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
Get the amount of space that is right for you
Popular amenities for Chicago apartment rentals
Weekly apartment rentals
Flat in West Town
4.89 out of 5 average rating, 473 reviewsiKlektik House Chicago / Robin
27 Dec – 3 Jan
Flat in Chicago
4.93 out of 5 average rating, 207 reviewsCozy Private Coach House
4–11 Oct
Flat in Irving Park
4.89 out of 5 average rating, 176 reviewsHistoric Chicago neighborhood flat
10–17 Nov
Flat in Oak Park
4.89 out of 5 average rating, 333 reviewsCharming Chicago-Style, Vintage, Tv NFL PASS
17–24 Jan
Flat in Forest Park
4.93 out of 5 average rating, 584 reviewsPeaceful oasis in Forest Park
3–10 Sept
Flat in Andersonville
4.98 out of 5 average rating, 249 reviewsAndersonville Cozy 1 bedroom basement suite
30 Oct – 6 Nov
Flat in Logan Square
4.87 out of 5 average rating, 484 reviewsLogan Square Studio
6–13 Feb
Flat in Logan Square
4.96 out of 5 average rating, 255 reviewsLogan Square 2nd Floor Chicago Victorian
17–24 Dec
Private apartment rentals
Flat in Chicago
4.9 out of 5 average rating, 283 reviewsModern Logan Square Apartment, steps from train!
19–26 Apr
Flat in Lake View
4.86 out of 5 average rating, 201 reviewsPrivate Queen Bedroom and En Suite Bath
14–21 Jul
Flat in Chicago
4.95 out of 5 average rating, 106 reviewsComfortable, modern apartment 20 Min from Downtown
19–26 Nov
Flat in Forest Park
5.0 out of 5 average rating, 219 reviewsLike a Treehouse!
5–12 Sept
Flat in Logan Square
4.81 out of 5 average rating, 105 reviewsWelcome Chez Moi
13–20 Aug
Flat in Chicago
4.84 out of 5 average rating, 175 reviewsLa Cottage
3–10 Oct
Flat in Chicago
4.93 out of 5 average rating, 381 reviewsRavenswood Guest House Annex
21–28 Apr
Flat in Chicago
4.98 out of 5 average rating, 188 reviewsFoster Flat - Retreat to your Home Away from Home
Apartment rentals with a hot tub
Flat in Chicago
4.88 out of 5 average rating, 393 reviewsCheckerboard Studio with Private Outdoor Hot Tub and Yard
9–16 Oct
Flat in Berwyn
4.91 out of 5 average rating, 202 reviews“Dream slice of urban homesteading.”
10–17 Feb
Flat in Chicago
4.86 out of 5 average rating, 155 reviewsStunning Panoramic Chicago Views & Free Parking
4–11 Oct
Flat in West Loop
4.87 out of 5 average rating, 106 reviewsCloud9 |XL Penthouse+Movie Theater+Gym |The Harper
15–22 May
Flat in Chicago
4.93 out of 5 average rating, 28 reviewsLuxe Suite + Spa House Retreat! Pets Welcome
13–20 Nov
Flat in Chicago
5.0 out of 5 average rating, 16 reviewsSpacious Beautiful Condo
14–21 Oct
Flat in Streeterville
5.0 out of 5 average rating, 9 reviewsLake, City, & River View Condo
6–13 May
Flat in Chicago
4.79 out of 5 average rating, 24 reviewsThe Professional's Playground
2–9 Jan
Quick stats about flat rentals in Chicago
Total rentals
5.9K properties
Rentals with dedicated workspaces
3.8K properties have a dedicated workspace
Rentals with a pool
750 properties have a pool
Pet-friendly rentals
2K properties allow pets
Family-friendly rentals
2.7K properties are a good fit for families
Total number of reviews
253K reviews
Destinations to explore
- Downtown Chicago Holiday rentals
- Milwaukee Holiday rentals
- Lake Geneva Holiday rentals
- Lake Michigan Beach Holiday rentals
- Saugatuck Holiday rentals
- Evanston Holiday rentals
- Holland Holiday rentals
- South Haven Holiday rentals
- Naperville Holiday rentals
- South Side Holiday rentals
- South Bend Holiday rentals
- New Buffalo Holiday rentals
- Flat rentals United States
- Serviced apartment rentals United States
- Rentals with a hot tub Chicago
- Pet-friendly rentals Chicago
- Rentals with pools Chicago
- Rentals with a fireplace Chicago
- Apartment rentals Chicago
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- Rentals with a washing machine and dryer Chicago
- Family-friendly rentals Chicago
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- Smoking-friendly rentals Chicago
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- Flat rentals Downtown Chicago
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- Yurt Rentals United States
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