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
Apartment in Portage Park
4.96 out of 5 average rating, 114 reviewsComfortable, modern apartment 20 Min from Downtown
Apartment in Chicago
4.96 out of 5 average rating, 380 reviewsKing Bed, Huge Spa Shower, Dining Destination
Apartment in Chicago
4.87 out of 5 average rating, 276 reviewsHistoric Old Town Flat - Minutes from Downtown!
Apartment in Chicago
4.84 out of 5 average rating, 135 reviewsPerfect Private Getaway in Perfect Pilsen
Apartment in Avondale
4.97 out of 5 average rating, 122 reviewsDesigner Avondale Attic
Apartment in Lincoln Square
4.94 out of 5 average rating, 193 reviewsSpacious, light-drenched studio-private entrance!
Apartment in Wicker Park
4.95 out of 5 average rating, 259 reviewsHeart of Bucktown
Apartment in Logan Square
4.89 out of 5 average rating, 346 reviewsSunny Logan Square Artists' home
Private apartment rentals
Apartment in West Town
4.89 out of 5 average rating, 479 reviewsiKlektik House Chicago / Robin
Apartment in Logan Square
4.87 out of 5 average rating, 488 reviewsLogan Square Studio
Apartment in Chicago
4.91 out of 5 average rating, 115 reviewsNEW Modern 2BRD apartment| 5min to McCormick Place
Apartment in Pilsen Historic District
4.87 out of 5 average rating, 339 reviewsCozy Garden Apartment in Heart of Pilsen
Apartment in Pilsen Historic District
4.85 out of 5 average rating, 239 reviewsTeeny Tiny Bohemian Lodge - Clean & Affordable
Apartment in Wicker Park
4.78 out of 5 average rating, 222 reviewsPrivate Studio Apt in the Heart of Wicker Park!
Apartment in Wicker Park
4.83 out of 5 average rating, 483 reviewsRelaxed Bucktown/Wicker Park 1B Apt
Apartment in Wicker Park
4.97 out of 5 average rating, 237 reviewsStylish First Flr. Studio. Best Location Division+Hermitage.
Apartment rentals with a hot tub
Apartment in Chicago
4.87 out of 5 average rating, 160 reviewsSkyline Serenity: Sauna, Hot Tub, Peloton, Views
Apartment in West Town
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 West Loop
4.87 out of 5 average rating, 106 reviewsCloud9 |XL Penthouse+Movie Theater+Gym |The Harper
Apartment in Logan Square
4.92 out of 5 average rating, 37 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 West Loop
5.0 out of 5 average rating, 11 reviewsSkyline Oasis: City & Lake Views
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