
Apartment holiday rentals in Old Town, Chicago
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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

Old Town Two Floor Duplex Condo

Lincoln park getaway, Outdoor patio! Summer Fun!

Coach House in Historic Old Town Chicago

The Picasso: #1 Chicago Location

Comfortable & Modern Studio in City Center 1 Bath

The Heart of Bucktown

River North | Private Balcony With In&Out Parking

Charming Old Town Getaway Near Chicago Attractions
Private apartment rentals

Pristine Gold Coast 3BD|2BA | Free Parking| Beach.

Cozy Lincoln Park Retreat | Walk to Dining & Parks

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

Parking! Charming Lincoln Park Flat! 3 Comfy Beds!

Large condo w/ amazing roof deck

Luxury Lincoln Park Retreat 2BR 2LR Dublex

Humboldt Park Loft

Heart of Lincoln park
Apartment rentals with a hot tub

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

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

Checkerboard Studio, Private Outdoor Hot Tub, Yard
Quick stats about flat rentals in Old Town, Chicago
Total rentals
30 properties
Nightly prices starting at
$90 SGD before taxes and fees
Total number of reviews
3.6K 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
- Navy Pier
- United Center
- 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
- Museum of Science and Industry
- Garfield Park Conservatory
- Willis Tower
- Lincoln Park Zoo
- Illinois Beach State Park
- Brookfield Zoo
- Wicker Park
- Washington Park Zoo
- Raging Waves Waterpark
- The 606
- The Beverly Country Club