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 Oak Park
4.97 out of 5 average rating, 167 reviewsChic Retreat in Historic Victorian House-Park Free
Apartment in Forest Park
5.0 out of 5 average rating, 229 reviewsLike a Treehouse!
Apartment in Chicago
4.98 out of 5 average rating, 111 reviewsHumboldt Park Loft
Apartment in Chicago
4.89 out of 5 average rating, 476 reviewsiKlektik House Chicago / Robin
Apartment in Chicago
4.83 out of 5 average rating, 215 reviewsCozy Lincoln Park Studio - Steps to Zoo!
Apartment in Chicago
4.96 out of 5 average rating, 380 reviewsKing Bed, Huge Spa Shower, Dining Destination
Apartment in Chicago
4.93 out of 5 average rating, 383 reviewsRavenswood Guest House Annex
Apartment in Chicago
4.96 out of 5 average rating, 114 reviewsComfortable, modern apartment 20 Min from Downtown
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 Berwyn
4.91 out of 5 average rating, 207 reviews“Dream slice of urban homesteading.”
Apartment in Chicago
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 Chicago
4.92 out of 5 average rating, 36 reviewsLuxe Suite + Spa House Retreat! Pets Welcome
Apartment in Streeterville
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
Apartment in Chicago
4.79 out of 5 average rating, 24 reviewsSpacious Beautiful Condo
Weekly apartment rentals
Apartment in Chicago
4.89 out of 5 average rating, 248 reviewsModern
Apartment in Forest Park
4.93 out of 5 average rating, 594 reviewsPeaceful oasis in Forest Park
Apartment in Chicago
4.89 out of 5 average rating, 346 reviewsSunny Logan Square Artists' home
Apartment in Oak Park
4.92 out of 5 average rating, 200 reviewsClean & Cozy Oak Park Vintage 1BR: Tv NFL PASS
Apartment in Chicago
4.96 out of 5 average rating, 102 reviewsCute, Clean, Cozy Apartment in Pilsen
Apartment in Chicago
4.96 out of 5 average rating, 257 reviewsSunny, Cozy, Colorful Andersonville
Apartment in Chicago
4.9 out of 5 average rating, 287 reviewsModern Logan Square Apartment, steps from train!
Apartment in Berwyn
4.87 out of 5 average rating, 147 reviewsThe Green Bungalow: Charming 1-BR apt. with patio
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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