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 Irving Park
4.86 out of 5 average rating, 106 reviews⭐️⭐️Entire Unite 2-Bdr. HORNER PARK⭐️⭐️
Apartment in Uptown
4.96 out of 5 average rating, 268 reviewsCozy loft in Chicago's Uptown
Apartment in Pilsen Historic District
4.89 out of 5 average rating, 247 reviewsModern
Apartment in Chicago
4.95 out of 5 average rating, 244 reviewsRoscoe Village One Bed Lux Apartment Near Wrigley
Apartment in Chicago
4.96 out of 5 average rating, 380 reviewsKing Bed, Huge Spa Shower, Dining Destination
Apartment in Chicago
4.84 out of 5 average rating, 132 reviewsPerfect Private Getaway in Perfect Pilsen
Apartment in Logan Square
4.9 out of 5 average rating, 345 reviewsSunny Logan Square Artists' home
Apartment in Lake View
4.93 out of 5 average rating, 171 reviewsCharming Apt. near Wrigley/Cubs, Ravenswood/Uptown
Private apartment rentals
Apartment in Wicker Park
4.95 out of 5 average rating, 175 reviewsWicker Park/Bucktown Location
Apartment in Pilsen Historic District
4.85 out of 5 average rating, 238 reviewsTeeny Tiny Bohemian Lodge - Clean & Affordable
Apartment in Portage Park
4.96 out of 5 average rating, 113 reviewsComfortable, modern apartment 20 Min from Downtown
Apartment in Near West Side
4.82 out of 5 average rating, 277 reviews*Entire City Apartment 1 block to Train Park Free
Apartment in Lincoln Square
4.94 out of 5 average rating, 193 reviewsSpacious, light-drenched studio-private entrance!
Apartment in Wicker Park
4.83 out of 5 average rating, 482 reviewsRelaxed Bucktown/Wicker Park 1B Apt
Apartment in Logan Square
4.8 out of 5 average rating, 111 reviewsWelcome Chez Moi
Apartment in Lake View
4.85 out of 5 average rating, 445 reviewsSleek and cool garden loft in East Lakeview
Apartment rentals with a hot tub
Apartment in Near South Side
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, 206 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 Streeterville
5.0 out of 5 average rating, 11 reviewsLake, City, & River View Condo
Apartment in West Rogers Park
4.78 out of 5 average rating, 23 reviewsSpacious Beautiful Condo
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