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 Skokie
4.89 out of 5 average rating, 56 reviewsCharming 2 bed/1 bath apt- walk 2 train/store/rest
Apartment in West Lake View
4.95 out of 5 average rating, 102 reviewsChic retreat near the best of Lakeview & Wrigley
Apartment in Lincoln Square
4.91 out of 5 average rating, 185 reviewsComfortable Vintage North Side Retreat for 8
Apartment in Lincoln Park
4.95 out of 5 average rating, 110 reviewsElegant Depaul Apt on Jonquil Park
Apartment in Irving Park
4.93 out of 5 average rating, 229 reviewsCool and Modern Chicago Apartment near Transit
Apartment in West Town
4.85 out of 5 average rating, 161 reviews*Comfortable & Spacious Home Close to Downtown*
Apartment in Bridgeport
4.93 out of 5 average rating, 107 reviewsCitySlickers Crash Pad /Free Parking /No Clean Fee
Apartment in Lincoln Park
4.73 out of 5 average rating, 204 reviewsRare, Updated 1 BR Condo in Lincoln Park!
Private apartment rentals
Apartment in Oak Park
4.87 out of 5 average rating, 273 reviewsCosmopolitan Nest in Oak Park North Side
Apartment in Near North Side
4.91 out of 5 average rating, 121 reviewsModern 3BR with Private Rooftop & Free Parking
Apartment in East Rogers Park
4.9 out of 5 average rating, 142 reviewsPrivate Garden Apartment GATED FREE Parking
Apartment in Avondale
4.98 out of 5 average rating, 102 reviewsLovely 2bedroom 1bath Apt and outdoor seating.
Apartment in Avondale
4.91 out of 5 average rating, 263 reviewsAvondale Gem: 2BR, Stylish Kitchen, Transit Nearby
Apartment in West Town
4.75 out of 5 average rating, 138 reviewsWicker Park Historic, Art-Filled, Urban Oasis #2
Apartment in Roscoe Village
4.75 out of 5 average rating, 251 reviewsNorth Side Pied-à-terre
Apartment in Roscoe Village
4.77 out of 5 average rating, 267 reviewsClassic 2 Bedroom Roscoe Village Apartment
Apartment rentals with a hot tub
Apartment in Lincoln Park
New place to stayDepaul SelfCheckin WasherDryer 15minstodowntown
Apartment in West Loop
4.82 out of 5 average rating, 72 reviewsQuiet but in the Heart of City walk Everywhere
Apartment in West Rogers Park
4.85 out of 5 average rating, 55 reviewsSpacious Beautiful Condo
Apartment in West Loop
5 out of 5 average rating, 21 reviewsSkyline Oasis: City & Lake Views
Apartment in Chicago
4.85 out of 5 average rating, 53 reviewsHoliday Parties Welcome with 3 nights or more!
Apartment in Belmont Cragin
4.99 out of 5 average rating, 80 reviewsBelmont Pleasures - hot tub / arcade gaming room
Apartment in Streeterville
5 out of 5 average rating, 21 reviewsLake, City, & River View Condo
Apartment in The Loop
4.75 out of 5 average rating, 48 reviewsThe Professional's Playground
Quick stats about apartment rentals in Old Town, Chicago
Total rentals
30 properties
Nightly prices starting at
$144 CAD before taxes and fees
Total number of reviews
3.5K reviews
Family-friendly rentals
10 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Destinations to explore
- Serviced apartment rentals United States
- Apartment rentals United States
- Apartment rentals Chicago
- Apartment rentals Downtown Chicago
- Apartment rentals Milwaukee
- Apartment rentals Illinois
- Serviced apartment rentals Illinois
- House rentals Old Town
- Pet-friendly rentals Old Town
- Rentals with a fireplace Old Town
- Monthly Rentals Old Town
- Rentals with a patio Old Town
- Rentals with outdoor seating Old Town
- Rentals with a washer and dryer Old Town
- Family-friendly rentals 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