
Private suite holiday rentals in South Side
Find and book unique Self-Contained Units on Airbnb
Top-rated Self-Contained Units in South Side
Guests agree: These Self-Contained Units 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 South Side Self-Contained Units
Family-friendly private suite rentals

2 King Beds /Easy Downtown / Free Str Parking-Read

A guest suite centrally located, but so quiet

Tropical Bungalow Getaway in Quiet Neighborhood

Private suite in Lincoln Square

Cozy Home Living, Dogs, Kids, Free Parking, 420 OK

Cozy, Quiet, Garden Getaway!

Wrigleyville/Boystown/Entire Private Floor!

Secret Garden @ The Noble Farmhouse | Wicker Park
Self-Contained Unit with a patio

Comfy suite w/ steam shower near McCormick Place

Comfortable and Cozy Suite in Quiet Neighborhood

The Hidden Beach House

Urban Penthouse- Lux Rain Shower, Church View

Logan Square’s Garden apt style rental

Logan Square Chicago 2BR cottage, close to it all!

2BR Logan Sq Mini-Resort stay + Pet friendly

The Windy City Mint
Private suite rentals with a washing machine and dryer

New Bright & Airy Entire Unit in Logan

Travelers Retreat in Old Town Chicago

Peaceful Portage Park Apartment

Private Suite w/ offstreet pkg, at Logan Sq Blu Ln

Contemporary, private suite w fireplace

Spacious Garden Unit • Private Entry + Parking

Adorable studio style unit - Self check in ⚡️

Gorgeous Studio 15 Minutes From Ohare!
Destinations to explore
- Downtown Chicago Holiday rentals
- Milwaukee Holiday rentals
- Lake Geneva Holiday rentals
- West Side Holiday rentals
- North Side Holiday rentals
- South Bend Holiday rentals
- South Haven Holiday rentals
- Saugatuck Holiday rentals
- Lake Michigan Beach Holiday rentals
- Evanston Holiday rentals
- New Buffalo Holiday rentals
- Chicago Holiday rentals
- Smoking-friendly rentals South Side
- Bed and breakfasts South Side
- Rentals with breakfast South Side
- Condo rentals South Side
- Rentals with outdoor seating South Side
- Rentals with a fire pit South Side
- Rentals with a hot tub South Side
- House rentals South Side
- Rentals with a patio South Side
- Apartment rentals South Side
- Waterfront rentals South Side
- Rentals with beach access South Side
- Pet-friendly rentals South Side
- Townhouse rentals South Side
- Rentals with lake access South Side
- Rentals with a fireplace South Side
- Rentals with a washing machine and dryer South Side
- Family-friendly rentals South Side
- Fitness-friendly rentals South Side
- Kid-friendly rentals South Side
- Rentals with pools South Side
- Rentals with an EV charger South Side
- Private suite rentals Chicago
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- Dog-Friendly Cottages United Kingdom
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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