Apartment vacation 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.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Old Town, Chicago apartment rentals
Weekly apartment rentals
Apartment in Roscoe Village
4.96 out of 5 average rating, 238 reviewsRoscoe Village One Bed Lux Apartment Near Wrigley
Jan 14 – 21
Apartment in Lincoln Park
4.89 out of 5 average rating, 144 reviewsChicago Lincoln Park North Pond 2 Bedroom Pied-à-Terre
Dec 14 – 21
Apartment in West Town
4.89 out of 5 average rating, 473 reviewsiKlektik House Chicago / Robin
Jan 3 – 10
Apartment in Lincoln Park
4.87 out of 5 average rating, 192 reviewsNew! Beautiful 2BR Apartment in Old Town
Oct 21 – 28
Apartment in Lincoln Square
4.94 out of 5 average rating, 191 reviewsSpacious, light-drenched studio-private entrance!
Jul 22 – 29
Apartment in Wrigleyville
4.8 out of 5 average rating, 385 reviews'Secret Garden' Apartment in Wrigleyville
Sep 10 – 17
Apartment in Logan Square
4.93 out of 5 average rating, 207 reviewsCozy Private Coach House
Oct 1 – 8
Apartment in Logan Square
4.92 out of 5 average rating, 491 reviews2BR Bursting w/ Character in Hip Logan Square!
Apr 6 – 13
Private apartment rentals
Apartment in Lincoln Park
4.99 out of 5 average rating, 158 reviewsSettle Inn Lincoln Park
Oct 4 – 11
Apartment in Avondale
4.97 out of 5 average rating, 117 reviewsDesigner Avondale Attic
Jul 6 – 13
Apartment in Lincoln Park
4.79 out of 5 average rating, 172 reviewsPerfect 1br In Lincoln Park - Steps to Depaul!
Feb 27 – Mar 6
Apartment in Logan Square
4.91 out of 5 average rating, 372 reviewsThe Grotto of Logan Square
Sep 4 – 9
Apartment in Wicker Park
4.78 out of 5 average rating, 217 reviewsPrivate Studio Apt in the Heart of Wicker Park!
Mar 6 – 13
Apartment in Wicker Park
4.96 out of 5 average rating, 247 reviewsNewly remodeled 1BR! Only 5 MIN walk to BLUE LINE!
Sep 3 – 10
Apartment in East Rogers Park
4.89 out of 5 average rating, 105 reviewsLAKESIDE PIED `A TERRE STEPS TO BEACH
Sep 29 – Oct 6
Apartment in Chicago
4.88 out of 5 average rating, 302 reviewsUnwind in the Garden of an elegant, Modern Home
Feb 22 – Mar 1
Apartment rentals with a hot tub
Apartment in West Town
4.88 out of 5 average rating, 393 reviewsCheckerboard Studio with Private Outdoor Hot Tub and Yard
Oct 14 – 21
Apartment in Chicago
4.87 out of 5 average rating, 156 reviewsStunning Panoramic Chicago Views & Free Parking
Nov 1 – 8
Apartment in Berwyn
4.91 out of 5 average rating, 203 reviews“Dream slice of urban homesteading.”
Nov 29 – Dec 6
Apartment in West Loop
4.87 out of 5 average rating, 106 reviewsCloud9 |XL Penthouse+Movie Theater+Gym |The Harper
Feb 18 – 25
Apartment in Streeterville
5.0 out of 5 average rating, 10 reviewsLake, City, & River View Condo
Jul 10 – 17
Apartment in Logan Square
4.9 out of 5 average rating, 30 reviewsLuxe Suite + Spa House Retreat! Pets Welcome
Mar 8 – 15
Apartment in West Loop
5.0 out of 5 average rating, 10 reviewsSkyline Oasis: City & Lake Views
Sep 17 – 24
Apartment in West Rogers Park
4.94 out of 5 average rating, 18 reviewsSpacious Beautiful Condo
Oct 19 – 26
Quick stats about apartment 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
$70 before taxes and fees
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