Apartment holiday rentals in Chicago
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Top-rated apartment rentals in Chicago
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Holiday rentals for every style
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Popular amenities for Chicago apartment rentals
Weekly apartment rentals
Apartment in Chicago
4.98 out of 5 average rating, 307 reviewsRedesigned Lower Level Studio in Historic Building
Apartment in Forest Park
5.0 out of 5 average rating, 232 reviewsLike a Treehouse!
Apartment in Lincoln Square
4.96 out of 5 average rating, 324 reviewsBright family-friendly Lincoln Square 2-bed 1-bath
Apartment in Chicago
4.98 out of 5 average rating, 203 reviewsSpacious 2BR on Quiet St - Free Park/Late Checkout
Apartment in Oak Park
4.97 out of 5 average rating, 169 reviewsChic Retreat in Historic Victorian House-Park Free
Apartment in Lake View
4.86 out of 5 average rating, 205 reviewsPrivate Queen Bedroom and En Suite Bath
Apartment in Chicago
4.93 out of 5 average rating, 173 reviewsCharming Apt. near Wrigley/Cubs, Ravenswood/Uptown
Apartment in Near North Side
4.82 out of 5 average rating, 490 reviewsGreat Location Studio II
Private apartment rentals
Apartment in Irving Park
4.96 out of 5 average rating, 255 reviewsSpacious 1BR apartment in a central location
Apartment in Chicago
4.96 out of 5 average rating, 382 reviewsKing Bed, Huge Spa Shower, Dining Destination
Apartment in Logan Square
4.83 out of 5 average rating, 485 reviewsRelaxed Bucktown/Wicker Park 1B Apt
Apartment in Forest Park
4.93 out of 5 average rating, 603 reviewsPeaceful oasis in Forest Park
Apartment in Logan Square
4.97 out of 5 average rating, 260 reviewsLogan Square 2nd Floor Chicago Victorian
Apartment in Chicago
4.98 out of 5 average rating, 139 reviewsModern Apt with style & comfort in Pilsen Chicago
Apartment in Chicago
4.84 out of 5 average rating, 178 reviewsLa Cottage
Apartment in Chicago
4.89 out of 5 average rating, 249 reviewsModern
Apartment rentals with a hot tub
Apartment in Chicago
4.88 out of 5 average rating, 402 reviewsCheckerboard Studio with Private Outdoor Hot Tub and Yard
Apartment in Chicago
4.87 out of 5 average rating, 165 reviewsSkyline Serenity: Sauna, Hot Tub, Peloton, Views
Apartment in Berwyn
4.91 out of 5 average rating, 209 reviews“Dream slice of urban homesteading.”
Apartment in Chicago
4.92 out of 5 average rating, 38 reviewsLuxe Suite + Spa House Retreat! Pets Welcome
Apartment in Chicago
5.0 out of 5 average rating, 12 reviewsLake, City, & River View Condo
Apartment in The Loop
4.8 out of 5 average rating, 10 reviewsThe Areal Oasis
Apartment in Chicago
4.8 out of 5 average rating, 25 reviewsSpacious Beautiful Condo
Apartment in West Loop
New place to stayCloud9 | Co-Working+Golf|@Fulton Market |The Boho
Quick stats about apartment 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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- Rentals with a sauna Chicago
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