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Vacation rentals in South Side

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Top-rated vacation rentals in South Side

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

SUPERHOST
  1. Private room
  2. Chicago
BRONZEVILLE OASIS I - Mins to UChicago & The Loop

Perfect oasis for STUDENTS, PROFESSIONALS and VACATIONERS. 5-7 Mins to UofC & IIT. 15 minutes to downtown Chicago & main attractions on Lakeshore Drive such as, McCormick Place & Soldier Field. This will be your home away from home.

$44 per night
  1. Private room
  2. Chicago
Room B5

The room is private. But the apartment including bathroom is shared. Two rooms per unit. A maximum of four people will stay at the apartment. Two per room max. However, only two guests stay at each apartment 98% of the time. Everything is brand new and it’s cleaned constantly. Our house rules include that guests maintain the premises clean and noise level low after 10pm so everybody can have a pleasant stay. For your comfort we offer complementary use of hair drier, iron, ironing board, basic cooking and eating utensils, Netflix, books to read on premises. Etc. Feel free to use all the apartment and building common areas. A garage parking spot could be rented to longer stay guests upon request and depending availability at the moment.

$24 per night
SUPERHOST
  1. Entire rental unit
  2. Chicago
Bridgeport LR Renovated Loft Studio MONTHLY

Please make sure to review "Getting Around" details within the "Neighborhood" section. Nearest building intersection is 32nd Pl. & Carpenter St. to map transit options Newly remodeled loft-style apartment with modern finishes, smart tech & security, in a hip, central neighborhood minutes from downtown Chicago and part of all that trendy Bridgeport has to offer Managed by a seasoned team specializing in monthly furnished rentals Per the City of Chicago ordinances, 31 night minimum on all stays

$40 per night

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Stay near South Side's top sights

Photo of Museum of Science and Industry, Chicago
Museum of Science and Industry, Chicago184 locals recommend
Photo of Frederick C. Robie House
Frederick C. Robie House32 locals recommend
Photo of McCormick Place
McCormick Place61 locals recommend
Photo of University of Chicago: Hyde Park
University of Chicago: Hyde Park5 locals recommend
Photo of South Shore Cultural Center
South Shore Cultural Center9 locals recommend
Photo of McCormick Place
McCormick Place61 locals recommend

Other great vacation rentals in South Side

  1. Private room
  2. Chicago
Room B7
$23 per night
  1. Private room
  2. Chicago
Luxury BR w/private bath 4mins to Univ & Hospital
$50 per night
SUPERHOST
  1. Entire guesthouse
  2. Chicago
Private Studio in Bridgeport, Chicago
$75 per night
SUPERHOST
  1. Private room
  2. Chicago
Downtown Chicago 8 minutes away SELF CHECK IN
$44 per night
SUPERHOST
  1. Private room
  2. Chicago
Comfy Bedroom unit 2 | room # 1 – 25min Downtown
$49 per night
SUPERHOST
  1. Entire rental unit
  2. Chicago
Bridgeport 2R Renovated 2bed/1bath Apt. MONTHLY
$40 per night
  1. Private room
  2. Chicago
Room T6
$35 per night
  1. Private room
  2. Chicago
Full bed w/Netflix near , UofChicago, and train
$42 per night
SUPERHOST
  1. Private room
  2. Chicago
BRONZEVILLE OASIS II- Mins to UChicago & The Loop
$48 per night
  1. Private room
  2. Chicago
Homey, Energy Efficient 3 & Separate Laundry Room.
$37 per night
  1. Private room
  2. Chicago
Room B6
$24 per night
SUPERHOST
  1. Entire guest suite
  2. Chicago
Bridgeport LF Renovated Loft Studio MONTHLY
$40 per night
  1. Airbnb
  2. United States
  3. Illinois
  4. Cook County
  5. Chicago
  6. South Side