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 Forest Park
4.98 out of 5 average rating, 291 reviewsWalk to Oak Park from Our Sunny Turn of the Century Apt
Apartment in Chicago
4.87 out of 5 average rating, 488 reviewsLogan Square Studio
Apartment in Chicago
4.98 out of 5 average rating, 257 reviewsAndersonville Cozy 1 bedroom basement suite
Apartment in Oak Park
4.97 out of 5 average rating, 168 reviewsChic Retreat in Historic Victorian House-Park Free
Apartment in Chicago
4.96 out of 5 average rating, 382 reviewsKing Bed, Huge Spa Shower, Dining Destination
Apartment in Oak Park
4.86 out of 5 average rating, 538 reviewsLong stays welcome@warm&cute vintage 2BR
Apartment in Chicago
4.95 out of 5 average rating, 205 reviewsHuge Apt in Uptown/Andersonville
Apartment in Chicago
4.92 out of 5 average rating, 310 reviewsSpacious & private! Free parking! Great location!
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, 163 reviewsSkyline Serenity: Sauna, Hot Tub, Peloton, Views
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, 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 Chicago
5.0 out of 5 average rating, 12 reviewsLake, City, & River View Condo
Apartment in Chicago
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
Weekly apartment rentals
Apartment in Logan Square
4.9 out of 5 average rating, 289 reviewsModern Logan Square Apartment, steps from train!
Apartment in Chicago
4.86 out of 5 average rating, 188 reviewsCozy & Comfy 1bd In Historic Portage Park Bungalow
Apartment in Chicago
4.89 out of 5 average rating, 249 reviewsModern
Apartment in Chicago
4.8 out of 5 average rating, 389 reviews'Secret Garden' Apartment in Wrigleyville
Apartment in Logan Square
4.83 out of 5 average rating, 484 reviewsRelaxed Bucktown/Wicker Park 1B Apt
Apartment in Lake View
4.86 out of 5 average rating, 175 reviewsPrivate 2 Bedroom Malt Row, N Center, Wrigley Home
Apartment in Chicago
4.82 out of 5 average rating, 116 reviewsCozy Avondale apt right by Belmont blue line stop
Apartment in Chicago
4.86 out of 5 average rating, 107 reviews⭐️⭐️Entire Unite 2-Bdr. HORNER PARK⭐️⭐️
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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