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Holiday rentals in Chicago

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Chicago

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

  1. Private room
  2. McKinley Park
Large Couple Bedroom w/ Queen Bed & 5min to Metro

Recently renovated, enjoy the comfort of staying on a brand-new home. Brand new mattress, comforters, sheets, towels and everything else! Each room is equipped with Smart TV with Netflix included memory-foam mattresses with 4 layers sheets & comforters bed setup, air conditioning with air humidifier, high speed internet and so much more! Easy access to public transportation. Convenient location close to downtown Chicago, Chinatown, White Sox, Pilsen, South Loop & McCormick Convention Center.

SUPERHOST
  1. Private room
  2. Near West Side
Room T5

Comfortable room furnished for short or long stays. Free, safe, and plenty parking 24/7. Located by the medical district next to little Italy, lots of restaurants and stores. Pink line five blocks away. Willis tower, Fulton market, and Greek town are all less than 9 minutes away by car. UIC is a 4 min drive. Guests can use all the common areas and appliances of the house.

SUPERHOST
  1. Private room
  2. South Chicago
Room B2

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

Holiday rentals for every style

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Other great holiday rentals in Chicago

  1. Private room
  2. Maywood
Room 4: The Maywood Manor (Twin Bed, 1 Guest)
  1. Private room
  2. Wicker Park
Simple and Convenient
  1. Private room
  2. The Loop
Downtown/Lake/Soldier Field Paradise Haven
  1. Private room
  2. Lake View
Contemporary, private suite w fireplace
SUPERHOST
  1. Private room
  2. Austin
Little Farm in the City Back Bedroom
  1. Entire rental unit
  2. East Rogers Park
Short-Term Sublet Near Lake Michigan
SUPERHOST
  1. Private room
  2. West Town
Stylish & Charming 1PBR STAYCATION SPACE For You
  1. Private room
  2. Near West Side
Cozy room in newly finished ultra modern aptmnt.
SUPERHOST
  1. Entire rental unit
  2. West Town
Great location. Free parking.
  1. Private room
  2. Irving Park
Comfortable Room Five Min Walk to Blue Line/ RM 6
  1. Private room
  2. Chicago
Private Bedroom near Downtown Chicago Chinatown
  1. Private room
  2. Woodlawn
5min walk to UnivOfChgo. Modern LUXE