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 Lincoln Park
4.87 out of 5 average rating, 193 reviewsNew! Beautiful 2BR Apartment in Old Town
Oct 25 – Nov 1
Apartment in Lincoln Park
4.86 out of 5 average rating, 188 reviewsPerfect Lincoln Park Retreat - Walk to Depaul!
Jan 21 – 28
Apartment in Chicago
4.9 out of 5 average rating, 258 reviewsBright & Lofty Bucktown 1br
Dec 9 – 16
Apartment in Wrigleyville
4.93 out of 5 average rating, 187 reviewsTaj Ma-small at Wrigley
Feb 24 – Mar 3
Apartment in Logan Square
4.93 out of 5 average rating, 208 reviewsCozy Private Coach House
Sep 2 – 9
Apartment in Avondale
4.95 out of 5 average rating, 43 reviewsDesigner Avondale Attic
Jul 8 – 15
Apartment in Uptown
4.96 out of 5 average rating, 267 reviewsCozy loft in Chicago's Uptown
Oct 18 – 25
Apartment in Lincoln Park
4.89 out of 5 average rating, 145 reviewsChicago Lincoln Park North Pond 2 Bedroom Pied-à-Terre
Nov 17 – 24
Private apartment rentals
Apartment in Wicker Park
4.96 out of 5 average rating, 96 reviewsNewly remodeled 1BR! Only 5 MIN walk to BLUE LINE!
Oct 28 – Nov 4
Apartment in Lake View
4.86 out of 5 average rating, 202 reviewsPrivate Queen Bedroom and En Suite Bath
Jul 19 – 26
Apartment in West Town
4.92 out of 5 average rating, 327 reviewsBright, Modern Apartment in a Vintage Greystone
Apr 14 – 21
Apartment in West Town
4.89 out of 5 average rating, 473 reviewsiKlektik House Chicago / Robin
Dec 2 – 9
Apartment in Lincoln Square
4.96 out of 5 average rating, 323 reviewsBright family-friendly Lincoln Square 2-bed 1-bath
Nov 20 – 27
Apartment in West Town
4.98 out of 5 average rating, 221 reviewsUkrainian Village Garden Retreat
Dec 17 – 24
Apartment in Wicker Park
4.78 out of 5 average rating, 219 reviewsPrivate Studio Apt in the Heart of Wicker Park!
Dec 20 – 27
Apartment in Lake View
4.88 out of 5 average rating, 190 reviewsComfort zone
Oct 18 – 25
Apartment rentals with a hot tub
Apartment in West Town
4.88 out of 5 average rating, 394 reviewsCheckerboard Studio with Private Outdoor Hot Tub and Yard
Sep 4 – 11
Apartment in Berwyn
4.91 out of 5 average rating, 204 reviews“Dream slice of urban homesteading.”
Sep 30 – Oct 7
Apartment in Logan Square
4.91 out of 5 average rating, 32 reviewsLuxe Suite + Spa House Retreat! Pets Welcome
Jan 26 – Feb 2
Apartment in Magnificent Mile
4.87 out of 5 average rating, 75 reviews4Br Gold Coast Duplex w Jacuzzi in the Bedroom!
Apr 23 – 30
Apartment in West Loop
5.0 out of 5 average rating, 10 reviewsSkyline Oasis: City & Lake Views
Jun 27 – Jul 4
Apartment in West Rogers Park
4.86 out of 5 average rating, 21 reviewsSpacious Beautiful Condo
Oct 14 – 21
Apartment in The Loop
5.0 out of 5 average rating, 7 reviewsThe Downtown Oasis (2BD / 2BA)
Nov 17 – 24
Apartment in Belmont Cragin
5.0 out of 5 average rating, 27 reviewsBelmont Pleasures - hot tub / arcade gaming room
Mar 22 – 29
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
G$14,605 GYD before taxes and fees
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