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 Logan Square
4.87 out of 5 average rating, 487 reviewsLogan Square Studio
Apartment in Portage Park
4.96 out of 5 average rating, 113 reviewsComfortable, modern apartment 20 Min from Downtown
Apartment in Edgewater
4.93 out of 5 average rating, 383 reviewsRavenswood Guest House Annex
Apartment in Forest Park
4.93 out of 5 average rating, 593 reviewsPeaceful oasis in Forest Park
Apartment in Lake View
4.93 out of 5 average rating, 171 reviewsCharming Apt. near Wrigley/Cubs, Ravenswood/Uptown
Apartment in Andersonville
4.98 out of 5 average rating, 254 reviewsAndersonville Cozy 1 bedroom basement suite
Apartment in Oak Park
4.97 out of 5 average rating, 166 reviewsChic Retreat in Historic Victorian House-Park Free
Apartment in Chicago
4.98 out of 5 average rating, 191 reviewsFoster Flat - Retreat to your Home Away from Home
Apartment rentals with a hot tub
Apartment in West Town
4.88 out of 5 average rating, 398 reviewsCheckerboard Studio with Private Outdoor Hot Tub and Yard
Apartment in Berwyn
4.91 out of 5 average rating, 206 reviews“Dream slice of urban homesteading.”
Apartment in Near South Side
4.87 out of 5 average rating, 160 reviewsSkyline Serenity: Sauna, Hot Tub, Peloton, Views
Apartment in West Loop
4.87 out of 5 average rating, 106 reviewsCloud9 |XL Penthouse+Movie Theater+Gym |The Harper
Apartment in Logan Square
4.92 out of 5 average rating, 36 reviewsLuxe Suite + Spa House Retreat! Pets Welcome
Apartment in West Rogers Park
4.78 out of 5 average rating, 23 reviewsSpacious Beautiful Condo
Apartment in Chicago
5.0 out of 5 average rating, 11 reviewsLake, City, & River View Condo
Apartment in The Loop
4.8 out of 5 average rating, 10 reviewsThe Areal Oasis
Weekly apartment rentals
Apartment in Near North Side
4.89 out of 5 average rating, 378 reviewsGreat Location Studio in the Gold Coast!!
Apartment in Chicago
4.89 out of 5 average rating, 141 reviewsCharming Gold Coast One-Bedroom Near Downtown!
Apartment in Wicker Park
4.95 out of 5 average rating, 175 reviewsWicker Park/Bucktown Location
Apartment in Logan Square
4.9 out of 5 average rating, 345 reviewsSunny Logan Square Artists' home
Apartment in Chicago
4.99 out of 5 average rating, 197 reviewsExplore Lincoln Park from a Polished Apartment
Apartment in Wicker Park
4.83 out of 5 average rating, 482 reviewsRelaxed Bucktown/Wicker Park 1B Apt
Apartment in Oak Park
4.86 out of 5 average rating, 251 reviewsCosmopolitan Nest in Oak Park North Side
Apartment in West Town
4.92 out of 5 average rating, 329 reviewsBright, Modern Apartment in a Vintage Greystone
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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