Apartment holiday rentals in Old Town, Chicago
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Top-rated apartment rentals in Old Town, Chicago
Guests agree: these apartments are highly rated for location, cleanliness and more.
Holiday rentals for every style
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Popular amenities for Old Town, Chicago apartment rentals
Weekly apartment rentals
Flat in Wicker Park
4.97 out of 5 average rating, 237 reviewsStylish First Flr. Studio. Best Location Division+Hermitage.
Flat in Lincoln Park
4.8 out of 5 average rating, 123 reviewsThe Biddle House (#2)
Flat in Old Town
4.91 out of 5 average rating, 158 reviewsOLD TOWN TRIUMPHANT 2BD/2BA (+Rooftop&Parking)
Flat in Avondale
4.97 out of 5 average rating, 120 reviewsDesigner Avondale Attic
Flat in Humboldt Park
4.98 out of 5 average rating, 110 reviewsHumboldt Park Loft
Flat in Lincoln Park
4.89 out of 5 average rating, 148 reviewsLincoln Paradise– Steps to Park & Zoo!
Flat in Logan Square
4.96 out of 5 average rating, 380 reviewsKing Bed, Huge Spa Shower, Dining Destination
Flat in Uptown
4.96 out of 5 average rating, 268 reviewsCozy loft in Chicago's Uptown
Private apartment rentals
Flat in Chicago
4.96 out of 5 average rating, 122 reviewsCozy Urban Getaway East Village Apartment
Flat in West Town
4.89 out of 5 average rating, 475 reviewsiKlektik House Chicago / Robin
Flat in Lake View
4.87 out of 5 average rating, 242 reviewsWELCOME TO NANCY'S PAD!
Flat in Lake View
4.93 out of 5 average rating, 171 reviewsCharming Apt. near Wrigley/Cubs, Ravenswood/Uptown
Flat in Wrigleyville
4.8 out of 5 average rating, 387 reviews'Secret Garden' Apartment in Wrigleyville
Flat in Wicker Park
4.96 out of 5 average rating, 250 reviewsNewly remodeled 1BR! Only 5 MIN walk to BLUE LINE!
Flat in East Rogers Park
4.89 out of 5 average rating, 107 reviewsLAKESIDE PIED `A TERRE STEPS TO BEACH
Flat in Wicker Park
4.78 out of 5 average rating, 220 reviewsPrivate Studio Apt in the Heart of Wicker Park!
Apartment rentals with a hot tub
Flat in West Town
4.88 out of 5 average rating, 398 reviewsCheckerboard Studio with Private Outdoor Hot Tub and Yard
Flat in Near South Side
4.87 out of 5 average rating, 160 reviewsSkyline Serenity: Sauna, Hot Tub, Peloton, Views
Flat in Berwyn
4.91 out of 5 average rating, 206 reviews“Dream slice of urban homesteading.”
Flat in West Loop
4.87 out of 5 average rating, 106 reviewsCloud9 |XL Penthouse+Movie Theater+Gym |The Harper
Flat in Logan Square
4.92 out of 5 average rating, 36 reviewsLuxe Suite + Spa House Retreat! Pets Welcome
Flat in Streeterville
5.0 out of 5 average rating, 11 reviewsLake, City, & River View Condo
Flat in West Loop
5.0 out of 5 average rating, 11 reviewsSkyline Oasis: City & Lake Views
Flat in The Loop
4.8 out of 5 average rating, 10 reviewsThe Areal Oasis
Quick stats about flat rentals in Old Town, Chicago
Total rentals
30 properties
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Pet-friendly rentals
10 properties allow pets
Family-friendly rentals
10 properties are a good fit for families
Total number of reviews
3.2K reviews
Nightly prices starting at
€ 65 before taxes and fees
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