Apartment vacation rentals in Downtown Chicago
Find and book unique apartments on Airbnb
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 West Town
4.89 out of 5 average rating, 474 reviewsiKlektik House Chicago / Robin
Apartment in Chicago
4.84 out of 5 average rating, 132 reviewsPerfect Private Getaway in Perfect Pilsen
Apartment in Lincoln Square
4.94 out of 5 average rating, 193 reviewsSpacious, light-drenched studio-private entrance!
Apartment in Near West Side
4.82 out of 5 average rating, 275 reviews*Entire City Apartment 1 block to Train Park Free
Apartment in Pilsen Historic District
4.85 out of 5 average rating, 237 reviewsTeeny Tiny Bohemian Lodge - Clean & Affordable
Apartment in Lincoln Park
4.83 out of 5 average rating, 213 reviewsCozy Lincoln Park Studio - Steps to Zoo!
Apartment in Pilsen Historic District
4.89 out of 5 average rating, 245 reviewsModern
Apartment in Chicago
4.82 out of 5 average rating, 440 reviewsLovely Andersonville Apt with Ideal Location
Private apartment rentals
Apartment in Chicago
4.98 out of 5 average rating, 133 reviewsModern Apt with style & comfort in Pilsen Chicago
Apartment in Irving Park
4.92 out of 5 average rating, 596 reviewsExplore Chicago from an Urban Sanctuary with Free Parking
Apartment in Chicago
4.85 out of 5 average rating, 164 reviewsYour brand new Chicago suite (unit 1F)
Apartment in Chicago
4.91 out of 5 average rating, 112 reviewsNEW Modern 2BRD apartment| 5min to McCormick Place
Apartment in Pilsen Historic District
4.88 out of 5 average rating, 204 reviewsSpectacular Pilsen Studio for 2!
Apartment in Chicago
4.99 out of 5 average rating, 197 reviewsExplore Lincoln Park from a Polished Apartment
Apartment in Bridgeport
4.98 out of 5 average rating, 172 reviewsBridgeport Garden Apartment
Apartment in Chicago
4.96 out of 5 average rating, 379 reviewsKing Bed, Huge Spa Shower, Dining Destination
Apartment rentals with a hot tub
Apartment in West Town
4.88 out of 5 average rating, 398 reviewsCheckerboard Studio with Private Outdoor Hot Tub and Yard
Apartment in Near South Side
4.87 out of 5 average rating, 159 reviewsSkyline Serenity: Sauna, Hot Tub, Peloton, Views
Apartment in Berwyn
4.91 out of 5 average rating, 205 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, 36 reviewsLuxe Suite + Spa House Retreat! Pets Welcome
Apartment in The Loop
4.8 out of 5 average rating, 10 reviewsThe Areal Oasis
Apartment in West Rogers Park
4.82 out of 5 average rating, 22 reviewsSpacious Beautiful Condo
Apartment in Magnificent Mile
4.87 out of 5 average rating, 77 reviews4Br Gold Coast Duplex w Jacuzzi in the Bedroom!
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