
Private suite holiday rentals in South Side
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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

New Bright & Airy Entire Unit in Logan

Cozy Logan Square 2 Bedroom Guest Space

2 Bedroom Apartment by O'Hare/CTA/I90 Free Parking

Tropical Bungalow Getaway in Quiet Neighborhood

Contemporary, private suite w fireplace

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

Wrigleyville/Boystown/Entire Private Floor!

The Deer Suite
Self-Contained Unit with a patio

Oak Lawn remote workers retreat

Comfy suite w/ steam shower near McCormick Place

The Hidden Beach House

Skylit Penthouse | Luxe Rain Shower, Church View

Logan Square’s Garden apt style rental

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

ENC-Chi Arts Stu Near United Ctr & 12 mins to Loop

Cozy Albany Park Garden Unit
Private suite rentals with a washing machine and dryer

Casita Plzeň Guest Suite

Travelers Retreat in Old Town Chicago

Peaceful Portage Park Apartment

A guest suite centrally located, but so quiet

Stylish Studio in Historic Logan Square

Gorgeous Studio 15 Minutes From Ohare!

Lincoln Square In-laws Suite: Private Entrance
Wicker Park Historical District Guest Suite
Destinations to explore
- Chicago Holiday rentals
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- Rentals with a washing machine and dryer South Side
- Rentals with lake access South Side
- Bed and breakfasts South Side
- Rentals with outdoor seating South Side
- Family-friendly rentals South Side
- House rentals South Side
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- Apartment rentals South Side
- Smoking-friendly rentals South Side
- Rentals with a hot tub South Side
- Condo rentals South Side
- Rentals with a fire pit South Side
- Pet-friendly rentals South Side
- Waterfront rentals South Side
- Townhouse rentals South Side
- Rentals with an EV charger South Side
- Rentals with breakfast South Side
- Rentals with a patio South Side
- Rentals with a fireplace South Side
- Rentals with beach access South Side
- Rentals with pools South Side
- Private suite rentals Chicago
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- Private suite rentals United States
- Lincoln Park
- Wrigley Field
- Millennium Park
- United Center
- Navy Pier
- Six Flags Great America
- Shedd Aquarium
- 875 North Michigan Avenue
- Humboldt Park
- Guaranteed Rate Field
- Frank Lloyd Wright Home and Studio
- Oak Street Beach
- The Field Museum
- Wicker Park
- Garfield Park Conservatory
- Lincoln Park Zoo
- Brookfield Zoo
- Museum of Science and Industry
- Illinois Beach State Park
- Washington Park Zoo
- Willis Tower
- The Beverly Country Club
- Raging Waves Waterpark
- The 606