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 Chicago
4.9 out of 5 average rating, 261 reviewsBright & Lofty Bucktown 1br
Apartment in Chicago
4.86 out of 5 average rating, 106 reviews⭐️⭐️Entire Unite 2-Bdr. HORNER PARK⭐️⭐️
Apartment in Chicago
4.96 out of 5 average rating, 113 reviewsComfortable, modern apartment 20 Min from Downtown
Apartment in Chicago
4.87 out of 5 average rating, 487 reviewsLogan Square Studio
Apartment in Chicago
4.93 out of 5 average rating, 383 reviewsRavenswood Guest House Annex
Apartment in Oak Park
4.85 out of 5 average rating, 536 reviewsLong stays welcome@warm&cute vintage 2BR
Apartment in Forest Park
4.93 out of 5 average rating, 593 reviewsPeaceful oasis in Forest Park
Apartment in Logan Square
4.97 out of 5 average rating, 259 reviewsLogan Square 2nd Floor Chicago Victorian
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, 206 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 Chicago
4.78 out of 5 average rating, 23 reviewsSpacious Beautiful Condo
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
Weekly apartment rentals
Apartment in Chicago
4.8 out of 5 average rating, 387 reviews'Secret Garden' Apartment in Wrigleyville
Apartment in Chicago
4.89 out of 5 average rating, 475 reviewsiKlektik House Chicago / Robin
Apartment in Irving Park
4.97 out of 5 average rating, 253 reviewsSpacious 1BR apartment in a central location
Apartment in Chicago
4.96 out of 5 average rating, 255 reviewsSunny, Cozy, Colorful Andersonville
Apartment in Chicago
4.82 out of 5 average rating, 440 reviewsLovely Andersonville Apt with Ideal Location
Apartment in Chicago
4.9 out of 5 average rating, 287 reviewsModern Logan Square Apartment, steps from train!
Apartment in Chicago
4.92 out of 5 average rating, 329 reviewsBright, Modern Apartment in a Vintage Greystone
Apartment in Chicago
4.98 out of 5 average rating, 225 reviewsUkrainian Village Garden Retreat
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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