
Vacation rentals in Old Town
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Top-rated vacation rentals in Old Town
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Vacation rentals for every style
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Popular amenities for Old Town, Chicago vacation rentals
Private Old Town, Chicago vacation rentals

Modern 3BR with Private Rooftop & Free Parking

Flat in Lincoln Park 2-Flat Central to Everything

Archways at the Lincoln Park Zoo 2bed/2ba

Chic retreat near the best of Lakeview & Wrigley

Cool Quiet Coach House, Private Access + Patio

East Lakeview Designer Condo with 2 Bd, 2 Bath

5-Star Gold Coast Experience in a Luxe 2BR Retreat

The Belden Belle: The Luxurious Chicago Townhouse
Old Town, Chicago apartment rentals

Bucktown Brick Cottage Apartment

Unwind in Style Steps from the Magnificent Mile

The Noble Farmhouse, w/ Garden in West Town

Lincoln Park Charm + On site Parking Included!

Peaceful River West, free parking

Colorful Bucktown Garden Apartment

Great Location Studio III

Kasa | Views from your Private Balcony | Chicago
Private Old Town, Chicago apartments

*Brand New* Lincoln Park Remarkable

Penthouse Near Wrigley Field

Chic 2BR| 1 FREE Parking& Laundry| Self Checkin

Large condo w/ amazing roof deck

Coach House in Historic Old Town Chicago

The Picasso: #1 Chicago Location

Belmont Pleasures - hot tub / arcade gaming room

Newly Renovated, Spacious 2BR in Andersonville
Quick stats about vacation rentals in Old Town
Total rentals
70 properties
Nightly prices starting at
€ 60 before taxes and fees
Total number of reviews
6.7K reviews
Family-friendly rentals
50 properties are a good fit for families
Pet-friendly rentals
30 properties allow pets
Rentals with dedicated workspaces
40 properties have a dedicated workspace
Destinations to explore
- Lincoln Park
- Wrigley Field
- Millennium Park
- United Center
- Navy Pier
- Six Flags Great America
- Shedd Aquarium
- 875 North Michigan Avenue
- Humboldt Park
- Guaranteed Rate Field
- Frank Lloyd Wright Home and Studio
- Oak Street Beach
- The Field Museum
- Wicker Park
- Garfield Park Conservatory
- Lincoln Park Zoo
- Brookfield Zoo
- Museum of Science and Industry
- Illinois Beach State Park
- Washington Park Zoo
- Willis Tower
- The Beverly Country Club
- Raging Waves Waterpark
- The 606