
Vacation rentals with outdoor seating in South Side
Find and book unique accommodations with outdoor seating on Airbnb
Top-rated accommodations with outdoor seating in South Side
Guests agree: these accommodations with outdoor seating 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 outdoor seating rentals
House rentals with outdoor seating

Chicago Home (1st floor) by Midway near Downtown

The Architectural Haven

3BD Home Mins from Airport | Free Wi-Fi + Parking

Experience Chicago from Our 3-Story Retreat

Animal House near Sox stadium

Get Cozy at a Powder-Blue Residence in the Heart of Pilsen

Boho Chic Coach House 30Min to downtown W/ Parking

Gorgeous 2Bedroom House…
Apartment rentals with outdoor seating

Beautiful European Apartment

Sunny 1 bedroom apartment 1 block from restaurants

*A Happy (City) Glamping- walk to train FREE park

Designer Avondale Attic

Breathtaking & Chic Oasis Loc in Desirable Old Twn

COZY 2Bdr Apt near MDW, Dwtn, United Ctr, Sox, Hwy

2 bedroom apartment near train line and bus lines!

Private apartment with retro vibe
Condo rentals with outdoor seating

"Bliss of Evanston" 180°view, 2BDR +2Bath Urbanlux

NEW luxury Old Town 1-Bedroom condo

Logan Square Beauty with 2 Bedrooms W/parking

Downtown Chicago - Spa Bath, Patio, 3 blocks to L

Spacious 4 Bedroom Condo

Wicker Park/Bucktown condo with large balcony

Updated Designer Duplex In Fulton Market W/parking

Spacious Evanston Unit - Walk to Northwestern U
Destinations to explore
- Downtown Chicago Vacation rentals
- Milwaukee Vacation rentals
- Lake Geneva Vacation rentals
- West Side Vacation rentals
- North Side Vacation rentals
- South Bend Vacation rentals
- South Haven Vacation rentals
- Saugatuck Vacation rentals
- Lake Michigan Beach Vacation rentals
- Evanston Vacation rentals
- New Buffalo Vacation rentals
- Chicago Vacation rentals
- Rentals with a patio South Side
- Rentals with an EV charger South Side
- Condo rentals South Side
- Family-friendly rentals South Side
- Rentals with a firepit South Side
- Townhouse rentals South Side
- Apartment rentals South Side
- Bed and breakfasts South Side
- Rentals with a washer and dryer South Side
- Pet-friendly rentals South Side
- Rentals with a fireplace South Side
- Rentals with lake access South Side
- House rentals South Side
- Rentals with beach access South Side
- Waterfront rentals South Side
- Rentals with a hot tub South Side
- Fitness-friendly rentals South Side
- Rentals with pools South Side
- Rentals with breakfast South Side
- Smoking-friendly rentals South Side
- Kid-friendly rentals South Side
- Private suite rentals South Side
- Rentals with outdoor seating Chicago
- Rentals with outdoor seating Cook County
- Rentals with outdoor seating Illinois
- Rentals with outdoor seating United States
- Cabins United States
- Treehouses United States
- Tiny Houses United States
- Beach Houses United States
- Lakehouses United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Millennium Park
- Wrigley Field
- United Center
- Navy Pier
- Six Flags Great America
- Oak Street Beach
- Shedd Aquarium
- Humboldt Park
- Frank Lloyd Wright Home and Studio
- Guaranteed Rate Field
- 875 North Michigan Avenue
- Lincoln Park
- The Field Museum
- Washington Park Zoo
- Brookfield Zoo
- Museum of Science and Industry
- Illinois Beach State Park
- Garfield Park Conservatory
- Wicker Park
- Lincoln Park Zoo
- Willis Tower
- Raging Waves Waterpark
- The 606
- Chicago Cultural Center