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
Rental unit in Roscoe Village
4.96 out of 5 average rating, 278 reviewsRoscoe Village One Bed Lux Apartment Near Wrigley
Rental unit in Lake View
4.87 out of 5 average rating, 278 reviewsWELCOME TO NANCY'S PAD!
Rental unit in Wicker Park
4.88 out of 5 average rating, 139 reviewsCharming Two Bedroom in Wicker Park
Rental unit in West Town
4.92 out of 5 average rating, 346 reviewsSpacious & private! Free parking! Great location!
Rental unit in Logan Square
4.87 out of 5 average rating, 300 reviewsLogan Square Video Game Loft
Rental unit in Lake View
4.97 out of 5 average rating, 278 reviewsThe Garden on Wayne
Rental unit in Lake View
4.87 out of 5 average rating, 179 reviewsLovely and Cozy Suite on Southport !
Rental unit in Ukrainian Village
4.98 out of 5 average rating, 256 reviewsUkrainian Village Garden Retreat
Private apartment rentals
Rental unit in Lincoln Square
4.96 out of 5 average rating, 357 reviewsBright family-friendly Lincoln Square 2-bed 1-bath
Rental unit in Logan Square
4.96 out of 5 average rating, 416 reviewsKing Bed, Huge Spa Shower, Dining Destination
Rental unit in West Lake View
4.93 out of 5 average rating, 143 reviewsSun drenched 2 bedroom 1 bath with Kitchen & W/D
Rental unit in Avondale
4.97 out of 5 average rating, 144 reviewsDesigner Avondale Attic
Rental unit in Wicker Park
4.82 out of 5 average rating, 407 reviewsWESTERN AVE ARTISTS LOFTS- Park Free
Rental unit in Little Italy
4.98 out of 5 average rating, 222 reviewsSpacious 2BR on Quiet St - Free Park/Late Checkout
Rental unit in Edgewater
4.93 out of 5 average rating, 413 reviewsRavenswood Guest House Annex
Rental unit in Near North Side
4.94 out of 5 average rating, 143 reviews*Steps to Mag Mile, 2 BD , fast Wi-Fi, W&D
Apartment rentals with a hot tub
Rental unit in Lincoln Park
New place to stayDepaul SelfCheckin WasherDryer 15minsdowntown
Rental unit in West Rogers Park
4.88 out of 5 average rating, 50 reviewsSpacious Beautiful Condo
Rental unit in Chicago
4.85 out of 5 average rating, 53 reviewsPrivate Rooftop Views from Penthouse Suite
Rental unit in West Loop
5 out of 5 average rating, 20 reviewsSkyline Oasis: City & Lake Views
Rental unit in Belmont Cragin
4.99 out of 5 average rating, 74 reviewsBelmont Pleasures - hot tub / arcade gaming room
Rental unit in Streeterville
5 out of 5 average rating, 21 reviewsLake, City, & River View Condo
Rental unit in Roseland
4.94 out of 5 average rating, 49 reviews420 friendly apt with 2 queens,1full roller,1 twin
Rental unit in The Loop
4.75 out of 5 average rating, 44 reviewsThe Professional's Playground
Quick stats about apartment rentals in Old Town, Chicago
Total rentals
30 properties
Nightly prices starting at
G$20,886 GYD 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 Chicago
- Apartment rentals Downtown Chicago
- Apartment rentals Milwaukee
- Apartment rentals Illinois
- Pet-friendly rentals Old Town
- Rentals with a fireplace Old Town
- Rentals with a patio Old Town
- Rentals with a washer and dryer Old Town
- Monthly Rentals Old Town
- Family-friendly rentals 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