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.
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
Home in Glen Ellyn
4.94 out of 5 average rating, 16 reviewsGlen Ellyn Home
Jul 23 – 30
Home in Schaumburg
4.93 out of 5 average rating, 14 reviewsSchaumburg Woodfield Pool House 4bedroom 2.5bath
Aug 17 – 24
Home in Chicago
4.86 out of 5 average rating, 37 reviewsLuxury Cabin in Lakeview
Jul 7 – 14
Home in Chicago
4.8 out of 5 average rating, 15 reviews2Bed+2Bath PentHouse in South Loop
Feb 2 – 9
Home in Lisle
Cozy Lisle Home w/ Fenced Backyard: Pets Welcome!
Jul 26 – Aug 2
Home in Riverwoods
Riverwoods Nature Retreat
May 5 – 12
Home in Lisle
Welcoming, cozy, and a fur baby paradise.
Sep 27 – Oct 4
Home in Skokie
Skokie town home
Aug 6 – 13
Condo rentals with a pool
Condo in Chicago
4.75 out of 5 average rating, 145 reviewsCentral Downtown Location-Modern 2BR Condo
Jul 21 – 28
Condo in Elk Grove Village
4.95 out of 5 average rating, 56 reviewsJust remodeled apartment close to airport and mall
Oct 26 – Nov 2
Condo in Lombard
4.97 out of 5 average rating, 36 reviewsPond View, Washer Dryer, Non Smoking, Pet Free
Oct 2 – 9
Condo in Chicago
4.75 out of 5 average rating, 16 reviewsLovely condo studio
Nov 3 – 10
Condo in Chicago
4.7 out of 5 average rating, 27 reviews1 bedroom in the heart of downtown Chicago.
Jul 21 – 28
Condo in Evanston
4.94 out of 5 average rating, 71 reviews"Joy of Evanston" 1BDR, KING EXEC Suite, pool+Gym
Jul 24 – 31
Condo in Evanston
4.95 out of 5 average rating, 79 reviews"Bliss of Evanston" 180°view, 2BDR +2Bath Urbanlux
Dec 19 – 26
Condo in Evanston
4.97 out of 5 average rating, 73 reviews"Unity of Evanston" 3 BDR+2BA ModernLuxe +pool
Oct 21 – 28
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