
Holiday houses in Old Town
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Top-rated holiday rentals in Old Town
Guests agree: these stays are highly rated for location, cleanliness and more.
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Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Old Town holiday rentals
Other great holiday rentals in Old Town
Top Guest favourite

Home in Old Town Triangle
5 out of 5 average rating, 8 reviewsOld Town Retreat
Superhost

Apartment in Gold Coast
5 out of 5 average rating, 4 reviewsHancock Lookout|Steps to Beach&Transit, CHI Views
Superhost

Apartment in Lincoln Park
4.8 out of 5 average rating, 10 reviewsLarge condo w/ amazing roof deck

Apartment in Lincoln Park
4.84 out of 5 average rating, 102 reviewsSophisticated, 2-BR Condo in Old Town
Top Guest favourite

Apartment in Old Town Triangle
4.97 out of 5 average rating, 30 reviewsThe Picasso: #1 Chicago Location
Guest favourite

Home in Old Town Triangle
4.98 out of 5 average rating, 86 reviewsOpulent 3bdr2bth Old Town Luxury + Parking prmts
Guest favourite

Condo in Near North Side
4.98 out of 5 average rating, 80 reviewsTwo Floor Luxury 3 Bedroom Condo in Old Town
Top Guest favourite

Apartment in Gold Coast
5 out of 5 average rating, 20 reviewsThe Auberge - Luxe Flat Near Lake, Dining, & Shops
Quick stats about holiday rentals in Old Town
Total rentals
70 properties
Nightly prices starting at
$121 NZD 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
- Museum of Science and Industry
- Illinois Beach State Park
- Brookfield Zoo
- Washington Park Zoo
- Willis Tower
- The Beverly Country Club
- Raging Waves Waterpark
- The 606