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 Woodlawn
4.9 out of 5 average rating, 190 reviewsA Stones Throw from U Chicago South Campus!
11 – 18 Jan
Condo in Chicago
4.81 out of 5 average rating, 444 reviewsCozy Apartment with Free On-Site Parking
1 – 8 Oct
Condo in Chicago
4.95 out of 5 average rating, 130 reviewsGrand Avenue Apt 2/west Loop & Newly Renovated!
Condo in Chicago
4.87 out of 5 average rating, 117 reviewsQuiet, Modern, Convenient 2 bedroom condo
27 Aug – 3 Sept
Condo in Chicago
4.83 out of 5 average rating, 307 reviewsChic and Charming Vintage Condominium in Lincoln Park
4 – 11 Dec
Condo in Little Italy
4.96 out of 5 average rating, 118 reviewsPrivate hot tub - King bed suite - Free parking
12 – 19 Sept
Condo in Oak Park
4.79 out of 5 average rating, 308 reviewsPeaceful Oak Park Condo Next to Green Line Metro
12 – 19 Oct
Condo in Chicago
4.98 out of 5 average rating, 201 reviewsNear Lake Michigan & Wrigley Field
14 – 21 Oct
Pet-friendly condo rentals
Condo in Evanston
4.76 out of 5 average rating, 565 reviewsSpacious Evanston Unit - Walk to Northwestern U
27 Oct – 3 Nov
Condo in Chicago
4.94 out of 5 average rating, 111 reviewsClifton Garden Oasis 1 Min Walk to Wrigley
1 – 8 Nov
Condo in Chicago
4.78 out of 5 average rating, 199 reviewsModern Luxury In Old Town - Sleeps 4
29 Jan – 5 Feb
Condo in Lincoln Park
4.99 out of 5 average rating, 211 reviews❤︎ of Lincoln Park | 11ft Ceiling | 1,750ft² | W/D
16 – 23 Mar
Condo in Chicago
4.91 out of 5 average rating, 296 reviewsSusie's Space. 2BR easy parking & pet friendly
11 – 18 July
Condo in Chicago
4.82 out of 5 average rating, 176 reviewsCan't Beat This 2min Walk to Wrigley!
11 – 18 Mar
Condo in Chicago
4.82 out of 5 average rating, 117 reviewsCharming Condo near U.C./Loop/McCormick Place
3 – 10 Jan
Condo in The Loop
4.77 out of 5 average rating, 160 reviewsSafe Dtown Park VIEWS| Mich Ave, Museums 2bd/2ba
8 – 15 June
Condo rentals with a pool
Condo in The Loop
4.75 out of 5 average rating, 144 reviewsCentral Downtown Location-Modern 2BR Condo
30 June – 7 July
Condo in Evanston
4.91 out of 5 average rating, 102 reviewsChicago's Treasure "Heart of Evanston" 2bdr +1 Ba
25 Jan – 1 Feb
Condo in Lisle
4.95 out of 5 average rating, 41 reviewsPeaceful Condo in Lisle, Illinois
15 – 22 Oct
Condo in Elk Grove Village
4.95 out of 5 average rating, 56 reviewsJust remodeled apartment close to airport and mall
21 – 28 Nov
Condo in Lombard
4.97 out of 5 average rating, 36 reviewsPond View, Washer Dryer, Non Smoking, Pet Free
18 – 25 Oct
Condo in Chicago
4.75 out of 5 average rating, 16 reviewsLovely condo studio
12 – 19 Jan
Condo in Chicago
4.7 out of 5 average rating, 27 reviews1 bedroom in the heart of downtown Chicago.
11 – 18 July
Room in Naperville
4.5 out of 5 average rating, 6 reviewsPrivate Bedroom with Private Bath - 2nd floor
14 – 21 Aug
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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