Apartment vacation rentals in Downtown Chicago
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Top-rated apartment rentals in Downtown 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 Downtown Chicago apartment rentals
Weekly apartment rentals
Apartment in Chicago
4.96 out of 5 average rating, 246 reviewsRoscoe Village One Bed Lux Apartment Near Wrigley
Apartment in Chicago
4.89 out of 5 average rating, 249 reviewsModern
Apartment in Chicago
4.95 out of 5 average rating, 115 reviewsComfortable, modern apartment 20 Min from Downtown
Apartment in Chicago
4.77 out of 5 average rating, 133 reviewsChic & Fully Furnished Studio Apt with Laundry
Apartment in Chicago
4.89 out of 5 average rating, 347 reviewsSunny Logan Square Artists' home
Apartment in Chicago
4.82 out of 5 average rating, 442 reviewsLovely Andersonville Apt with Ideal Location
Apartment in Lincoln Square
4.94 out of 5 average rating, 193 reviewsSpacious, light-drenched studio-private entrance!
Apartment in Chicago
4.96 out of 5 average rating, 382 reviewsKing Bed, Huge Spa Shower, Dining Destination
Private apartment rentals
Apartment in Oak Park
4.86 out of 5 average rating, 538 reviewsLong stays welcome@warm&cute vintage 2BR
Apartment in Chicago
4.85 out of 5 average rating, 168 reviewsYour brand new Chicago suite (unit 1F)
Apartment in Forest Park
4.88 out of 5 average rating, 103 reviewsHome in Forest Park upstairs.
Apartment in Oak Park
4.89 out of 5 average rating, 344 reviewsCharming Chicago-Style, Vintage, Tv NFL PASS
Apartment in Chicago
4.85 out of 5 average rating, 240 reviewsTeeny Tiny Bohemian Lodge - Clean & Affordable
Apartment in Logan Square
4.83 out of 5 average rating, 484 reviewsRelaxed Bucktown/Wicker Park 1B Apt
Apartment in Chicago
4.97 out of 5 average rating, 238 reviewsStylish First Flr. Studio. Best Location Division+Hermitage.
Apartment in Chicago
4.98 out of 5 average rating, 364 reviewsUnwind in Style Steps from the Magnificent Mile
Apartment rentals with a hot tub
Apartment in Near South Side
4.87 out of 5 average rating, 163 reviewsSkyline Serenity: Sauna, Hot Tub, Peloton, Views
Apartment in Chicago
4.88 out of 5 average rating, 399 reviewsCheckerboard Studio with Private Outdoor Hot Tub and Yard
Apartment in Berwyn
4.91 out of 5 average rating, 208 reviews“Dream slice of urban homesteading.”
Apartment in West Loop
4.87 out of 5 average rating, 107 reviewsCloud9 |XL Penthouse+Movie Theater+Gym |The Harper
Apartment in Chicago
4.92 out of 5 average rating, 37 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 The Loop
4.8 out of 5 average rating, 10 reviewsThe Areal Oasis
Apartment in West Loop
5.0 out of 5 average rating, 11 reviewsSkyline Oasis: City & Lake Views
Destinations to explore
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- Family travel hub Tips and inspiration
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