Skip to content

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.

Rental unit 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.
$103 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!
$102 per night
SUPERHOST
Private room in Chicago
Fresh and Sunny Bed & Bath by UofC
Our private bed and bath offers high ceilings, a sunny Juliet balcony, comfy Queen bed and fresh, clean finishes, including an airy, open shower. Use us as your base for exploring the city or work as we are steps away from both public trans. and the University of Chicago. It's hard to find a more convenient location in Hyde Park! Welcome!
$82 per night

Other great vacation rentals in South Side

SUPERHOST
Private room in Chicago
Private Unit001, McCormick,Chinatown,SOX,GrantPark
$89 per night
SUPERHOST
Private room in Chicago
Living in a dream (unit 2 room #5)
$46 per night
Private room in Chicago
Hidden Gem With Convenient Access to Downtown
$36 per night
Private room in Chicago
The Hyde Park Haven
$73 per night

Other types of stays on Airbnb

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