Apartment vacation rentals in Old Town, Chicago
Find and book unique apartments on Airbnb
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 Chicago
4.9 out of 5 average rating, 258 reviewsBright & Lofty Bucktown 1br
Dec 9 – 16
Apartment in Wicker Park
4.97 out of 5 average rating, 237 reviewsStylish First Flr. Studio. Best Location Division+Hermitage.
Feb 23 – Mar 2
Apartment in Logan Square
4.93 out of 5 average rating, 208 reviewsCozy Private Coach House
Sep 2 – 9
Apartment in Uptown
4.96 out of 5 average rating, 267 reviewsCozy loft in Chicago's Uptown
Oct 18 – 25
Apartment in Wrigleyville
4.93 out of 5 average rating, 187 reviewsTaj Ma-small at Wrigley
Feb 24 – Mar 3
Apartment in Logan Square
4.97 out of 5 average rating, 91 reviewsLogan Square 2nd Floor Chicago Victorian
Nov 20 – 27
Apartment in Avondale
4.97 out of 5 average rating, 119 reviewsDesigner Avondale Attic
Jul 8 – 15
Apartment in West Town
4.89 out of 5 average rating, 473 reviewsiKlektik House Chicago / Robin
Dec 2 – 9
Private apartment rentals
Apartment in Lincoln Park
4.99 out of 5 average rating, 158 reviewsSettle Inn Lincoln Park
Aug 5 – 12
Apartment in Little Italy
4.98 out of 5 average rating, 199 reviewsSpacious 2BR on Quiet St - Free Park/Late Checkout
Jan 9 – 16
Apartment in Lincoln Square
4.93 out of 5 average rating, 112 reviewsBright family-friendly Lincoln Square 2-bed 1-bath
Nov 20 – 27
Apartment in Logan Square
4.96 out of 5 average rating, 376 reviewsKing Bed, Huge Spa Shower, Dining Destination
Jan 5 – 12
Apartment in Wicker Park
4.77 out of 5 average rating, 84 reviewsPrivate Studio Apt in the Heart of Wicker Park!
Dec 17 – 24
Apartment in Wicker Park
4.96 out of 5 average rating, 95 reviewsNewly remodeled 1BR! Only 5 MIN walk to BLUE LINE!
Oct 28 – Nov 4
Apartment in Logan Square
4.91 out of 5 average rating, 373 reviewsThe Grotto of Logan Square
Sep 21 – 26
Apartment in Wicker Park
4.84 out of 5 average rating, 480 reviewsRelaxed Bucktown/Wicker Park 1B Apt
Oct 17 – 24
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
Apr 20 – 27
Apartment in Magnificent Mile
4.87 out of 5 average rating, 75 reviews4Br Gold Coast Duplex w Jacuzzi in the Bedroom!
Mar 19 – 26
Apartment in West Loop
5.0 out of 5 average rating, 10 reviewsSkyline Oasis: City & Lake Views
Jul 15 – 22
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 West Town
4.88 out of 5 average rating, 42 reviewsCloud 9 | Presidential Penthouse Suite | The Iris
Nov 12 – 19
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
€ 65 before taxes and fees
Destinations to explore
- Apartment rentals United States
- Serviced apartment rentals United States
- Apartment rentals Chicago
- Apartment rentals Chicago
- Apartment rentals Downtown Chicago
- Apartment rentals Milwaukee
- Apartment rentals Illinois
- Rentals with a fireplace Old Town
- Monthly Rentals Old Town
- Pet-friendly rentals Old Town
- Rentals with a patio Old Town
- Family-friendly rentals Old Town
- Rentals with a washer and dryer Old Town
- Rentals with outdoor seating Old Town
- Apartment rentals Cook County
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom