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 Chicago
4.96 out of 5 average rating, 237 reviewsRoscoe Village One Bed Lux Apartment Near Wrigley
Nov 3 – 10
Apartment in Chicago
4.97 out of 5 average rating, 455 reviewsFully Furnished Apartment Wicker Park Free Parking
Apartment in Irving Park
4.86 out of 5 average rating, 101 reviews⭐️⭐️Entire Unite 2-Bdr. HORNER PARK⭐️⭐️
Apr 13 – 20
Apartment in Oak Park
4.89 out of 5 average rating, 333 reviewsCharming Chicago-Style, Vintage, Tv NFL PASS
Jan 17 – 24
Apartment in Irving Park
4.92 out of 5 average rating, 591 reviewsExplore Chicago from an Urban Sanctuary with Free Parking
Nov 2 – 9
Apartment in Wicker Park
4.95 out of 5 average rating, 172 reviewsWicker Park/Bucktown Location
Jul 19 – 24
Apartment in Logan Square
4.91 out of 5 average rating, 371 reviewsThe Grotto of Logan Square
Oct 1 – 6
Apartment in Logan Square
4.87 out of 5 average rating, 484 reviewsLogan Square Studio
Feb 6 – 13
Private apartment rentals
Apartment in Chicago
4.87 out of 5 average rating, 271 reviewsHistoric Old Town Flat - Minutes from Downtown!
Jan 28 – Feb 4
Apartment in Logan Square
4.89 out of 5 average rating, 339 reviewsSunny Logan Square Artists' home
Dec 1 – 8
Apartment in Lincoln Square
4.8 out of 5 average rating, 123 reviewsTranquil & Airy 1BR Apt in Lincoln Square
May 10 – 17
Apartment in Chicago
4.93 out of 5 average rating, 207 reviewsCozy Private Coach House
Oct 4 – 11
Apartment in Logan Square
4.81 out of 5 average rating, 105 reviewsWelcome Chez Moi
Aug 13 – 20
Apartment in Andersonville
4.82 out of 5 average rating, 436 reviewsLovely Andersonville Apt with Ideal Location
Jan 12 – 19
Apartment in Chicago
4.84 out of 5 average rating, 130 reviewsPerfect Private Getaway in Perfect Pilsen
Oct 5 – 12
Apartment in Wicker Park
4.78 out of 5 average rating, 217 reviewsPrivate Studio Apt in the Heart of Wicker Park!
Nov 22 – 29
Apartment rentals with a hot tub
Apartment in West Town
4.88 out of 5 average rating, 393 reviewsCheckerboard Studio with Private Outdoor Hot Tub and Yard
Oct 9 – 16
Apartment in Chicago
4.86 out of 5 average rating, 155 reviewsStunning Panoramic Chicago Views & Free Parking
Oct 4 – 11
Apartment in Berwyn
4.91 out of 5 average rating, 202 reviews“Dream slice of urban homesteading.”
Feb 10 – 17
Apartment in West Loop
4.87 out of 5 average rating, 106 reviewsCloud9 |XL Penthouse+Movie Theater+Gym |The Harper
May 15 – 22
Apartment in Logan Square
4.9 out of 5 average rating, 29 reviewsLuxe Suite + Spa House Retreat! Pets Welcome
Nov 13 – 20
Apartment in Chicago
5.0 out of 5 average rating, 9 reviewsLake, City, & River View Condo
May 6 – 13
Apartment in West Rogers Park
5.0 out of 5 average rating, 16 reviewsSpacious Beautiful Condo
Oct 14 – 21
Apartment in The Loop
4.79 out of 5 average rating, 24 reviewsThe Professional's Playground
Jan 2 – 9
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