
Condo holiday 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.
Holiday rentals for every style
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Popular amenities for Downtown Chicago condo rentals
Weekly condo rentals

Condo in Chicago
4.96 out of 5 average rating, 25 reviewsCity View 3BR Condo/Garage Parki

Condo in Chicago
4.96 out of 5 average rating, 47 reviewsNEW! Spacious Modern 5 BD Condo

Condo in Chicago
4.84 out of 5 average rating, 181 reviewsLoft-Like Wicker Park Condo Steps from the Cta!

Condo in Chicago
4.92 out of 5 average rating, 13 reviewsCozy, sunny, boho condo in Uptown/Sheridan Park

Condo in Chicago
4.79 out of 5 average rating, 29 reviewsSpacious condo with open floor plan and fireplace

Condo in Chicago
4.92 out of 5 average rating, 257 reviewsModern/Spacious 2BR/2BA West Town

Condo in Chicago
4.92 out of 5 average rating, 146 reviewsUltra clean/cozy condo, 10 mins south of Downtown!

Condo in Chicago
4.79 out of 5 average rating, 125 reviewsMarvelous Condo w/ Pri Prkng Cls to Transit &Beach
Pet-friendly condo rentals

Condo in Chicago
4.86 out of 5 average rating, 126 reviews816 PLZN Luxury Apt | Rooftop | Garage Parking

Condo in Chicago
4.93 out of 5 average rating, 107 reviewsThe Fox Den

Condo in Chicago
4.95 out of 5 average rating, 105 reviewsThe Bagel Inn - Bright & Modern Wrigleyville 2 Bed

Condo in Chicago
4.89 out of 5 average rating, 108 reviewsUnique 2BR/2BA FREE Parking/WI-FI Minutes From DT

Condo in Chicago
4.85 out of 5 average rating, 124 reviewsDowntown Mich Ave #7| Park View Penthouse +gym

Condo in Chicago
4.82 out of 5 average rating, 135 reviewsSpacious Home, Incredible Lakeview Location

Condo in Chicago
4.92 out of 5 average rating, 221 reviewsPvt 1bdr Rogers Park, Loyola, Northwestern.

Condo in Chicago
4.91 out of 5 average rating, 329 reviewsSusie's Space. 2BR easy parking & pet friendly
Condo rentals with a pool

Condo in Evanston
4.95 out of 5 average rating, 87 reviews"Joy of Evanston" 1BDR, KING EXEC Suite, pool+Gym

Condo in Chicago
4.71 out of 5 average rating, 41 reviews2BD Central Downtown Location! Spacious & Cozy

Condo in Chicago
New place to stayvoco: Balcony & City View

Condo in Elk Grove Village
4.95 out of 5 average rating, 78 reviewsJust remodeled apartment close to airport and mall

Condo in Evanston
4.91 out of 5 average rating, 120 reviewsChicago's Treasure "Heart of Evanston" 2bdr +1 Ba

Condo in Chicago
4.8 out of 5 average rating, 25 reviewsLovely condo studio

Condo in Evanston
4.96 out of 5 average rating, 94 reviews"Unity of Evanston" 3 BDR+2BA ModernLuxe +pool
Destinations to explore
- Milwaukee Holiday rentals
- Lake Geneva Holiday rentals
- West Side Holiday rentals
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- Lake Michigan Beach Holiday rentals
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