skip to main content
Chicago Bean

Dreamy Chicago Winter Experiences


Cuff It - Chicago Winter + YOU!

Whether it's a postponed holiday celebration or a visit to Chicago to break up the season, come and enjoy all the winter light has to offer in the city! No matter the temperature, there are many events, activities, and beloved traditions to enjoy this winter season in Chicago.


Spirits Lifted

You: ready to party. Us: cheering you on, big time.

Book your holiday gathering at Kimpton Gray Hotel and we’ll give every guest at your event 20% off our Best Flexible Rate on the night of the party. Plus holiday parties booked at Kimpton are even more rewarding with IHG Business Rewards. Earn points for eligible spend on your holiday party bookings.

Learn More
people ice skating

Lace The Skates

Hit one of the city’s free outdoor ice rinks. The scenic rink at Millennium Park offers panoramic views of Cloud Gate (aka “The Bean”). Open daily from November 19th through March 6th, weather permitting. Admission is free, but online reservations are required. Nearby, Maggie Daley Park is known for its one-of-a-kind skating ribbon. Admission is free—all you need to do is make an online reservation and pick up your skates.

Located just 4 blocks from hotel.

Tailor and client

Retail Therapy

Retail therapy should always be on the agenda when visiting Chicago – with several diverse shopping districts nearby. One-of-a-kind boutiques, high-end designers, outlet malls, and one of the most famous shopping streets in the world. Conveniently accessible from the hotel, once you visit Magnificent Mile, State Street, or treat yourself to luxury shopping on Oak Street you're going to need a bigger suitcase!

Broadway Chicago

United Center

Shhhh the Chicago Bulls are playing great basketball! And the United Center is celebrating 25+ years as America's premier sports and entertainment venue! Home to the @ChicagoBulls and @NHLBlackhawks. Don’t miss all the sporting action and entertainment with Disney on Ice, MUSE, and Depeche Mode among others. Located just 8 minutes from hotel.

Broadway Chicago

Broadway In Chicago

CIBC Theatre

  • Chicago the Musical (Jan 17-29, 2023)
  • 1776 (Feb 28-Mar 12, 2023)
  • A Soldier’s Play (Apr 4-16, 2023)

Cadillac Palace Theatre

  • The Lion King (until Jan 14, 2023)
  • Les Miserables (Feb 15-Mar 5, 2023)
  • Annie (Mar 7-19, 2023)
  • Aladdin (May 17-28, 2023)

James M. Nederlander Theatre

  • Dear Evan Hansen (Dec 6-Dec 31, 2022)
  • Cats (Feb 21-26, 2023)
  • Tina Turner Musical (Mar 14-Apr 2, 2023)
  • Jagged Little Pill (Apr 11-23, 2023)