Apartment vacation rentals in Woodlawn, Chicago
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Top-rated apartment rentals in Woodlawn, 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 Woodlawn, Chicago apartment rentals
Weekly apartment rentals
Apartment in Uptown
4.96 out of 5 average rating, 265 reviewsCozy loft in Chicago's Uptown
Oct 16 – 23
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
4.94 out of 5 average rating, 191 reviewsSpacious, light-drenched studio-private entrance!
Jul 13 – 20
Apartment in Chicago
4.84 out of 5 average rating, 130 reviewsPerfect Private Getaway in Perfect Pilsen
Oct 5 – 12
Apartment in Avondale
4.97 out of 5 average rating, 117 reviewsDesigner Avondale Attic
Jul 11 – 18
Apartment in Chicago
4.91 out of 5 average rating, 110 reviewsNEW Modern 2BRD apartment| 5min to McCormick Place
Dec 30 – Jan 6
Apartment in Chicago
4.89 out of 5 average rating, 370 reviewsGreat Location Studio in the Gold Coast!!
Jan 22 – 29
Apartment in Chicago
4.81 out of 5 average rating, 143 reviewsThe Posh Apt. Mins to Downtown & Hyde Park
Jul 17 – 24
Private apartment rentals
Apartment in Chicago
4.96 out of 5 average rating, 237 reviewsRoscoe Village One Bed Lux Apartment Near Wrigley
Nov 3 – 10
Apartment in Blue Island
4.93 out of 5 average rating, 264 reviewsCharming Unique 2 Bdrm Apartment in Victorian Home
Oct 26 – Nov 2
Apartment in West Town
4.89 out of 5 average rating, 473 reviewsiKlektik House Chicago / Robin
Dec 10 – 17
Apartment in Chicago
4.97 out of 5 average rating, 251 reviewsSpacious 1BR apartment in a central location
Sep 23 – 30
Apartment in Oak Lawn
4.95 out of 5 average rating, 123 reviewsCharming One Bedroom Apartment
Jul 11 – 18
Apartment in Chicago
4.96 out of 5 average rating, 322 reviewsBright family-friendly Lincoln Square 2-bed 1-bath
Dec 10 – 17
Apartment in Woodlawn
5.0 out of 5 average rating, 6 reviewsRenovated Retreat near U of Chicago
Sep 9 – 16
Apartment in Hyde Park
5.0 out of 5 average rating, 3 reviewsModern 1BR Chicago Hideaway
May 1 – 8
Apartment rentals with a hot tub
Apartment in Chicago
4.86 out of 5 average rating, 155 reviewsStunning Panoramic Chicago Views & Free Parking
Nov 2 – 9
Apartment in West Town
4.88 out of 5 average rating, 393 reviewsCheckerboard Studio with Private Outdoor Hot Tub and Yard
Oct 9 – 16
Apartment in Berwyn
4.91 out of 5 average rating, 202 reviews“Dream slice of urban homesteading.”
Feb 10 – 17
Apartment in Chicago
4.87 out of 5 average rating, 106 reviewsCloud9 |XL Penthouse+Movie Theater+Gym |The Harper
May 15 – 22
Apartment in Logan Square
4.93 out of 5 average rating, 28 reviewsLuxe Suite + Spa House Retreat! Pets Welcome
Mar 10 – 17
Apartment in West Rogers Park
5.0 out of 5 average rating, 16 reviewsSpacious Beautiful Condo
Oct 14 – 21
Apartment in Streeterville
5.0 out of 5 average rating, 9 reviewsLake, City, & River View Condo
May 6 – 13
Apartment in The Loop
4.79 out of 5 average rating, 24 reviewsThe Professional's Playground
Jan 2 – 9
Quick stats about apartment rentals in Woodlawn, Chicago
Total rentals
100 properties
Wifi availability
100 properties include access to wifi
Rentals with dedicated workspaces
70 properties have a dedicated workspace
Pet-friendly rentals
20 properties allow pets
Family-friendly rentals
50 properties are a good fit for families
Total number of reviews
2.3K reviews
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