Apartment vacation 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.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Chicago apartment rentals
Apartment rentals with air conditioning
Apartment in Norwood Park
4.95 out of 5 average rating, 202 reviewsFree Parking & King Bed in Desirable Norwood Park!
Apartment in Chicago
4.87 out of 5 average rating, 488 reviewsLogan Square Studio
Apartment in Lincoln Square
4.96 out of 5 average rating, 324 reviewsBright family-friendly Lincoln Square 2-bed 1-bath
Apartment in Chicago
4.86 out of 5 average rating, 106 reviews⭐️⭐️Entire Unite 2-Bdr. HORNER PARK⭐️⭐️
Apartment in Chicago
4.96 out of 5 average rating, 382 reviewsKing Bed, Huge Spa Shower, Dining Destination
Apartment in Chicago
4.99 out of 5 average rating, 107 reviewsNewly Renovated, Spacious 2BR in Andersonville
Apartment in Andersonville
4.98 out of 5 average rating, 256 reviewsAndersonville Cozy 1 bedroom basement suite
Apartment in Chicago
4.89 out of 5 average rating, 479 reviewsiKlektik House Chicago / Robin
Apartment rentals with a hot tub
Apartment in Chicago
4.88 out of 5 average rating, 399 reviewsCheckerboard Studio with Private Outdoor Hot Tub and Yard
Apartment in Berwyn
4.91 out of 5 average rating, 208 reviews“Dream slice of urban homesteading.”
Apartment in Chicago
4.87 out of 5 average rating, 163 reviewsSkyline Serenity: Sauna, Hot Tub, Peloton, Views
Apartment in West Loop
4.87 out of 5 average rating, 107 reviewsCloud9 |XL Penthouse+Movie Theater+Gym |The Harper
Apartment in Chicago
4.92 out of 5 average rating, 37 reviewsLuxe Suite + Spa House Retreat! Pets Welcome
Apartment in The Loop
4.8 out of 5 average rating, 10 reviewsThe Areal Oasis
Apartment in Streeterville
5.0 out of 5 average rating, 11 reviewsLake, City, & River View Condo
Apartment in West Loop
5.0 out of 5 average rating, 11 reviewsSkyline Oasis: City & Lake Views
Weekly apartment rentals
Apartment in Logan Square
4.97 out of 5 average rating, 259 reviewsLogan Square 2nd Floor Chicago Victorian
Apartment in Chicago
4.9 out of 5 average rating, 287 reviewsModern Logan Square Apartment, steps from train!
Apartment in Chicago
4.89 out of 5 average rating, 347 reviewsSunny Logan Square Artists' home
Apartment in Oak Park
4.86 out of 5 average rating, 538 reviewsLong stays welcome@warm&cute vintage 2BR
Apartment in Berwyn
4.87 out of 5 average rating, 147 reviewsThe Green Bungalow: Charming 1-BR apt. with patio
Apartment in Oak Park
4.86 out of 5 average rating, 251 reviewsCosmopolitan Nest in Oak Park North Side
Apartment in Chicago
4.89 out of 5 average rating, 249 reviewsModern
Apartment in Chicago
4.87 out of 5 average rating, 276 reviewsHistoric Old Town Flat - Minutes from Downtown!
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
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