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
Get the amount of space that is right for you
Popular amenities for Downtown Chicago apartment rentals
Weekly apartment rentals
Rental unit in Chicago
4.96 out of 5 average rating, 267 reviewsTurquoise Wonder - Clean, Cozy & Stylish Apt
Rental unit in Chicago
4.93 out of 5 average rating, 173 reviewsCharming Apt. near Wrigley/Cubs, Ravenswood/Uptown
Rental unit in Chicago
4.78 out of 5 average rating, 139 reviewsRoomy Getaway in Vibrant Center of Lincoln Park
Rental unit in Chicago
4.89 out of 5 average rating, 482 reviewsiKlektik House Chicago / Robin
Rental unit in Chicago
4.82 out of 5 average rating, 445 reviewsLovely Andersonville Apt with Ideal Location
Rental unit in Chicago
5 out of 5 average rating, 201 reviewsExplore Lincoln Park from a Polished Apartment
Rental unit in Chicago
4.95 out of 5 average rating, 117 reviewsComfortable, modern apartment 20 Min from Downtown
Rental unit in Chicago
4.89 out of 5 average rating, 351 reviewsSunny Logan Square Artists' home
Private apartment rentals
Rental unit in Chicago
4.95 out of 5 average rating, 204 reviewsFree Parking & King Bed in Desirable Norwood Park!
Rental unit in Chicago
4.85 out of 5 average rating, 243 reviewsTeeny Tiny Bohemian Lodge - Clean & Affordable
Rental unit in Oak Park
4.89 out of 5 average rating, 349 reviewsCharming Chicago-Style, Vintage, Tv NFL PASS
Rental unit in Oak Park
4.85 out of 5 average rating, 542 reviewsLong stays welcome@warm&cute vintage 2BR
Rental unit in Chicago
4.93 out of 5 average rating, 196 reviewsSpacious, light-drenched studio-private entrance!
Rental unit in Chicago
4.86 out of 5 average rating, 209 reviewsSpectacular Pilsen Studio for 2!
Rental unit in Chicago
4.78 out of 5 average rating, 223 reviewsPrivate Studio Apt in the Heart of Wicker Park!
Rental unit in Chicago
4.83 out of 5 average rating, 486 reviewsRelaxed Bucktown/Wicker Park 1B Apt
Apartment rentals with a hot tub
Rental unit in Chicago
4.88 out of 5 average rating, 402 reviewsCheckerboard Studio with Private Outdoor Hot Tub and Yard
Rental unit in Chicago
4.87 out of 5 average rating, 166 reviewsSkyline Serenity: Sauna, Hot Tub, Peloton, Views
Rental unit in Berwyn
4.91 out of 5 average rating, 213 reviews“Dream slice of urban homesteading.”
Rental unit in Chicago
4.92 out of 5 average rating, 38 reviewsLuxe Suite + Spa House Retreat! Pets Welcome
Rental unit in Chicago
5 out of 5 average rating, 12 reviewsLake, City, & River View Condo
Rental unit in Chicago
4.83 out of 5 average rating, 30 reviewsThe Professional's Playground
Rental unit in Chicago
4.81 out of 5 average rating, 27 reviewsSpacious Beautiful Condo
Rental unit in Chicago
5 out of 5 average rating, 13 reviewsSkyline Oasis: City & Lake Views
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