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
5.0 out of 5 average rating, 222 reviewsLike a Treehouse!
Sep. 26 – Oct. 3
Apartment in Lincoln Square
4.81 out of 5 average rating, 125 reviewsTranquil & Airy 1BR Apt in Lincoln Square
May 8 – 15
Apartment in Chicago
4.95 out of 5 average rating, 109 reviewsComfortable, modern apartment 20 Min from Downtown
Mar. 8 – 15
Apartment in Chicago
4.9 out of 5 average rating, 283 reviewsModern Logan Square Apartment, steps from train!
Apr. 19 – 26
Apartment in Chicago
4.93 out of 5 average rating, 382 reviewsRavenswood Guest House Annex
Apr. 20 – 27
Apartment in Oak Park
4.86 out of 5 average rating, 248 reviewsCosmopolitan Nest in Oak Park North Side
Oct. 23 – 30
Apartment in Chicago
4.83 out of 5 average rating, 564 reviewsGreat Location! Gold Coast! 07
Dec. 9 – 16
Apartment in Irving Park
4.97 out of 5 average rating, 251 reviewsSpacious 1BR apartment in a central location
Oct. 1 – 8
Private apartment rentals
Apartment in Oak Park
4.97 out of 5 average rating, 164 reviewsChic Retreat in Historic Victorian House-Park Free
Jan. 17 – 24
Apartment in Chicago
4.89 out of 5 average rating, 473 reviewsiKlektik House Chicago / Robin
Sep. 22 – 29
Apartment in Forest Park
4.93 out of 5 average rating, 585 reviewsPeaceful oasis in Forest Park
Sep. 3 – 10
Apartment in Andersonville
4.82 out of 5 average rating, 437 reviewsLovely Andersonville Apt with Ideal Location
Nov. 8 – 15
Apartment in Near West Side
4.81 out of 5 average rating, 270 reviewsThe Banksy-Greystone Rooftop Firepit United Center
Apartment in Chicago
4.89 out of 5 average rating, 140 reviewsCharming Gold Coast One-Bedroom Near Downtown!
Mar. 4 – 11
Apartment in Wicker Park
4.95 out of 5 average rating, 172 reviewsWicker Park/Bucktown Location
Apartment in Chicago
4.98 out of 5 average rating, 131 reviewsModern Apt with style & comfort in Pilsen Chicago
Jul. 26 – Aug. 2
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
Jul. 10 – 17
Apartment in Berwyn
4.91 out of 5 average rating, 203 reviews“Dream slice of urban homesteading.”
Oct. 3 – 10
Apartment in Near South Side
4.87 out of 5 average rating, 156 reviewsStunning Panoramic Chicago Views & Free Parking
Nov. 15 – 22
Apartment in West Loop
4.87 out of 5 average rating, 106 reviewsCloud9 |XL Penthouse+Movie Theater+Gym |The Harper
Apr. 8 – 15
Apartment in Chicago
4.91 out of 5 average rating, 32 reviewsLuxe Suite + Spa House Retreat! Pets Welcome
Nov. 7 – 14
Apartment in Chicago
4.9 out of 5 average rating, 20 reviewsSpacious Beautiful Condo
Oct. 23 – 30
Apartment in Chicago
5.0 out of 5 average rating, 7 reviewsThe Downtown Oasis (2BD / 2BA)
Feb. 10 – 17
Apartment in Belmont Cragin
5.0 out of 5 average rating, 26 reviewsBelmont Pleasures - hot tub / arcade gaming room
Feb. 17 – 24
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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