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Vacation rentals in South Side

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in South Side

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

  1. Private room
  2. Chicago
Self Check-in 8 min Downtown Chicago

This stylish place to stay is perfect for guests looking to have a great airbnb experience. Recently renovated, enjoy the comfort of staying on a brand new home with everything brand new. Brand new mattress, comforters, sheets, towels and everything else! Each room is equipped with Smart TV with Netflix, Amazon Videos and 300+ TV channels included, expensive luxury mattresses with 4 layers sheets & comforters bed setup, air conditioning with air humidifier, high speed internet and so much more!

  1. Private room
  2. Chicago
BRONZEVILLE OASIS II- 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. Private room
  2. Chicago
Room B2

Cozy private room with Ac. Common areas such as bathroom and kitchen Antea all brand new.

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Other great holiday rentals in South Side

  1. Private room
  2. Chicago
Luxury BR w/private bath 4mins to Univ & Hospital
  1. Private room
  2. Chicago
Master Bedroom in Spacious and Comfy Chicago Condo
SUPERHOST
  1. Private room
  2. Chicago
Downtown Chicago 8 minutes away SELF CHECK IN
SUPERHOST
  1. Private room
  2. Chicago
Luxury Stay near Downtown Chicago New Queen bed
SUPERHOST
  1. Private room
  2. Chicago
B5Hotel quality room near Downtown, CTA,McCormick
  1. Private room
  2. Chicago
Homey, Energy Efficient 3 & Separate Laundry Room.
  1. Private room
  2. Chicago
Private Bedroom near Downtown Chicago Chinatown
SUPERHOST
  1. Private room
  2. Chicago
Cozy guest room 1 block from U of C
  1. Private room
  2. Chicago
Rustic Private BR - 5 min to Chinatown & Downtown
SUPERHOST
  1. Private room
  2. Chicago
10min to UIC, 5min to Sox Field and Soldier Field
  1. Private room
  2. Chicago
Self Check-in 8 min Downtown Chicago
SUPERHOST
  1. Private room
  2. Chicago
Room B3