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 Chicago
4.89 out of 5 average rating, 176 reviewsHistoric Chicago neighborhood flat
Dec 13 – 20
Apartment in Chicago
4.98 out of 5 average rating, 128 reviewsModern Apt with style & comfort in Pilsen Chicago
Jul 9 – 16
Apartment in Chicago
4.98 out of 5 average rating, 218 reviewsUkrainian Village Garden Retreat
Nov 20 – 27
Apartment in Chicago
4.82 out of 5 average rating, 435 reviewsLovely Andersonville Apt with Ideal Location
Dec 21 – 28
Apartment in Chicago
4.9 out of 5 average rating, 283 reviewsModern Logan Square Apartment, steps from train!
Nov 17 – 24
Apartment in Chicago
4.84 out of 5 average rating, 175 reviewsThe Cottage
Sep 12 – 19
Apartment in Forest Park
5.0 out of 5 average rating, 219 reviewsLike a Treehouse!
Oct 4 – 11
Apartment in Chicago
4.86 out of 5 average rating, 101 reviews⭐️⭐️Entire Unite 2-Bdr. HORNER PARK⭐️⭐️
Apr 19 – 26
Weekly apartment rentals
Apartment in Chicago
4.79 out of 5 average rating, 172 reviewsPerfect 1br In Lincoln Park - Steps to Depaul!
Jan 4 – 11
Apartment in Oak Park
4.86 out of 5 average rating, 247 reviewsCosmopolitan Nest in Oak Park North Side
Oct 3 – 10
Apartment in Oak Park
4.84 out of 5 average rating, 494 reviewsSunny Jumbo Studio NO cleaning fee!
Mar 10 – 17
Apartment in Oak Park
4.88 out of 5 average rating, 128 reviewsA Little Slice of Heaven in Oak Park, IL
Feb 13 – 20
Apartment in Oak Park
4.92 out of 5 average rating, 196 reviewsClean & Cozy Oak Park Vintage 1BR: Tv NFL PASS
Jan 3 – 10
Apartment in Chicago
4.89 out of 5 average rating, 140 reviewsCharming Gold Coast One-Bedroom Near Downtown!
Mar 6 – 13
Apartment in Oak Park
4.97 out of 5 average rating, 163 reviewsChic Retreat in Historic Victorian House-Park Free
Jan 28 – Feb 4
Apartment in Near North Side
4.8 out of 5 average rating, 492 reviewsGreat Location!!-12
Dec 25 – Jan 1
Private apartment rentals
Apartment in Chicago
4.96 out of 5 average rating, 483 reviewsStunning Retro Apartment in Andersonville
Dec 2 – 9
Apartment in Pilsen Historic District
4.85 out of 5 average rating, 233 reviewsTeeny Tiny Bohemian Lodge - Clean & Affordable
Aug 15 – 22
Apartment in Chicago
4.87 out of 5 average rating, 123 reviewsRemodeled Boho Chic 1 Bed in Hip Logan Square
Jun 11 – 18
Apartment in Irving Park
4.92 out of 5 average rating, 591 reviewsExplore Chicago from an Urban Sanctuary with Free Parking
Sep 6 – 13
Apartment in Wicker Park
4.78 out of 5 average rating, 217 reviewsPrivate Studio Apt in the Heart of Wicker Park!
Jan 19 – 26
Apartment in Forest Park
4.88 out of 5 average rating, 16 reviewsCity-Accessible Basement Retreat
Nov 13 – 20
Apartment in Norwood Park
5.0 out of 5 average rating, 6 reviews1BD Apt near O'Hare/Rosemont Allstate Arena
Jun 9 – 16
Apartment in Chicago
4.96 out of 5 average rating, 23 reviewsLincoln Square Oasis - Bright, clean studio
Nov 22 – 29
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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