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
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Popular amenities for Downtown Chicago condo rentals
Weekly condo rentals
Condo in Chicago
4.97 out of 5 average rating, 101 reviewsStylish 3BR + Free Parking 10-15mins from Downtown
Sep 3 – 10
Condo in Chicago
4.98 out of 5 average rating, 201 reviewsNear Lake Michigan & Wrigley Field
Sep 9 – 16
Condo in Chicago
4.86 out of 5 average rating, 437 reviewsHumboldt Park Traveler's Lodge
Jun 20 – 27
Condo in Chicago
4.91 out of 5 average rating, 233 reviewsModern/Spacious 2BR/2BA West Town
Dec 26 – Jan 2
Condo in Chicago
4.87 out of 5 average rating, 118 reviewsQuiet, Modern, Convenient 2 bedroom condo
Jun 25 – Jul 2
Condo in Chicago
4.9 out of 5 average rating, 136 reviewsEast Garfield Park 2 Bedroom
Dec 25 – Jan 1
Condo in Chicago
4.81 out of 5 average rating, 444 reviewsCozy Apartment with Free On-Site Parking
Oct 18 – 25
Condo in Oak Park
4.88 out of 5 average rating, 164 reviewsAttractive Flat - Historic Oak Park
Dec 21 – 28
Pet-friendly condo rentals
Condo in Evanston
4.76 out of 5 average rating, 568 reviewsSpacious Evanston Unit - Walk to Northwestern U
Oct 27 – Nov 3
Condo in Chicago
4.99 out of 5 average rating, 214 reviews❤︎ of Lincoln Park | 11ft Ceiling | 1,750ft² | W/D
Mar 16 – 23
Condo in Chicago
4.94 out of 5 average rating, 111 reviewsClifton Garden Oasis 1 Min Walk to Wrigley
Sep 17 – 24
Condo in Chicago
4.92 out of 5 average rating, 100 reviewsModern designed 2bed/2bath | Heart of Bronzeville!
Sep 6 – 13
Condo in Chicago
4.91 out of 5 average rating, 298 reviewsSusie's Space. 2BR easy parking & pet friendly
Jul 19 – 26
Condo in Chicago
4.78 out of 5 average rating, 200 reviewsModern Luxury In Old Town - Sleeps 4
Dec 11 – 18
Condo in Chicago
4.83 out of 5 average rating, 178 reviewsCan't Beat This 2min Walk to Wrigley!
Nov 26 – Dec 3
Condo in The Loop
4.8 out of 5 average rating, 168 reviewsMICH AVE #5|Safe DTown Grant Park, Museums 2bd/2ba
Aug 24 – 31
Condo rentals with a pool
Condo in Chicago
4.74 out of 5 average rating, 146 reviewsCentral Downtown Location-Modern 2BR Condo
Jul 7 – 14
Condo in Evanston
4.91 out of 5 average rating, 102 reviewsChicago's Treasure "Heart of Evanston" 2bdr +1 Ba
Dec 2 – 9
Condo in Lisle
4.95 out of 5 average rating, 42 reviewsPeaceful Condo in Lisle, Illinois
Mar 25 – Apr 1
Condo in Elk Grove Village
4.95 out of 5 average rating, 56 reviewsJust remodeled apartment close to airport and mall
Oct 20 – 27
Condo in Lombard
4.97 out of 5 average rating, 36 reviewsPond View, Washer Dryer, Non Smoking, Pet Free
Aug 30 – Sep 6
Condo in Chicago
4.7 out of 5 average rating, 27 reviews1 bedroom in the heart of downtown Chicago.
Jul 21 – 28
Condo in Chicago
4.75 out of 5 average rating, 16 reviewsLovely condo studio
Oct 15 – 22
Room in Naperville
4.5 out of 5 average rating, 6 reviewsPrivate Bedroom with Private Bath - 2nd floor
Dec 26 – Jan 2
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