Apartment vacation rentals in Chicago
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Top-rated apartment rentals in 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 Chicago apartment rentals
Apartment rentals with air conditioning
Apartment in Andersonville
4.98 out of 5 average rating, 251 reviewsAndersonville Cozy 1 bedroom basement suite
Jan 1 – 8
Apartment in Chicago
4.82 out of 5 average rating, 440 reviewsLovely Andersonville Apt with Ideal Location
Jan 20 – 27
Apartment in Lake View
4.86 out of 5 average rating, 202 reviewsPrivate Queen Bedroom and En Suite Bath
Jul 14 – 21
Apartment in Logan Square
4.97 out of 5 average rating, 258 reviewsLogan Square 2nd Floor Chicago Victorian
Nov 28 – Dec 5
Apartment in Chicago
4.83 out of 5 average rating, 564 reviewsGreat Location! Gold Coast! 07
Feb 10 – 17
Apartment in Chicago
4.95 out of 5 average rating, 109 reviewsComfortable, modern apartment 20 Min from Downtown
Apr 25 – May 2
Apartment in Forest Park
5.0 out of 5 average rating, 223 reviewsLike a Treehouse!
Sep 27 – Oct 4
Apartment in Chicago
4.98 out of 5 average rating, 171 reviewsBridgeport Garden Apartment
Sep 16 – 23
Weekly apartment rentals
Apartment in Oak Park
4.86 out of 5 average rating, 248 reviewsCosmopolitan Nest in Oak Park North Side
Oct 26 – Nov 2
Apartment in Chicago
4.8 out of 5 average rating, 385 reviews'Secret Garden' Apartment in Wrigleyville
Sep 9 – 16
Apartment in Logan Square
4.91 out of 5 average rating, 373 reviewsThe Grotto of Logan Square
Oct 18 – 23
Apartment in Chicago
4.93 out of 5 average rating, 208 reviewsCozy Private Coach House
Sep 16 – 23
Apartment in Chicago
4.98 out of 5 average rating, 132 reviewsModern Apt with style & comfort in Pilsen Chicago
Jul 23 – 30
Apartment in Chicago
4.96 out of 5 average rating, 254 reviewsSunny, Cozy, Colorful Andersonville
Oct 3 – 10
Apartment in Logan Square
4.9 out of 5 average rating, 283 reviewsModern Logan Square Apartment, steps from train!
Sep 29 – Oct 6
Apartment in Forest Park
4.92 out of 5 average rating, 112 reviewsVillage Cottage - Forest Park Studio Pets 72142F
May 9 – 16
Private apartment rentals
Apartment in Chicago
4.86 out of 5 average rating, 235 reviewsTeeny Tiny Bohemian Lodge - Clean & Affordable
Oct 2 – 9
Apartment in Chicago
4.79 out of 5 average rating, 107 reviewsBienvenu Chez Moi
Oct 22 – 29
Apartment in Park Ridge
4.79 out of 5 average rating, 322 reviewsModern Garden apartment (WHOLE UNIT)
Aug 21 – 28
Apartment in Chicago
4.82 out of 5 average rating, 273 reviews*Entire City Apartment 1 block to Train Park Free
Nov 4 – 11
Apartment in Chicago
4.93 out of 5 average rating, 382 reviewsRavenswood Guest House Annex
Jan 4 – 11
Apartment in Chicago
4.96 out of 5 average rating, 376 reviewsKing Bed, Huge Spa Shower, Dining Destination
Jan 5 – 12
Apartment in Oak Park
4.97 out of 5 average rating, 165 reviewsChic Retreat in Historic Victorian House-Park Free
Mar 1 – 8
Apartment in Chicago
4.8 out of 5 average rating, 5 reviewsLovely Lake Side Apartment
Oct 14 – 21
Quick stats about apartment rentals in Chicago
Total rentals
5.9K properties
Rentals with dedicated workspaces
3.8K properties have a dedicated workspace
Rentals with a pool
750 properties have a pool
Pet-friendly rentals
2K properties allow pets
Family-friendly rentals
2.7K properties are a good fit for families
Total number of reviews
253K reviews
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