
Apartment holiday 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.
Holiday 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

Cozy Lincoln Park Retreat | Walk to Dining & Parks

Lincoln park getaway, Outdoor patio! Summer Fun!

Coach House in Historic Old Town Chicago

Chicago Lincoln Park North Pond 1 Bedroom

The Picasso: #1 Chicago Location

Comfortable & Modern Studio in City Center 1 Bath
Explore the City from an Elegant, Urban Retreat

The Noble Farmhouse, w/ Garden in West Town
Private apartment rentals

Brand New 1-BR Apt: Deluxe Comfort w/ Spa Bathroom

River North | Private Deck With In&Out Parking

Old Town Two Floor Duplex Condo

The Bell House: Apartment #1

Large condo w/ amazing roof deck

The Heart of Bucktown

Chicago Luxury Long Term 30+

Luxury Downtown Chicago 2BD-2BA View-Gym-Rooftop
Apartment rentals with a hot tub

Luxe Ranch & Spa, Euro Opulence, a 4-Season Oasis

Spacious Beautiful Condo

Skyline Oasis: City & Lake Views

Luxurious 3BD Penthouse- Private Patio+Gym+Rooftop

Penthouse Near Fulton: Skyline, Spacious

Summer Getaway in Prime Location | Pet Friendly

Belmont Pleasures - hot tub / arcade gaming room

2Bed 2Bath 15min to Wrigley with Parking& Balcony
Quick stats about flat rentals in Old Town, Chicago
Total rentals
20 properties
Nightly prices starting at
£89 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
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- Millennium Park
- Wrigley Field
- United Center
- Navy Pier
- Oak Street Beach
- Six Flags Great America
- Humboldt Park
- Shedd Aquarium
- Guaranteed Rate Field
- 875 North Michigan Avenue
- The Field Museum
- Lincoln Park
- Frank Lloyd Wright Home and Studio
- Brookfield Zoo
- Museum of Science and Industry
- Garfield Park Conservatory
- Washington Park Zoo
- Wicker Park
- Illinois Beach State Park
- Lincoln Park Zoo
- Willis Tower
- Raging Waves Waterpark
- The 606
- The Beverly Country Club