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
Flat in Chicago
4.92 out of 5 average rating, 497 reviews2BR Bursting w/ Character in Hip Logan Square!
Flat in Lincoln Square
4.96 out of 5 average rating, 324 reviewsBright family-friendly Lincoln Square 2-bed 1-bath
Flat in Chicago
4.94 out of 5 average rating, 195 reviewsSpacious, light-drenched studio-private entrance!
Flat in Chicago
4.88 out of 5 average rating, 145 reviewsCharming Gold Coast One-Bedroom Near Downtown!
Flat in Forest Park
5.0 out of 5 average rating, 232 reviewsLike a Treehouse!
Flat in Chicago
4.96 out of 5 average rating, 383 reviewsKing Bed, Huge Spa Shower, Dining Destination
Flat in Chicago
4.98 out of 5 average rating, 140 reviewsModern Apt with style & comfort in Pilsen Chicago
Flat in Chicago
4.98 out of 5 average rating, 257 reviewsAndersonville Cozy 1 bedroom basement suite
Private apartment rentals
Flat in Little Italy
4.98 out of 5 average rating, 203 reviewsSpacious 2BR on Quiet St - Free Park/Late Checkout
Flat in Chicago
4.95 out of 5 average rating, 204 reviewsFree Parking & King Bed in Desirable Norwood Park!
Flat in Near North Side
4.82 out of 5 average rating, 490 reviewsGreat Location Studio II
Flat in Chicago
4.78 out of 5 average rating, 139 reviewsRoomy Getaway in Vibrant Center of Lincoln Park
Flat in Lake View
4.86 out of 5 average rating, 205 reviewsPrivate Queen Bedroom and En Suite Bath
Flat in Logan Square
4.89 out of 5 average rating, 351 reviewsSunny Logan Square Artists' home
Flat in Forest Park
4.93 out of 5 average rating, 603 reviewsPeaceful oasis in Forest Park
Flat in Logan Square
4.97 out of 5 average rating, 260 reviewsLogan Square 2nd Floor Chicago Victorian
Apartment rentals with a hot tub
Flat in Chicago
4.88 out of 5 average rating, 402 reviewsCheckerboard Studio with Private Outdoor Hot Tub and Yard
Flat in Chicago
4.87 out of 5 average rating, 165 reviewsSkyline Serenity: Sauna, Hot Tub, Peloton, Views
Flat in Berwyn
4.91 out of 5 average rating, 209 reviews“Dream slice of urban homesteading.”
Flat in Chicago
4.87 out of 5 average rating, 108 reviewsCloud9 |XL Penthouse+Movie Theater+Gym |The Harper
Flat in Chicago
4.92 out of 5 average rating, 38 reviewsLuxe Suite + Spa House Retreat! Pets Welcome
Flat in Chicago
5.0 out of 5 average rating, 12 reviewsLake, City, & River View Condo
Flat in Chicago
4.8 out of 5 average rating, 25 reviewsSpacious Beautiful Condo
Flat in Chicago
4.83 out of 5 average rating, 30 reviewsThe Professional's Playground
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
- Serviced apartment rentals United States
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