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 Humboldt Park
4.98 out of 5 average rating, 111 reviewsHumboldt Park Loft
Apartment in Oak Park
4.86 out of 5 average rating, 234 reviewsCozy and Character-Rich Chicago Style, Tv NFL PASS
Apartment in Chicago
4.81 out of 5 average rating, 139 reviewsChic & Fully Furnished Studio Apt with Laundry
Apartment in Chicago
4.96 out of 5 average rating, 383 reviewsKing Bed, Huge Spa Shower, Dining Destination
Apartment in Chicago
4.95 out of 5 average rating, 117 reviewsComfortable, modern apartment 20 Min from Downtown
Apartment in Lincoln Square
4.96 out of 5 average rating, 324 reviewsBright family-friendly Lincoln Square 2-bed 1-bath
Apartment in Berwyn
4.87 out of 5 average rating, 151 reviewsThe Green Bungalow: Charming 1-BR apt. with patio
Apartment in Forest Park
4.93 out of 5 average rating, 605 reviewsPeaceful oasis in Forest Park
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
4.87 out of 5 average rating, 108 reviewsCloud9 |XL Penthouse+Movie Theater+Gym |The Harper
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 Chicago
4.83 out of 5 average rating, 30 reviewsThe Professional's Playground
Apartment in Chicago
4.8 out of 5 average rating, 25 reviewsSpacious Beautiful Condo
Weekly apartment rentals
Apartment in Chicago
4.89 out of 5 average rating, 250 reviewsModern
Apartment in Chicago
4.78 out of 5 average rating, 139 reviewsRoomy Getaway in Vibrant Center of Lincoln Park
Apartment in Chicago
4.92 out of 5 average rating, 334 reviewsBright, Modern Apartment in a Vintage Greystone
Apartment in Chicago
4.83 out of 5 average rating, 485 reviewsRelaxed Bucktown/Wicker Park 1B Apt
Apartment in Chicago
4.98 out of 5 average rating, 203 reviewsSpacious 2BR on Quiet St - Free Park/Late Checkout
Apartment in Chicago
4.91 out of 5 average rating, 380 reviewsThe Grotto of Logan Square
Apartment in Chicago
4.89 out of 5 average rating, 380 reviewsGreat Location Studio in the Gold Coast!!
Apartment in Chicago
4.9 out of 5 average rating, 375 reviewsRelax and Enjoy Chicago in an Updated and Private Apartment in Roscoe Village
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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