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Holiday rentals in South Side

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Top-rated holiday rentals in South Side

Guests agree: these stays are highly rated for location, cleanliness, and more.

Private room in Chicago
Living in a dream (unit 2 room #5)
A place you can come to and make memories. Hop on the CTA for a quick ride downtown, 20 minutes, to enjoy shopping and family friendly activities. You can also stay in to relax and enjoy coffee, tea, or hot chocolate at the self serve coffee bar. For a little more in house excitement, hang out in the photo / game room and have fun playing 2,000+ arcade games. You can also enjoy the Smart Tv to binge-watch all your favorite shows on Netflix. The perfect Airbnb for your next Chicago getaway.
₹2,255 per night
SUPERHOST
Guest house in Chicago
Private Studio in Bridgeport, Chicago
A bright studio guesthouse, perfect for business travelers, a couple’s getaway, personal retreat, or a solo adventurer. Has a kitchen sink, cabinet space for your non-perishable items, a microwave, mini-fridge, and Keurig. We provide plates, flatware, mugs, and glasses. The studio offers the privacy of your own bathroom and shower facilities. You'll rest well in a full-size Murphy bed, with sufficient storage for all your travel items. A couch is available for a third guest if needed.
₹4,489 per night
SUPERHOST
Private room in Chicago
Sophisticated King Bedroom
Steps from the UChicago and the UChicago Hospital with easy access to downtown. Private bathroom and plenty of space. It is perfect for a weekend away, a visit to the University of Chicago, or a rotation at the hospital. I live in the condo part-time with my dogs and would be delighted to have you stay. Your visit directly supports my rescue dogs' needs and is much appreciated! Early check-ins and late check-outs are okay!
₹4,966 per night
SUPERHOST

Holiday rentals for every style

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Stay near South Side's top sights

Photo of Museum of Science and Industry
Museum of Science and Industry483 locals recommend
Photo of South Shore Cultural Center
South Shore Cultural Center37 locals recommend
Photo of Ping Tom Memorial Park
Ping Tom Memorial Park39 locals recommend
Photo of University of Chicago
University of Chicago19 locals recommend
Photo of Burnham Park
Burnham Park7 locals recommend
Photo of Frederick C. Robie House
Frederick C. Robie House66 locals recommend

Other great holiday rentals in South Side

Private room in Chicago
City View near Downtown Chicago Sox & Chinatown
₹2,524 per night
Home in Chicago
Exclusive and Spacious Pilsen Guest House
₹2,214 per night
SUPERHOST
Private room in Chicago
Luxury Stay near Downtown Chicago New Queen Bed
₹3,082 per night
Rental unit in Chicago
!3R Location! 2bed/2bath StepstoSouthLoop +Laundry
₹6,839 per night
SUPERHOST
Rental unit in Chicago
Deluxe Modern 2BR Apt 4min walk to UofC & Hospital
₹7,246 per night
Rental unit in Chicago
Bridgeport_cp 1F Open Live/Work Apt + Free Laundry
₹5,780 per night
SUPERHOST
Rental unit in Chicago
Pilsen 3R 1bed/1bath + Free Laundry +GreatLocation
₹3,489 per night
SUPERHOST
Private room in Chicago
Luxury BR w/private bath 4mins to Univ & Hospital
₹4,071 per night
Private room in Chicago
A comfortable retreat in a vintage city cottage
₹1,872 per night
SUPERHOST
Rental unit in Chicago
Bridgeport_cp 3R 2bed/1bath + Free Laundry
₹6,187 per night
SUPERHOST
Loft in Chicago
Grand Studio in the Heart of Lakeview!
₹4,176 per night
SUPERHOST
Rental unit in Chicago
!1F Location! 2bed/1bath StepstoSouthLoop +Laundry
₹5,536 per night
SUPERHOST
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