Condo vacation rentals in Downtown Chicago
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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
4.9 out of 5 average rating, 140 reviewsEast Garfield Park 2 Bedroom
Condo in Chicago
4.96 out of 5 average rating, 112 reviewsCHIC DOWNTOWN PENTHOUSE w/ private roof +parking
Condo in Chicago
4.97 out of 5 average rating, 124 reviewsWrigleyville Inn. Historic Greystone. Parking pass
Condo in Chicago
4.92 out of 5 average rating, 237 reviewsModern/Spacious 2BR/2BA West Town
Condo in Chicago
4.87 out of 5 average rating, 443 reviewsHumboldt Park Traveler's Lodge
Condo in Chicago
4.91 out of 5 average rating, 251 reviewsOld Town Pied-à-Terre w/Pvt Terrace and Parking
Condo in Chicago
4.92 out of 5 average rating, 117 reviewsStunning, Spacious, & Sun-Soaked 1br Uptown Condo
Condo in Chicago
4.82 out of 5 average rating, 313 reviewsLively Wicker Park 2br, Steps to Damen Blue Line
Pet-friendly condo rentals
Condo in Evanston
4.77 out of 5 average rating, 575 reviewsSpacious Evanston Unit - Walk to Northwestern U
Condo in Chicago
4.99 out of 5 average rating, 223 reviews❤︎ of Lincoln Park | 11ft Ceiling | 1,750ft² | W/D
Condo in Chicago
4.93 out of 5 average rating, 194 reviewsPvt 1bdr Rogers Park, Loyola, Northwestern.
Condo in Chicago
4.94 out of 5 average rating, 178 reviewsCharming Chinatown Home by McCormick★Downtown
Condo in Chicago
4.83 out of 5 average rating, 315 reviewsChic and Charming Vintage Condominium in Lincoln Park
Condo in Chicago
4.9 out of 5 average rating, 105 reviewsModern designed 2bed/2bath | Heart of Bronzeville!
Condo in Chicago
4.78 out of 5 average rating, 203 reviewsModern Luxury In Old Town - Sleeps 4
Condo in Chicago
4.8 out of 5 average rating, 173 reviewsMICH AVE #5|Safe DTown Grant Park, Museums 2bd/2ba
Condo rentals with a pool
Condo in Chicago
4.74 out of 5 average rating, 152 reviewsCentral Downtown Location-Modern 2BR Condo
Condo in Evanston
4.92 out of 5 average rating, 107 reviewsChicago's Treasure "Heart of Evanston" 2bdr +1 Ba
Condo in Lisle
4.92 out of 5 average rating, 50 reviewsPeaceful Condo in Lisle, Illinois
Condo in Elk Grove Village
4.95 out of 5 average rating, 59 reviewsJust remodeled apartment close to airport and mall
Condo in Downers Grove
4.88 out of 5 average rating, 52 reviewsUpscale, Smoke and Pet Free, Washer Dryer, Balcony
Condo in Chicago
4.8 out of 5 average rating, 20 reviewsLovely condo studio
Condo in Chicago
4.68 out of 5 average rating, 28 reviews1 bedroom in the heart of downtown Chicago.
Private room in Hillside
Lovely Guest Room W private bath rm.
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