evanston" 180°view, 2BDR +2Bath Urbanlux
![](https://a0.muscache.com/im/pictures/miso/Hosting-557066289155135782/original/1c4279af-636f-4d76-a613-da35f04ec05e.jpeg?im_w=720)
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-557121615351527525/original/a1f25861-e370-46e3-8b57-4beeef1a0bf4.jpeg?im_w=720)
Condo in Evanston
4.97 out of 5 average rating, 78 reviews"Unity of Evanston" 3 BDR+2BA ModernLuxe +pool
![](https://a0.muscache.com/im/pictures/797d8d64-5ef4-4588-a00c-8ead6a4b9e87.jpg?im_w=720)
Condo in Lombard
4.95 out of 5 average rating, 39 reviewsPond View, Washer Dryer, Non Smoking, Pet Free
Quick stats about vacation rentals with a pool in Chicago
Total rentals
1.1K properties
Total number of reviews
9.2K reviews
Family-friendly rentals
300 properties are a good fit for families
Pet-friendly rentals
700 properties allow pets
Rentals with dedicated workspaces
740 properties have a dedicated workspace
Wifi availability
1.1K properties include access to wifi
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