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
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Popular amenities for Chicago apartment rentals
Weekly apartment rentals
Apartment in Chicago
4.87 out of 5 average rating, 104 reviews⭐️⭐️Entire Unite 2-Bdr. HORNER PARK⭐️⭐️
Apartment in Chicago
4.93 out of 5 average rating, 382 reviewsRavenswood Guest House Annex
Apartment in Logan Square
4.91 out of 5 average rating, 374 reviewsThe Grotto of Logan Square
Apartment in Gold Coast
4.89 out of 5 average rating, 140 reviewsCharming Gold Coast One-Bedroom Near Downtown!
Apartment in Chicago
4.93 out of 5 average rating, 191 reviewsQuirky Designer Apartment - Steps from Wrigley!
Apartment in Irving Park
4.97 out of 5 average rating, 252 reviewsSpacious 1BR apartment in a central location
Apartment in Chicago
4.96 out of 5 average rating, 166 reviews2BR Centrally Located in Cozy Hip Logan Square
Apartment in Forest Park
4.98 out of 5 average rating, 288 reviewsWalk to Oak Park from Our Sunny Turn of the Century Apt
Private apartment rentals
Apartment in West Town
4.89 out of 5 average rating, 474 reviewsiKlektik House Chicago / Robin
Apartment in Oak Park
4.85 out of 5 average rating, 533 reviewsLong stays welcome@warm&cute vintage 2BR
Apartment in Wicker Park
4.95 out of 5 average rating, 256 reviewsHeart of Bucktown
Apartment in Chicago
4.93 out of 5 average rating, 170 reviewsCharming Apt. near Wrigley/Cubs, Ravenswood/Uptown
Apartment in Chicago
4.84 out of 5 average rating, 176 reviewsThe Cottage
Apartment in Forest Park
4.93 out of 5 average rating, 589 reviewsPeaceful oasis in Forest Park
Apartment in Logan Square
4.9 out of 5 average rating, 285 reviewsModern Logan Square Apartment, steps from train!
Apartment in Chicago
4.86 out of 5 average rating, 326 reviewsThe Avondale Garden Unit
Apartment rentals with a hot tub
Apartment in Chicago
4.88 out of 5 average rating, 398 reviewsCheckerboard Studio with Private Outdoor Hot Tub and Yard
Apartment in Near South Side
4.87 out of 5 average rating, 159 reviewsSkyline Serenity: Sauna, Hot Tub, Peloton, Views
Apartment in Berwyn
4.91 out of 5 average rating, 205 reviews“Dream slice of urban homesteading.”
Apartment in West Loop
4.87 out of 5 average rating, 106 reviewsCloud9 |XL Penthouse+Movie Theater+Gym |The Harper
Apartment in Chicago
4.91 out of 5 average rating, 34 reviewsLuxe Suite + Spa House Retreat! Pets Welcome
Apartment in Chicago
4.82 out of 5 average rating, 22 reviewsSpacious Beautiful Condo
Apartment in The Loop
4.8 out of 5 average rating, 10 reviewsThe Areal Oasis
Apartment in Chicago
5.0 out of 5 average rating, 29 reviewsBelmont Pleasures - hot tub / arcade gaming room
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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