Apartment holiday rentals in Chicago
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Top-rated apartment rentals in Chicago
Guests agree: these apartments are highly rated for location, cleanliness and more.
Holiday rentals for every style
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Popular amenities for Chicago apartment rentals
Weekly apartment rentals
Apartment in Chicago
4.92 out of 5 average rating, 293 reviewsBright 2br Apt W/ Private Entrance & Laundry
5–12 Feb
Apartment in Wrigleyville
4.97 out of 5 average rating, 119 reviewsWrigleyville Inn. Historic Greystone. Parking pass
6–13 Jan
Apartment in Chicago
4.81 out of 5 average rating, 444 reviewsCozy Apartment with Free On-Site Parking
17–24 Oct
Apartment in Chicago
4.87 out of 5 average rating, 117 reviewsQuiet, Modern, Convenient 2 bedroom condo
15–22 Oct
Apartment in Chicago
4.98 out of 5 average rating, 201 reviewsNear Lake Michigan & Wrigley Field
27 Sep – 4 Oct
Apartment in Oak Park
4.79 out of 5 average rating, 308 reviewsPeaceful Oak Park Condo Next to Green Line Metro
13–20 Oct
Apartment in Chicago
4.96 out of 5 average rating, 112 reviewsBest Lincoln Square location. Spacious 2 bedroom
11–18 Jan
Apartment in Chicago
4.95 out of 5 average rating, 130 reviewsGrand Avenue Apt 2/west Loop & Newly Renovated!
Pet-friendly apartment rentals
Apartment in Evanston
4.76 out of 5 average rating, 565 reviewsSpacious Evanston Unit - Walk to Northwestern U
2–9 Dec
Apartment in Chicago
4.94 out of 5 average rating, 111 reviewsClifton Garden Oasis 1 Min Walk to Wrigley
17–24 Nov
Apartment in Chicago
4.83 out of 5 average rating, 307 reviewsChic and Charming Vintage Condominium in Lincoln Park
29 Jan – 5 Feb
Apartment in Chicago
4.91 out of 5 average rating, 296 reviewsSusie's Space. 2BR easy parking & pet friendly
19–26 Jul
Apartment in Chicago
4.99 out of 5 average rating, 211 reviews❤︎ of Lincoln Park | 11ft Ceiling | 1,750ft² | W/D
16–23 Mar
Apartment in Chicago
4.82 out of 5 average rating, 176 reviewsCan't Beat This 2min Walk to Wrigley!
21–28 Nov
Apartment in Chicago
4.78 out of 5 average rating, 199 reviewsModern Luxury In Old Town - Sleeps 4
18–25 Nov
Apartment in Chicago
4.95 out of 5 average rating, 128 reviewsThe Grand Kimball Lodge, Logan Square, Sleeps 14
11–18 Jan
Apartment rentals with a pool
Apartment in Chicago
4.75 out of 5 average rating, 144 reviewsCentral Downtown Location-Modern 2BR Condo
3–10 Jul
Apartment in Evanston
4.91 out of 5 average rating, 102 reviewsChicago's Treasure "Heart of Evanston" 2bdr +1 Ba
9–16 Dec
Apartment in Lisle
4.95 out of 5 average rating, 41 reviewsPeaceful Condo in Lisle, Illinois
12–19 Mar
Apartment in Elk Grove Village
4.95 out of 5 average rating, 56 reviewsJust remodeled apartment close to airport and mall
21–28 Nov
Apartment in Lombard
4.97 out of 5 average rating, 36 reviewsPond View, Washer Dryer, Non Smoking, Pet Free
27 Sep – 4 Oct
Apartment in Chicago
4.75 out of 5 average rating, 16 reviewsLovely condo studio
29 Jan – 5 Feb
Apartment in Chicago
4.7 out of 5 average rating, 27 reviews1 bedroom in the heart of downtown Chicago.
7–14 Jul
Room in Naperville
4.5 out of 5 average rating, 6 reviewsPrivate Bedroom with Private Bath - 2nd floor
6–13 Jan
Quick stats about apartment rentals in Chicago
Total rentals
1.1T 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
61T reviews
Destinations to explore
- Downtown Chicago Holiday rentals
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