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
4.91 out of 5 average rating, 233 reviewsModern/Spacious 2BR/2BA West Town
Nov. 13 – 20
Condo in Chicago
4.95 out of 5 average rating, 130 reviewsGrand Avenue Apt 2/west Loop & Newly Renovated!
Condo in Chicago
4.87 out of 5 average rating, 117 reviewsQuiet, Modern, Convenient 2 bedroom condo
Oct. 15 – 22
Condo in Gold Coast
4.9 out of 5 average rating, 167 reviews2BD/2BA MAG MILE MASTERPIECE (+Rooftop)
May 7 – 14
Condo in Little Italy
4.96 out of 5 average rating, 118 reviewsPrivate hot tub - King bed suite - Free parking
Jul. 30 – Aug. 6
Condo in Oak Park
4.88 out of 5 average rating, 163 reviewsAttractive Flat - Historic Oak Park
Sep. 15 – 22
Condo in Chicago
4.81 out of 5 average rating, 444 reviewsCozy Apartment with Free On-Site Parking
Oct. 17 – 24
Condo in Wrigleyville
4.97 out of 5 average rating, 119 reviewsWrigleyville Inn. Historic Greystone. Parking pass
Jan. 6 – 13
Pet-friendly condo rentals
Condo in Evanston
4.76 out of 5 average rating, 565 reviewsSpacious Evanston Unit - Walk to Northwestern U
Dec. 2 – 9
Condo in Chicago
4.83 out of 5 average rating, 307 reviewsChic and Charming Vintage Condominium in Lincoln Park
Jan. 29 – Feb. 5
Condo in Chicago
4.94 out of 5 average rating, 111 reviewsClifton Garden Oasis 1 Min Walk to Wrigley
Sep. 15 – 22
Condo in Chicago
4.99 out of 5 average rating, 212 reviews❤︎ of Lincoln Park | 11ft Ceiling | 1,750ft² | W/D
Mar. 16 – 23
Condo in Chicago
4.91 out of 5 average rating, 296 reviewsSusie's Space. 2BR easy parking & pet friendly
Jul. 19 – 26
Condo in Lincoln Park
4.78 out of 5 average rating, 199 reviewsModern Luxury In Old Town - Sleeps 4
Nov. 18 – 25
Condo in Chicago
4.82 out of 5 average rating, 177 reviewsCan't Beat This 2min Walk to Wrigley!
Nov. 21 – 28
Condo in The Loop
4.77 out of 5 average rating, 160 reviewsSafe Dtown Park VIEWS| Mich Ave, Museums 2bd/2ba
Sep. 20 – 27
Condo rentals with a pool
Condo in Chicago
4.75 out of 5 average rating, 145 reviewsCentral Downtown Location-Modern 2BR Condo
Jul. 3 – 10
Condo in Evanston
4.91 out of 5 average rating, 102 reviewsChicago's Treasure "Heart of Evanston" 2bdr +1 Ba
Dec. 9 – 16
Condo in Lisle
4.95 out of 5 average rating, 42 reviewsPeaceful Condo in Lisle, Illinois
Feb. 8 – 15
Condo in Elk Grove Village
4.95 out of 5 average rating, 56 reviewsJust remodeled apartment close to airport and mall
Nov. 21 – 28
Condo in Lombard
4.97 out of 5 average rating, 36 reviewsPond View, Washer Dryer, Non Smoking, Pet Free
Sep. 27 – Oct. 4
Condo in Chicago
4.75 out of 5 average rating, 16 reviewsLovely condo studio
Jan. 29 – Feb. 5
Condo in Near North Side
4.7 out of 5 average rating, 27 reviews1 bedroom in the heart of downtown Chicago.
Jul. 7 – 14
Room in Hillside
Lovely Guest Room W private bath rm.
Jul. 2 – 9
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