
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

Flat in Lincoln Park 2-Flat Central to Everything

Modern Apt with style & comfort in Pilsen Chicago

Cool Quiet Coach House, Private Access + Patio

Lincoln Paradise– Steps to Park & Zoo!

East Lakeview Designer Condo with 2 Bd, 2 Bath

Luxury SOHO Styled Two-Level Townhouse | Old Town

Wrigleyville Southport Studio

Modern Luxury In Old Town - Sleeps 4
Old Town, Chicago apartment rentals

Modern 3BR with Private Rooftop & Free Parking

Perfect Lincoln Park Retreat - Walk to Depaul!

Bucktown Brick Cottage Apartment

Spacious & private! Free parking! Great location!

*BRAND NEW* Lincoln Park GEM

Logan Square Studio

Unwind in Style Steps from the Magnificent Mile

The Noble Farmhouse, w/ Garden in West Town
Private Old Town, Chicago apartments

iKlektik House Chicago/Robin

Spacious Studio w/Balcony in Bucktown/Wicker Park

Stylish 2BR stunner w/ unbeatable location

CUTE, PRIVATE & QUITE STUDIO 1BD/1BA Wicker Park!!

Newly-renovated historic home in Logan Square

The Grotto of Logan Square

Cityscape - Heart of Lincoln Park/DePaul

Ukrainian Village Garden Retreat
Quick stats about vacation rentals in Old Town
Total rentals
70 properties
Nightly prices starting at
G$14,648 GYD 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
- Millennium Park
- Wrigley Field
- United Center
- Navy Pier
- Six Flags Great America
- Shedd Aquarium
- Humboldt Park
- Guaranteed Rate Field
- 875 North Michigan Avenue
- Frank Lloyd Wright Home and Studio
- Oak Street Beach
- The Field Museum
- Wicker Park
- Lincoln Park Zoo
- Garfield Park Conservatory
- Illinois Beach State Park
- Washington Park Zoo
- Museum of Science and Industry
- Brookfield Zoo
- Willis Tower
- Raging Waves Waterpark
- The Beverly Country Club
- The 606