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
4.96 out of 5 average rating, 130 reviewsPicture Perfect 3Bed Steps from Train and FLW
Condo in Chicago
4.86 out of 5 average rating, 120 reviewsQuiet, Modern, Convenient 2 bedroom condo
Condo in Chicago
4.96 out of 5 average rating, 128 reviewsEast Lakeview Designer Condo with 2 Bd, 2 Bath
Condo in Chicago
4.88 out of 5 average rating, 236 reviews2 King Bed Condo Easy Downtown Free Street Parking
Condo in Chicago
4.98 out of 5 average rating, 236 reviewsUrban Luxury 1BR/2BA Logan Square Condo w/Garage
Condo in Chicago
4.9 out of 5 average rating, 137 reviewsEast Garfield Park 2 Bedroom
Condo in Chicago
4.98 out of 5 average rating, 208 reviewsNear Lake Michigan & Wrigley Field
Condo in Chicago
4.83 out of 5 average rating, 181 reviewsCan't Beat This 2min Walk to Wrigley!
Pet-friendly condo rentals
Condo in Evanston
4.77 out of 5 average rating, 570 reviewsSpacious Evanston Unit - Walk to Northwestern U
Condo in Chicago
4.99 out of 5 average rating, 217 reviews❤︎ of Lincoln Park | 11ft Ceiling | 1,750ft² | W/D
Condo in Chicago
4.94 out of 5 average rating, 111 reviewsClifton Garden Oasis 1 Min Walk to Wrigley
Condo in Chicago
4.91 out of 5 average rating, 301 reviewsSusie's Space. 2BR easy parking & pet friendly
Condo in Chicago
4.83 out of 5 average rating, 311 reviewsChic and Charming Vintage Condominium in Lincoln Park
Condo in Chicago
4.78 out of 5 average rating, 202 reviewsModern Luxury In Old Town - Sleeps 4
Condo in Chicago
4.82 out of 5 average rating, 118 reviewsCharming Condo near U.C./Loop/McCormick Place
Condo in Chicago
4.92 out of 5 average rating, 101 reviewsModern designed 2bed/2bath | Heart of Bronzeville!
Condo rentals with a pool
Condo in Chicago
4.74 out of 5 average rating, 148 reviewsCentral Downtown Location-Modern 2BR Condo
Condo in Evanston
4.91 out of 5 average rating, 104 reviewsChicago's Treasure "Heart of Evanston" 2bdr +1 Ba
Condo in Lisle
4.96 out of 5 average rating, 45 reviewsPeaceful Condo in Lisle, Illinois
Condo in Elk Grove Village
4.95 out of 5 average rating, 56 reviewsJust remodeled apartment close to airport and mall
Condo in Lombard
4.97 out of 5 average rating, 36 reviewsPond View, Washer Dryer, Non Smoking, Pet Free
Condo in Chicago
4.78 out of 5 average rating, 18 reviewsLovely condo studio
Condo in Near North Side
4.31 out of 5 average rating, 16 reviewsLovely one bedroom condo River north
Room in Hillside
Lovely Guest Room W private bath rm.
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
- Evanston Accommodation & holiday rentals
- Holland Accommodation & holiday rentals
- South Haven Holiday rentals
- Naperville Accommodation & holiday rentals
- South Side Accommodation & holiday rentals
- South Bend Accommodation & holiday rentals
- New Buffalo Holiday rentals
- Rentals with an EV charger Chicago
- Rentals with a fireplace Chicago
- Rentals with a washing machine and dryer Chicago
- Rentals with an accessible height toilet Chicago
- Rentals with a home theatre Chicago
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- Rentals with a fire pit Chicago
- Mansion rentals Chicago
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- Hotel rentals Chicago
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- Bed and breakfasts Chicago
- Boutique hotel rentals Chicago
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- Condo rentals Downtown Chicago
- Condo rentals Milwaukee
- Condo rentals Lake Geneva
- Condo rentals Illinois
- Condo rentals Cook County
- Yurt Rentals United States
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