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Celebrate the Holiday Season in Chicago 

Make it a memorable holiday season this year and enjoy family activities, unique Christmas markets and unforgettable attractions. Looking for things to do in Chicago in the winter? Head to Millennium Park for ice skating and caroling. Visit the top of the Willis Tower for a glittering view of the Chicago cityscape. Enjoy excellent holiday shopping at the city's landmark Macy's on State Street, and at the colorful Christkindlmarket. Celebrate the holidays in the Windy City.

Cityscape Bar

Celebrate the holidays with friends and family at Cityscape Bar. Enjoy festive cocktails and a cozy atmosphere to soak in the holiday season. Our signature holiday drink this year is the Bah Humbug cocktail. Enjoy the Bah Humbug at Cityscape Bar, and view the full recipe below!

Cocktail Recipe

Chicago Attractions

  • Millennium Park

    Visit Chicago's cultural heart this season and explore a stunning collection of architecture, art and landscape design. This winter you'll also find an ice skating rink and caroling at Cloud Gate.There's nothing quite like the holiday spirit of Chicago. Get out and enjoy the Windy City and inspiring holiday decorations.
  • Christkindlmarket

    Inspired by the traditional Christmas markets of Germany, this atmospheric shopping destination offers charm and festivities. Enjoy the open-air environment, live entertainment, unique merchandise, and authentic German food and drink. Shop for handmade gifts, meet the artists, and learn about traditional crafts.
  • Willis Tower Skydeck

    See the beautiful twinkling lights of the cityscape in red, green and silver from your perch on top of this famous skyscraper. Discover spectacular views of up to four states, along with interactive exhibits and The Ledge glass balcony. Incredible any time of year, it's even more awesome with the holiday lights.


  • Macy's

    Find the perfect gift for everyone on your shopping list at this popular department store. Also a National Historic Landmark, this flagship store features nine stories of fashion, accessories, home furnishings and cuisine. Santa and his elves will be there to delight the whole family and listen to your wish list.
  • The Magnificent Mile

    From high-end designers like Chanel and Gucci to department store favorites Bloomingdales and Nordstrom, you'll find everything you're looking for on the Magnificent Mile - a shopper's paradise.