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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.

SUPERHOST
  1. Entire guest suite
  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

  1. Private room
  2. Chicago
Room H5

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Stay near South Side's top sights

Photo of Museum of Science and Industry, Chicago
Museum of Science and Industry, Chicago185 locals recommend
Photo of Frederick C. Robie House
Frederick C. Robie House32 locals recommend
Photo of McCormick Place
McCormick Place62 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 Place62 locals recommend

Other great vacation rentals in South Side

SUPERHOST
  1. Private room
  2. Chicago
Cozy Chicago bedroom unit # 2 room # 3
  1. Private room
  2. Chicago
Perfect Oasis 4mins walk to University & hospital
  1. Private room
  2. Chicago
Luxury BR w/private bath 4mins to Univ & Hospital
  1. Private room
  2. Chicago
Room T5
SUPERHOST
  1. Entire guesthouse
  2. Chicago
Private Studio in Bridgeport, Chicago
  1. Private room
  2. Chicago
Room T6
SUPERHOST
  1. Private room
  2. Chicago
SELF CHECK IN Downtown Chicago 8 minutes away
  1. Private room
  2. Chicago
Room B6
SUPERHOST
  1. Entire guest suite
  2. Chicago
Bridgeport LF Renovated Loft Studio MONTHLY
  1. Private room
  2. Chicago
5min walk to UnivOfChgo. MODERN Luxe
  1. Private room
  2. Chicago
Homey, Energy Efficient 3 & Separate Laundry Room.
  1. Private room
  2. Chicago
Room 9 Pershing Inn
  1. Airbnb
  2. United States
  3. Illinois
  4. Cook County
  5. Chicago
  6. South Side