Wrigleyville Entertainment Destination Welcomes Back Holiday Programming with More Family-Friendly and Interactive Experiences

Gallagher Way is thrilled to announce the return of Winterland and, for the first time since launching six years ago, the extension of the holiday experience inside Wrigley Field. The expanded programming will offer guests more family-friendly activities and new interactive experiences, along with returning favorites, including the Christkindlmarket Wrigleyville and the Gallagher Ice Rink, with the rink now located inside the iconic ballpark. Families, visitors and neighbors can celebrate the holidays by taking part in the many seasonal programs and activities starting Friday, November 18, 2022, through Sunday, January 8, 2023.

As guests enter Winterland at Gallagher Way, they’ll find themselves transported into a whimsical wonderland, including a new carousel, the return of Santa’s Workshop, additional market vendors, food and beverage offerings and even more festive happenings. The expanded experience will allow attendees to make their way through the ballpark’s Gallagher Way Gate filled with holiday décor and photo opportunities. Once they step onto the field, they’ll find new and exciting activations, including an expanded 12,000-square-foot ice rink, carnival games, ice bumper cars, the Wintertube ice slide, carnival rides, the Infield Express train and holiday music. The ballpark experience will also include a new dining option for guests, The Lodge, an après-ski style lodge featuring unique beverage offerings and firepits.

Winterland at Gallagher Way is also a premier private event destination. Adorned with jolly seasonal decorations throughout, Winterland has flexible spaces, including new on-field private chalets, to accommodate corporate holiday gatherings, intimate celebrations and more. Chalet rentals will have reservations available throughout the day accommodating up to 20 guests and will go on sale on Thursday, October 27, at 10 a.m. CT. Guests can customize their events with exclusive experiences, holiday activities, and food and beverage packages. To book a private chalet, visit

To learn more about booking private events and group experiences, visit

Admission to Gallagher Way activities, including the Christkindlmarket Wrigleyville, Santa’s Workshop and more, is FREE and requires no tickets to access the holiday fun. Christkindlmarket Wrigleyville merchandise, international food and beverage, carousel rides and photo booth pictures will be available on-site for purchase. 

 Admission to Gallagher Way activities, including the Christkindlmarket Wrigleyville, Santa’s Workshop and more, is FREE and requires no tickets to access the holiday fun. Christkindlmarket Wrigleyville merchandise, international food and beverage, carousel rides and photo booth pictures will be available on-site for purchase. 

Tickets are required for access to the Wrigley Field portion of Winterland. Regular entry tickets start at $5 (free entry for children ages 2 and under) and are subject to change. Early Bird admission and attraction tickets will be available for purchase in advance at beginning Thursday, October 27, at 10 a.m. CT. While supplies last, guests can also purchase attraction bundles in advance online, which can be redeemed for all rides and games, including the Wintertube, Infield Express and Gallagher Ice Rink activities. Admission and attraction tickets will also be available on-site for purchase. Parking information, additional ticketing information and specific pricing can be found at

Winterland Regular Hours: 

  • Monday through Thursday: 3-9 p.m. 
  • Friday and Saturday: 11 a.m.-10 p.m. 
  • Sunday: 11 a.m.-7 p.m. 

Winterland Special Hours: 

  • Thanksgiving (November 24) and Christmas Eve (December 24): 11 a.m.-4 p.m. 
  • Christmas Day (December 25): Closed 
  • Special Hours (December 26-29): 11 a.m.-9 p.m. 


The Christkindlmarket Wrigleyville at Gallagher Way opens at 11 a.m. Friday, November 18, and gives visitors the opportunity to shop for the holidays and taste traditional German and international foods while enjoying family-friendly entertainment through Saturday, December 31. 

Rooted in German tradition, the Christkindlmarket—which is always free of admission—is well known for its traditional candy cane-striped wooden huts, festive shopping options, international delicacies, hot spiced wine (Glühwein), fine beers, hand-crafted ornaments and family fun. Additional information on the Christkindlmarket Wrigleyville hours of operation can be found at


Gallagher Way invites visitors to the Gallagher Ice Rink from Friday, November 18, through Sunday, January 8, 2023, weather permitting. The Rink welcomes all skill levels to skate on their own or ride ice bumper cars on the newly expanded 12,000-square-foot ice rink, located inside Wrigley Field. 


Every Friday, Saturday and Sunday from November 25 through December 18, guests can take photos with Santa in his workshop, located in the lobby of the Premier Entrance near the Wrigley Field Marquee. Santa’s Workshop is open to all family members, including pets. Professional photos will be available for purchase. The schedule includes: 

● Friday: 3-8 p.m. 

● Saturday and Sunday: 11 a.m.-5 p.m. 

● Pets are only allowed on Sundays 



In partnership with Indigo & Violet Studio, Gallagher Way brings a festive wreath workshop to Winterland! Guests will learn how to make a fragrant, one-of-a-kind holiday decoration for all to enjoy. The instructor-led class will provide detailed instructions and wreath examples to help inspire your unique creation. Workshops will take place on Saturday, December 3, and Sunday, December 4, at 11 a.m. and 1 p.m. Tickets are $55 per person. More information on the event can be found at 


Breakfast With Santa 

Hotel Zachary’s favorite holiday tradition, Breakfast with Santa, is returning this winter season. On Saturdays and Sundays beginning November 26 through December 18, families are invited to enjoy a special holiday-inspired breakfast buffet, featuring an assortment of options for both children and adults to enjoy. 

Additional Breakfast with Santa details: 

  • Santa is available Saturdays and Sundays from 8 a.m. to noon; breakfast buffet is available from 8-11 a.m. 
  • The holiday buffet is $35 for adults and children ages four to 12 are $15; pricing also includes choice of hot chocolate, coffee, tea or juice, and a visit with Santa 
  • Reservations are required in advance and go on sale on Thursday, October 27, at 10 a.m. CT via Hotel Zachary’s Resy page 

Teddy Bear Tea 

Create warm winter memories with afternoon tea for you, your little one and their best stuffed friend with Teddy Bear Tea at Hotel Zachary. On Sunday afternoons beginning November 27 through December 18, families are invited to enjoy a festive tea service, complete with seasonal treats. Children can indulge in a pot of house-made hot chocolate, tea sandwiches and light bites, scones, cupcakes and more sweet treats. 

Additional details for Teddy Bear Tea: 

  • Available on Sundays, with seatings at 1:30 p.m., 1:45 p.m. and 2 p.m. 
  • Adult tea service is available for $45 per person and children up to 12 years of age are $25 
  • Reservations are required in advance and go on sale on Thursday, October 27, at 10 a.m. CT via Hotel Zachary’s Resy page 

Globes on the Terrace 

Cozy up on the Hotel Zachary terrace this season in the hotel’s see-through private globes, starting Friday, November 18. Those who book a globe reservation are invited to order from the hotel’s dinner menu, while sipping on a selection of seasonal beverages, like mulled house wine. The Globes offer some of the best holiday views of the bustling Winterland at Gallagher Way across Clark St., featuring a beautiful tree, the beloved Christkindlmarket Wrigleyville and more. Each globe is climate controlled and can accommodate two to eight guests total. Hours and pricing vary based on days of the week. Reservations are required in advance and go on sale on Thursday, October 27, at 10 a.m. CT via Hotel Zachary’s Tock page


Mistletoe Holiday Pop-Up Bar 

Back again for the holiday season, Mordecai’s annual holiday pop-up bar boasts naughty and nice decorations with an exclusive holiday-inspired drink menu, featuring both contemporary and vintage cocktails. Mistletoe is a limited engagement, opening Friday, November 18, through Friday, December 30. Reservations are free and can be made on Tock


Lumberjack Lodge 

This November, Smoke Daddy Wrigleyville will transform into the Lumberjack Lodge. The seasonal experience will convert the restaurant into a cozy, mountain retreat featuring special holiday food and cocktail menus and themed events, including musical bingo nights, trivia, white elephant gift exchange parties, ugly sweater parties, brunch with Santa and brunch with Buddy the Elf. For reservations and more information on the Lumberjack Lodge, please visit

For more information on this year’s Winterland festivities, follow Gallagher Way on social at @GallagherWayChi on Instagram, Facebook, TikTok and Twitter, and use the hashtag 

#WinterlandatGallagherWay or #GetTogetheratGallagherWay. 


Located in the heart of Wrigleyville and adjacent to Wrigley Field, Gallagher Way is an entertainment destination where family, friends, neighbors and visitors get together. Gallagher Way is brought to you by — and named after — Gallagher. As part of the Ricketts family’s commitment to be a good neighbor and Gallagher’s desire to contribute to the community, Gallagher Way offers year-round community programming including movie nights, an outdoor fitness series, live music, open-air markets and more. Gallagher Way offers a host of chef-driven restaurants, beautiful Hotel Zachary and is a much sought-after destination for private events. For more information about Gallagher Way, visit Follow Gallagher Way on social media @GallagherWayChi on Instagram, Facebook, TikTok and Twitter. 


Founded in 1927, Gallagher is a global insurance brokerage, risk management and consulting services firm headquartered in Rolling Meadows, Illinois. The company provides these services in approximately 130 countries around the world through its owned operations and a network of correspondent brokers and consultants. The Gallagher Way refers to Gallagher’s unique culture based on professional excellence, integrity and teamwork. For the past 90 years, Gallagher has been dedicated to developing insurance brokerage, risk management and consulting solutions for its clients, and having a positive impact in the communities in which it operates. The company also believes in maintaining a supportive and team-oriented culture in which employees can thrive and client expectations are exceeded. 


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