
Townhome vacation rentals in South Side
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Top-rated townhouse rentals in South Side
Guests agree: these townhouse rentals are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for South Side townhouse rentals
Family-friendly townhouse rentals

Beautiful Spacious RiverWest Townhome 4-Bed/4-Bath

The Nancy’s gorgeous , Spacious Urban Getaway

Downtown Elegance ✨ Private Yard Parking

Private Bedroom w/ bath in Chicago Downtown/Loop

Insta Worthy Prime Spot *Patio *Parking *Fireplace

Cozy basement with private Bathroom

Spacious garden level suite

Entire House/United Center /Garage-Walk to Train
Townhouse rentals with a washer and dryer

Chicago West Town Row House

Modern Downtown Home with 5 Baths & Private Garage

★Chicago's hidden gem-private patio, free parking★

Historic Alta Vista Terrace District

Stylish Chicago Duplex Close to Parks & Dtwn

Pulaski Mahal - 3Bed/2.5 Bath w/huge Game Room

B 10minDowntown WasherDryer Townhome SmartTV

Ultra Modern Wicker Park Pad w/ HUGE Outdoor Space
Townhouse rentals with a patio

A Pleasant Stay in Oak Park

Cozy & Bright Townhome near O’hare -Self Check In-

3-Story,Free Parking,No Pet Fee,Private Patio,W/D

Northside Famlynest Lincoln Sq 4BR/1.5BA/2P

Chinatown 3 bedroom with Parking - near McCormick

Old Town/Lincoln Park Luxury Home Garage & Rooftop

Vital Urban: Spa Inspired Retreat

𓃥Wicker Cozy Corner w/Parking on site
Destinations to explore
- Downtown Chicago Vacation rentals
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- Condo rentals South Side
- Bed and breakfasts South Side
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- House rentals South Side
- Rentals with a washer and dryer South Side
- Waterfront rentals South Side
- Private suite rentals South Side
- Pet-friendly rentals South Side
- Family-friendly rentals South Side
- Rentals with beach access South Side
- Smoking-friendly rentals South Side
- Rentals with a fire pit South Side
- Rentals with outdoor seating South Side
- Rentals with breakfast South Side
- Rentals with pools South Side
- Apartment rentals South Side
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- Rentals with a patio South Side
- Kid-friendly rentals South Side
- Rentals with a fireplace South Side
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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