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Vacation rentals in South Side

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in South Side

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

Private room in Chicago
Comfy Bedroom unit 2 | room # 1 – 25min Downtown
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.
$50 per night
Apartment in Chicago
Classic HP 1BR with Fast Transit to UChicago
Hyde Park is home to the University of Chicago, the kind of place where they discover the universe is expanding. Expand your own cultural universe when you stay in this eclectic neighborhood, home to Frank Lloyd Wright’s Robie House, theaters, parks, and plenty of culinary destinations both seasoned (get it?) and new. Your suite includes one bedroom, a full kitchen, washer/dryer, and expansive entertainment options - and several convenient transit options to UChicago campus.
$146 per night
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!
$102 per night

Other great vacation rentals in South Side

Private room in Chicago
Charming Room in Chicago
$52 per night
Private room in Chicago
Private Unit001, McCormick,Chinatown,SOX,GrantPark
$98 per night
Private room in Chicago
Hidden Gem With Convenient Access to Downtown
$37 per night
Private room in Chicago
Perfect Oasis 4mins walk to University & hospital
$48 per night

Other types of stays on Airbnb

  1. Airbnb
  2. United States
  3. Illinois
  4. Cook County
  5. Chicago
  6. South Side