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
Weekly apartment rentals
Apartment in Oak Park
4.85 out of 5 average rating, 530 reviewsLong stays welcome@warm&cute vintage 2BR
Sep. 26 – Oct. 3
Apartment in Chicago
4.91 out of 5 average rating, 373 reviewsThe Grotto of Logan Square
Sep. 4 – 9
Apartment in Chicago
4.9 out of 5 average rating, 372 reviewsGreat Location Studio in the Gold Coast!!
Dec. 24 – 31
Apartment in Chicago
4.86 out of 5 average rating, 101 reviews⭐️⭐️Entire Unite 2-Bdr. HORNER PARK⭐️⭐️
Apr. 4 – 11
Apartment in Chicago
4.95 out of 5 average rating, 108 reviewsComfortable, modern apartment 20 Min from Downtown
Nov. 11 – 18
Apartment in Chicago
4.96 out of 5 average rating, 257 reviewsLogan Square 2nd Floor Chicago Victorian
Nov. 9 – 16
Apartment in Lake View
4.86 out of 5 average rating, 201 reviewsPrivate Queen Bedroom and En Suite Bath
Jul. 10 – 17
Apartment in Chicago
4.84 out of 5 average rating, 175 reviewsThe Cottage
Sep. 29 – Oct. 6
Private apartment rentals
Apartment in Logan Square
4.89 out of 5 average rating, 339 reviewsSunny Logan Square Artists' home
Feb. 10 – 17
Apartment in Oak Park
4.86 out of 5 average rating, 248 reviewsCosmopolitan Nest in Oak Park North Side
Sep. 6 – 13
Apartment in Chicago
4.92 out of 5 average rating, 491 reviews2BR Bursting w/ Character in Hip Logan Square!
Apr. 6 – 13
Apartment in Pilsen Historic District
4.85 out of 5 average rating, 234 reviewsTeeny Tiny Bohemian Lodge - Clean & Affordable
Aug. 19 – 26
Apartment in Oak Park
4.91 out of 5 average rating, 104 reviewsLovely, spacious 2bd, 1bath home w/free parking
Sep. 25 – Oct. 2
Apartment in Logan Square
4.87 out of 5 average rating, 486 reviewsLogan Square Studio
Feb. 21 – 28
Apartment in Wicker Park
4.84 out of 5 average rating, 480 reviewsRelaxed Bucktown/Wicker Park 1B Apt
Oct. 15 – 22
Apartment in Forest Park
4.93 out of 5 average rating, 585 reviewsPeaceful oasis in Forest Park
Sep. 3 – 10
Apartment rentals with a hot tub
Apartment in Chicago
4.88 out of 5 average rating, 393 reviewsCheckerboard Studio with Private Outdoor Hot Tub and Yard
Aug. 19 – 26
Apartment in Chicago
4.87 out of 5 average rating, 156 reviewsStunning Panoramic Chicago Views & Free Parking
Nov. 1 – 8
Apartment in Chicago
4.87 out of 5 average rating, 106 reviewsCloud9 |XL Penthouse+Movie Theater+Gym |The Harper
Feb. 18 – 25
Apartment in Berwyn
4.91 out of 5 average rating, 203 reviews“Dream slice of urban homesteading.”
Apr. 27 – May 4
Apartment in Chicago
4.9 out of 5 average rating, 30 reviewsLuxe Suite + Spa House Retreat! Pets Welcome
Mar. 8 – 15
Apartment in Chicago
4.94 out of 5 average rating, 18 reviewsSpacious Beautiful Condo
Oct. 19 – 26
Apartment in Chicago
5.0 out of 5 average rating, 10 reviewsLake, City, & River View Condo
Jul. 10 – 17
Apartment in Chicago
5.0 out of 5 average rating, 6 reviewsThe Downtown Oasis (2BD / 2BA)
Feb. 10 – 17
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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