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
4.89 out of 5 average rating, 107 reviewsLAKESIDE PIED `A TERRE STEPS TO BEACH
Apartment in Cicero
4.98 out of 5 average rating, 208 reviewsCOZY 2Bdr Apt near MDW, Dwtn, United Ctr, Sox, Hwy
Apartment in Chicago
4.89 out of 5 average rating, 476 reviewsiKlektik House Chicago / Robin
Apartment in Lincoln Square
4.94 out of 5 average rating, 193 reviewsSpacious, light-drenched studio-private entrance!
Apartment in Lincoln Park
4.83 out of 5 average rating, 215 reviewsCozy Lincoln Park Studio - Steps to Zoo!
Apartment in Logan Square
4.87 out of 5 average rating, 488 reviewsLogan Square Studio
Apartment in Humboldt Park
4.98 out of 5 average rating, 111 reviewsHumboldt Park Loft
Apartment in Chicago
4.89 out of 5 average rating, 346 reviewsSunny Logan Square Artists' home
Private apartment rentals
Apartment in Uptown
4.96 out of 5 average rating, 268 reviewsCozy loft in Chicago's Uptown
Apartment in Irving Park
4.92 out of 5 average rating, 599 reviewsExplore Chicago from an Urban Sanctuary with Free Parking
Apartment in Chicago
4.82 out of 5 average rating, 277 reviews*Entire City Apartment 1 block to Train Park Free
Apartment in Roscoe Village
4.88 out of 5 average rating, 178 reviews★Bright & Bold 1BR in Roscoe Village + Fireplace★
Apartment in Logan Square
4.9 out of 5 average rating, 287 reviewsModern Logan Square Apartment, steps from train!
Apartment in Lincoln Park
4.79 out of 5 average rating, 177 reviewsPerfect 1br In Lincoln Park - Steps to Depaul!
Apartment in Chicago
4.85 out of 5 average rating, 168 reviewsYour brand new Chicago suite (unit 1F)
Apartment in Oak Park
4.89 out of 5 average rating, 341 reviewsCharming Chicago-Style, Vintage, Tv NFL PASS
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, 160 reviewsSkyline Serenity: Sauna, Hot Tub, Peloton, Views
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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