Condo vacation rentals in Downtown Chicago
Find and book unique condos on Airbnb
Top-rated condo rentals in Downtown Chicago
Guests agree: these condos 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 condo rentals
Weekly condo rentals
Condo in Chicago
4.8 out of 5 average rating, 123 reviewsSpacious Home, Incredible Lakeview Location
Condo in Chicago
4.92 out of 5 average rating, 255 reviewsModern/Spacious 2BR/2BA West Town
Condo in Chicago
4.92 out of 5 average rating, 131 reviewsModern designed 2bed/2bath | Heart of Bronzeville!
Condo in Chicago
4.79 out of 5 average rating, 226 reviewsDowntown Urban Oasis 3BR + Huge Deck & Parking!
Condo in Chicago
4.96 out of 5 average rating, 467 reviewsUnique Lincoln Park Duplex Apt
Condo in Chicago
4.98 out of 5 average rating, 227 reviewsPets OK | Walk Score 95 | Desk | 1,750ft² |W/D
Condo in Chicago
4.74 out of 5 average rating, 284 reviewsChic Home! Walk to Nightlife-Comedy-Restaurants!
Condo in Chicago
4.74 out of 5 average rating, 125 reviewsCabin 103 at 747 Lofts
Pet-friendly condo rentals
Condo in Des Plaines
4.84 out of 5 average rating, 45 reviews2 BD Queen Suite 1 min from Allstate Arena/Malls
Condo in Chicago
4.86 out of 5 average rating, 116 reviews816 PiLZeN Luxury | Rooftop | Garage Parking
Condo in Chicago
4.89 out of 5 average rating, 257 reviews2 King Bed Condo Easy Downtown Free Street Parking
Condo in Chicago
4.97 out of 5 average rating, 373 reviewsLincoln Square Gem!
Condo in Chicago
4.84 out of 5 average rating, 117 reviewsDowntown Mich Ave #7|Safe Park 2bd Penthouse|+gym
Condo in Chicago
4.93 out of 5 average rating, 215 reviewsPvt 1bdr Rogers Park, Loyola, Northwestern.
Condo in Chicago
4.91 out of 5 average rating, 324 reviewsSusie's Space. 2BR easy parking & pet friendly
Condo in Chicago
4.81 out of 5 average rating, 102 reviewsVintage West Town Charmer; Steps to Grand Ave Bus
Condo rentals with a pool
Condo in Oak Lawn
5 out of 5 average rating, 3 reviews2flr Big-3bedrms 2bath with Garage Parking
Condo in Evanston
4.95 out of 5 average rating, 83 reviews"Joy of Evanston" 1BDR, KING EXEC Suite, pool+Gym
Condo in Evanston
4.96 out of 5 average rating, 91 reviews"Bliss of Evanston" 180°view, 2BDR +2Bath Urbanlux
Condo in Oak Lawn
5 out of 5 average rating, 7 reviews1flr Spacious-3Bedrooms/2 Bath w Garage Parking
Condo in Elk Grove Village
4.94 out of 5 average rating, 71 reviewsJust remodeled apartment close to airport and mall
Condo in Chicago
4.8 out of 5 average rating, 25 reviewsLovely condo studio
Condo in Evanston
4.91 out of 5 average rating, 117 reviewsChicago's Treasure "Heart of Evanston" 2bdr +1 Ba
Condo in Evanston
4.96 out of 5 average rating, 89 reviews"Unity of Evanston" 3 BDR+2BA ModernLuxe +pool
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