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 Logan Square
4.92 out of 5 average rating, 491 reviews2BR Bursting w/ Character in Hip Logan Square!
Apr 8 – 15
Apartment in Uptown
4.96 out of 5 average rating, 266 reviewsCozy loft in Chicago's Uptown
Oct 19 – 26
Apartment in Pilsen Historic District
4.89 out of 5 average rating, 202 reviewsSpectacular Pilsen Studio for 2!
Dec 8 – 15
Apartment in Lincoln Square
4.81 out of 5 average rating, 124 reviewsTranquil & Airy 1BR Apt in Lincoln Square
May 7 – 14
Apartment in Chicago
4.86 out of 5 average rating, 101 reviews⭐️⭐️Entire Unite 2-Bdr. HORNER PARK⭐️⭐️
Apr 4 – 11
Apartment in Chicago
4.97 out of 5 average rating, 457 reviewsFully Furnished Apartment Wicker Park Free Parking
Apartment in Lincoln Square
4.96 out of 5 average rating, 323 reviewsBright family-friendly Lincoln Square 2-bed 1-bath
Jan 4 – 11
Apartment in Chicago
4.96 out of 5 average rating, 238 reviewsRoscoe Village One Bed Lux Apartment Near Wrigley
Nov 18 – 25
Private apartment rentals
Apartment in Irving Park
4.97 out of 5 average rating, 251 reviewsSpacious 1BR apartment in a central location
Oct 1 – 8
Apartment in Wicker Park
4.97 out of 5 average rating, 236 reviewsStylish First Flr. Studio. Best Location Division+Hermitage.
Jan 26 – Feb 2
Apartment in Irving Park
4.92 out of 5 average rating, 593 reviewsExplore Chicago from an Urban Sanctuary with Free Parking
Dec 1 – 8
Apartment in Logan Square
4.89 out of 5 average rating, 339 reviewsSunny Logan Square Artists' home
Apr 21 – 28
Apartment in West Town
4.92 out of 5 average rating, 326 reviewsBright, Modern Apartment in a Vintage Greystone
Nov 10 – 17
Apartment in Wicker Park
4.95 out of 5 average rating, 172 reviewsWicker Park/Bucktown Location
Apartment in Oak Park
4.85 out of 5 average rating, 531 reviewsLong stays welcome@warm&cute vintage 2BR
Sep 29 – Oct 6
Apartment in Chicago
4.82 out of 5 average rating, 436 reviewsLovely Andersonville Apt with Ideal Location
Dec 28 – Jan 4
Apartment rentals with a hot tub
Apartment in Chicago
4.88 out of 5 average rating, 394 reviewsCheckerboard Studio with Private Outdoor Hot Tub and Yard
Jun 27 – Jul 4
Apartment in Chicago
4.87 out of 5 average rating, 156 reviewsStunning Panoramic Chicago Views & Free Parking
Mar 27 – Apr 3
Apartment in Berwyn
4.91 out of 5 average rating, 203 reviews“Dream slice of urban homesteading.”
Oct 22 – 29
Apartment in Chicago
4.9 out of 5 average rating, 31 reviewsLuxe Suite + Spa House Retreat! Pets Welcome
Mar 19 – 26
Apartment in Streeterville
5.0 out of 5 average rating, 10 reviewsLake, City, & River View Condo
Jul 19 – 26
Apartment in Chicago
4.95 out of 5 average rating, 19 reviewsSpacious Beautiful Condo
Oct 17 – 24
Apartment in Chicago
5.0 out of 5 average rating, 6 reviewsThe Downtown Oasis (2BD / 2BA)
Feb 10 – 17
Apartment in Chicago
5.0 out of 5 average rating, 20 reviewsRiver View Cityscape Condo
May 6 – 13
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