Combine a love of baseball with the holidays and plan family travel to Chicago, as Gallagher Way announces the return of Winterland and an extension of the holiday experience inside Wrigley Field. With the expanded programming comes more family-friendly activities, festive décor, interactive experiences, rides and more.
Returning favorites include the Gallagher Ice Rink, which will be inside the ballpark; Santa’s Workshop; a tree lighting ceremony; and special programming at Hotel Zachary and select nearby restaurants. Seasonal programs and activities begin Nov. 18, and run through Jan. 8, 2023.
The Christkindlmarket Wrigleyville returns to Gallagher Way, and also opens Nov. 18. Visitors can shop and enjoy German and international foods, alongside family-friendly entertainment, all through Dec. 31.
In Winterland, host corporate holiday events, family parties, intimate celebrations and more. Events are completely customizable, and can include exclusive experiences, holiday activities and food and beverage packages — all set against a backdrop of seasonal decorations.
Right in the heart of Wrigleyville, adjacent to Wrigley Field, Gallagher Way, an entertainment destination, delivers year-round community programming for family, friends, neighbors and visitors. Enjoy movie nights, an outdoor fitness series, live music, open-air markets and much more.
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