Holiday homes in Chicago
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Top-rated holiday homes in 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 Chicago condo rentals
Weekly condo rentals
Condo in Oak Park
4.79 out of 5 average rating, 312 reviewsPeaceful Oak Park Condo Next to Green Line Metro
Condo in Oak Park
4.88 out of 5 average rating, 164 reviewsAttractive Flat - Historic Oak Park
Condo in Chicago
4.98 out of 5 average rating, 211 reviewsNear Lake Michigan & Wrigley Field
Condo in Oak Park
4.96 out of 5 average rating, 134 reviewsPicture Perfect 3Bed Steps from Train and FLW
Condo in Chicago
4.91 out of 5 average rating, 251 reviewsOld Town Pied-à-Terre w/Pvt Terrace and Parking
Condo in Chicago
4.98 out of 5 average rating, 262 reviewsNorthside Chicago Favorite with parking!
Condo in Chicago
4.81 out of 5 average rating, 447 reviewsCozy Apartment with Free On-Site Parking
Condo in Chicago
4.86 out of 5 average rating, 123 reviewsQuiet, Modern, Convenient 2 bedroom condo
Pet-friendly condo rentals
Condo in Evanston
4.77 out of 5 average rating, 574 reviewsSpacious Evanston Unit - Walk to Northwestern U
Condo in Chicago
4.88 out of 5 average rating, 240 reviews2 King Bed Condo Easy Downtown Free Street Parking
Condo in Chicago
4.93 out of 5 average rating, 194 reviewsPvt 1bdr Rogers Park, Loyola, Northwestern.
Condo in Chicago
4.93 out of 5 average rating, 114 reviewsClifton Garden Oasis 1 Min Walk to Wrigley
Condo in Chicago
4.91 out of 5 average rating, 305 reviewsSusie's Space. 2BR easy parking & pet friendly
Condo in Chicago
4.83 out of 5 average rating, 314 reviewsChic and Charming Vintage Condominium in Lincoln Park
Condo in Chicago
4.82 out of 5 average rating, 185 reviewsCan't Beat This 2min Walk to Wrigley!
Condo in Chicago
4.95 out of 5 average rating, 132 reviewsThe Grand Kimball Lodge, Logan Square, Sleeps 14
Condo rentals with a pool
Condo in The Loop
4.74 out of 5 average rating, 152 reviewsCentral Downtown Location-Modern 2BR Condo
Condo in Evanston
4.91 out of 5 average rating, 105 reviewsChicago's Treasure "Heart of Evanston" 2bdr +1 Ba
Condo in Elk Grove Village
4.95 out of 5 average rating, 57 reviewsJust remodeled apartment close to airport and mall
Condo in Lisle
4.92 out of 5 average rating, 49 reviewsPeaceful Condo in Lisle, Illinois
Condo in Lombard
4.85 out of 5 average rating, 46 reviewsSmoke & Pet Free, Washer Dryer, Fireplace, 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.
Room in Naperville
4.5 out of 5 average rating, 6 reviewsPrivate Bedroom with Private Bath - 2nd floor
Quick stats about condo rentals in Chicago
Total rentals
1.1K properties
Rentals with dedicated workspaces
630 properties have a dedicated workspace
Rentals with a pool
100 properties have a pool
Pet-friendly rentals
300 properties allow pets
Family-friendly rentals
640 properties are a good fit for families
Total number of reviews
61K reviews
Destinations to explore
- Downtown Chicago Holiday rentals
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- Lake Geneva Accommodation & holiday rentals
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- Rentals with a home theatre Chicago
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