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 Forest Park
4.93 out of 5 average rating, 584 reviewsPeaceful oasis in Forest Park
Aug. 24 – 31
Apartment in West Town
4.89 out of 5 average rating, 473 reviewsiKlektik House Chicago / Robin
Dec. 10 – 17
Apartment in Chicago
4.92 out of 5 average rating, 185 reviewsTaj Ma-small at Wrigley
Mar. 1 – 8
Apartment in Oak Park
4.85 out of 5 average rating, 527 reviewsLong stays welcome@warm&cute vintage 2BR
Oct. 15 – 22
Apartment in Logan Square
4.93 out of 5 average rating, 207 reviewsCozy Private Coach House
Jul. 25 – Aug. 1
Apartment in Irving Park
4.89 out of 5 average rating, 176 reviewsHistoric Chicago neighborhood flat
Nov. 10 – 17
Apartment in Logan Square
4.87 out of 5 average rating, 484 reviewsLogan Square Studio
Jan. 2 – 9
Apartment in Lake View
4.86 out of 5 average rating, 201 reviewsPrivate Queen Bedroom and En Suite Bath
Jul. 3 – 10
Private apartment rentals
Apartment in Chicago
4.86 out of 5 average rating, 101 reviews⭐️⭐️Entire Unite 2-Bdr. HORNER PARK⭐️⭐️
Apr. 13 – 20
Apartment in Chicago
4.84 out of 5 average rating, 175 reviewsThe Cottage
Oct. 3 – 10
Apartment in Andersonville
4.98 out of 5 average rating, 249 reviewsAndersonville Cozy 1 bedroom basement suite
Nov. 26 – Dec. 3
Apartment in Logan Square
4.9 out of 5 average rating, 283 reviewsModern Logan Square Apartment, steps from train!
Jan. 1 – 8
Apartment in Chicago
4.84 out of 5 average rating, 130 reviewsPerfect Private Getaway in Perfect Pilsen
Aug. 6 – 13
Apartment in Wicker Park
4.84 out of 5 average rating, 479 reviewsRelaxed Bucktown/Wicker Park 1B Apt
Oct. 14 – 21
Apartment in Chicago
4.95 out of 5 average rating, 106 reviewsComfortable, modern apartment 20 Min from Downtown
Mar. 5 – 12
Apartment in Chicago
4.79 out of 5 average rating, 172 reviewsPerfect 1br In Lincoln Park - Steps to Depaul!
Jan. 4 – 11
Apartment rentals with a hot tub
Apartment in Berwyn
4.91 out of 5 average rating, 201 reviews“Dream slice of urban homesteading.”
Feb. 9 – 16
Apartment in Chicago
4.88 out of 5 average rating, 393 reviewsCheckerboard Studio with Private Outdoor Hot Tub and Yard
Jul. 16 – 23
Apartment in Chicago
4.86 out of 5 average rating, 154 reviewsStunning Panoramic Chicago Views & Free Parking
Nov. 2 – 9
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 Chicago
4.93 out of 5 average rating, 28 reviewsLuxe Suite + Spa House Retreat! Pets Welcome
Mar. 10 – 17
Apartment in Chicago
5.0 out of 5 average rating, 16 reviewsSpacious Beautiful Condo
Sep. 10 – 17
Apartment in Streeterville
5.0 out of 5 average rating, 9 reviewsLake, City, & River View Condo
May 6 – 13
Apartment in Chicago
4.79 out of 5 average rating, 24 reviewsThe Professional's Playground
Jan. 2 – 9
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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