Skip to content

Holiday rentals in Chicago River

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Chicago River

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

  1. Hotel room
  2. Chicago
Hotel Perks - Private Bedroom | Private Bathroom

Freehand Hotel is great for couples, solo adventurers, and business travelers. Experience the comfortable and casual vibe designed by Roman & Williams in River North Chicago, just two blocks from the Magnificent Mile. Walking distance to public transportation, Navy Pier, and more. $10 nightly resort fee plus tax paid at the property For long-term stays, guests must move rooms about every 30 days.

SUPERHOST
  1. Private room
  2. Chicago
SHARED Artist Loft . Very Unique

Beautiful SHARED artist loft space with elevated, open bedroom with curtains. Located on the top floor of a building built in the early 1900s, enjoy a unique experience in the heart of River North/downtown Chicago. Our One-of-a-kind rooftop garden is a must-see during Summer/early Fall. This space is ideal for socializing. NOTE: Includes five-story walkup, NO ELEVATOR ALREADY BOOKED??? If this room is unavailable, check out my profile to see our other listings! Feel free to message me!

SUPERHOST
  1. Entire rental unit
  2. Chicago
Millennium Park Paradise (2BD/2BA)

Located in Chicago's Loop, this large 2 Bedroom is in the heart of all things Chicago. Theatres, shopping, great restaurants, nightlife, parks and Lake Michigan are all nearby!

Holiday rentals for every style

Get the amount of space that is right for you.

  • Homes
  • Hotels
  • Unique stays

Stay near Chicago River's top sights

Photo of Chicago Architecture Center
Chicago Architecture Center73 locals recommend
Photo of The Chicago Theatre
The Chicago Theatre36 locals recommend
Photo of DuSable Bridge
DuSable Bridge9 locals recommend
Photo of The Wrigley Building
The Wrigley Building5 locals recommend
Photo of House of Blues Chicago
House of Blues Chicago29 locals recommend
Photo of Trump International Hotel & Tower® Chicago
Trump International Hotel & Tower® Chicago16 locals recommend

Other great holiday rentals in Chicago River

  1. Entire guest suite
  2. Chicago
Cozy one-bedroom suite in the heart of West Loop
  1. Entire rental unit
  2. Chicago
Beautiful Condo in Chicago
  1. Entire apartment
  2. Chicago
lux furnished condo with A+++ view in River North
  1. Entire rental unit
  2. Chicago
1-bedroom unit with a bird-eye view
  1. Entire apartment
  2. Chicago
Spacious 1BR apt 2 blocks from Michigan Ave
SUPERHOST
  1. Entire rental unit
  2. Chicago
GREAT Downtown UNIT 24/7 GYM +TV Netflix WIFI
  1. Entire rental unit
  2. Chicago
Great Location @TheLoop close to #ChicagoTheatre
SUPERHOST
  1. Private room
  2. Chicago
Private Bedroom w/ bath in Chicago Downtown/Loop
SUPERHOST
  1. Private room
  2. Chicago
SHARED Artist Loft, Private Room
SUPERHOST
  1. Private room
  2. Chicago
Chicago Speakeasy-Style Loft Space (Room 4A)
SUPERHOST
  1. Entire rental unit
  2. Chicago
Highrise Haven (2BD)
PLUS
  1. Entire rental unit
  2. Chicago
Urban Chic Apartment by the Magnificent Mile
  1. Airbnb
  2. United States
  3. Illinois
  4. Cook County
  5. Chicago River