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 Chicago
4.98 out of 5 average rating, 237 reviewsUrban Luxury 1BR/2BA Logan Square Condo w/Garage
Condo in Oak Park
4.78 out of 5 average rating, 311 reviewsPeaceful Oak Park Condo Next to Green Line Metro
Condo in Chicago
4.93 out of 5 average rating, 219 reviewsThe Upscale Getaway Near Downtown
Condo in Oak Park
4.88 out of 5 average rating, 164 reviewsAttractive Flat - Historic Oak Park
Condo in Chicago
4.81 out of 5 average rating, 447 reviewsCozy Apartment with Free On-Site Parking
Condo in Chicago
4.98 out of 5 average rating, 211 reviewsNear Lake Michigan & Wrigley Field
Condo in Chicago
4.96 out of 5 average rating, 130 reviewsEast Lakeview Designer Condo with 2 Bd, 2 Bath
Condo in Chicago
4.92 out of 5 average rating, 236 reviewsModern/Spacious 2BR/2BA West Town
Pet-friendly condo rentals
Condo in Evanston
4.76 out of 5 average rating, 573 reviewsSpacious Evanston Unit - Walk to Northwestern U
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
4.9 out of 5 average rating, 102 reviewsModern designed 2bed/2bath | Heart of Bronzeville!
Condo in Chicago
4.83 out of 5 average rating, 313 reviewsChic and Charming Vintage Condominium in Lincoln Park
Condo in Chicago
4.82 out of 5 average rating, 184 reviewsCan't Beat This 2min Walk to Wrigley!
Condo in Lincoln Park
4.78 out of 5 average rating, 203 reviewsModern Luxury In Old Town - Sleeps 4
Condo in Chicago
4.82 out of 5 average rating, 131 reviewsMassive Old Town Home Steps to Wells St & Beach
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
4.91 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, 48 reviewsPeaceful Condo in Lisle, Illinois
Condo in Lombard
4.95 out of 5 average rating, 38 reviewsPond View, Washer Dryer, Non Smoking, Pet Free
Condo in Chicago
4.79 out of 5 average rating, 19 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
- Milwaukee Holiday rentals
- Lake Geneva Accommodation & holiday rentals
- Lake Michigan Beach Accommodation & holiday rentals
- Saugatuck Accommodation & holiday rentals
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- New Buffalo Holiday rentals
- Rentals with a sauna Chicago
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