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 Lincoln Park
4.78 out of 5 average rating, 139 reviewsRoomy Getaway in Vibrant Center of Lincoln Park
Apartment in Humboldt Park
4.98 out of 5 average rating, 111 reviewsHumboldt Park Loft
Apartment in Chicago
4.84 out of 5 average rating, 178 reviewsThe Cottage
Apartment in Forest Park
4.93 out of 5 average rating, 603 reviewsPeaceful oasis in Forest Park
Apartment in Chicago
4.93 out of 5 average rating, 173 reviewsCharming Apt. near Wrigley/Cubs, Ravenswood/Uptown
Apartment in Forest Park
5.0 out of 5 average rating, 232 reviewsLike a Treehouse!
Apartment in Chicago
4.87 out of 5 average rating, 489 reviewsLogan Square Studio
Apartment in Chicago
4.98 out of 5 average rating, 203 reviewsSpacious 2BR on Quiet St - Free Park/Late Checkout
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 West Loop
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, 29 reviewsThe Professional's Playground
Apartment in Chicago
4.8 out of 5 average rating, 25 reviewsSpacious Beautiful Condo
Weekly apartment rentals
Apartment in Oak Park
4.86 out of 5 average rating, 540 reviewsLong stays welcome@warm&cute vintage 2BR
Apartment in Chicago
4.89 out of 5 average rating, 351 reviewsSunny Logan Square Artists' home
Apartment in Chicago
4.86 out of 5 average rating, 107 reviews⭐️⭐️Entire Unite 2-Bdr. HORNER PARK⭐️⭐️
Apartment in Chicago
4.89 out of 5 average rating, 250 reviewsModern
Apartment in Chicago
4.98 out of 5 average rating, 139 reviewsModern Apt with style & comfort in Pilsen Chicago
Apartment in Logan Square
4.91 out of 5 average rating, 380 reviewsThe Grotto of Logan Square
Apartment in Chicago
5.0 out of 5 average rating, 200 reviewsExplore Lincoln Park from a Polished Apartment
Apartment in Logan Square
4.97 out of 5 average rating, 260 reviewsLogan Square 2nd Floor Chicago Victorian
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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