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People skating on outdoor city rink

Dreamy Chicago Winter Experiences


Come and enjoy all the season has to offer!

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.

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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 November through March, 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, then hop on the ice! The Skating Ribbon opens on Nov. 17, 2023. 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 a Mariah Carey Christmas, Doja Cat, Disney on Ice, Madonna, The Eagles, Olivia Rodrigo and more. Located just 8 minutes from hotel.

Broadway Chicago

Broadway In Chicago

Located just 8 minutes from hotel

Broadway In Chicago is the source for terrific seats to the most exciting shows in Chicago’s bustling Downtown Theater District. On the stages of the James M. Nederlander Theatre, the Cadillac Palace Theatre, the CIBC Theatre, the Auditorium Theatre and the Broadway Playhouse, you will discover theater productions direct from Broadway and world premieres of productions destined for Broadway. Ticket prices for some Broadway shows start as low as $24. Current and upcoming productions include Hamilton, The Lehman Trilogy, A Wonderful World, Company, Samantha Bee – Your Favorite Woman: The Joy of Sex Education, Beetlejuice, BOOP! The Musical, The Illusionists – Magic of the Holidays, The Wiz, Christmas with C.S. Lewis, Hip Hop Nutcracker, Stomp,  Dr. Seuss’ How The Grinch Stole Christmas, Girl from the North Country Mrs. Doubtfire, Message in a Bottle, Pretty Woman, On Your Feet, Peter Pan, Death Becomes Her, Mamma Mia, Bluey’s Big Play, SIX, and The Kite Runner.