Hero Image

The best holiday activities in Chicago

The Best Holiday Activities in Chicago are at Hotel Zachary

Hotel Zachary invites guests throughout the holiday season to cozy up near the fireplace and indulge in a variety of festive menu items, including a selection of Hot Toddy's and complimentary Christkindlmarket mug refills. These serve as the perfect complement to Winterland at Gallagher Way, with attractions including the Christkindlmarket, an ice rink, a stunning holiday tree and Santa's workshop. 

Visit Christkindlmarket Wrigleyville in Gallagher Way all season long

The smell of roasted nuts, fresh pretzels, bratwurst, hot spiced wine, combined with the sound of music and the glimmer or sparkling Christmas ornaments, all in a cozy atmosphere - this is the authentic German-style Christkindlmarket experience.

Visitors can shop products from all around the world and enjoy the unique atmosphere while enjoying international food, beverages and performances at the outdoor market that is always free of admission. 

More Information

Enjoy Teddy Bear Tea at Hotel Zachary

Create new and warm winter memories with high tea for you, your little one and their best stuffed friend with Teddy Bear Tea at Hotel Zachary. On Sunday afternoons beginning November 28 through December 19, 2021, Hotel Zachary welcomes families to enjoy a festive tea service featuring Rare Tea Cellars. With seatings at 1 p.m. children can indulge in a pot of house-made hot chocolate, assorted tea sandwiches and delectable sweet treats before a special guest storyteller arrives.

WHEN: Sundays, November 28 through December 19, 2021 with seatings from 2-3 p.m.

PRICING: Adult tea service is available for $55 per person and children ages two to twelve are $35

RESERVATIONS: Reservations are required in advance and will be available beginning November 1

Book Your Tea Service Today

Breakfast with Santa at Hotel Zachary

Guests can start a new holiday tradition with Breakfast with Santa at Hotel Zachary. On Saturdays and Sundays beginning November 27 through December 19, 2021, families are invited to enjoy a special holiday-inspired breakfast buffet featuring an assortment of upscale options for both children and adults to enjoy, while Jolly Old Saint Nick relaxes near the fireplace, waiting to visit with good boys and girls, and listen to their holiday wishes. Reservations are recommended in advance and will be available beginning November 1.

WHEN: Saturdays and Sundays beginning November 27 through December 19, 2021, from 8 a.m. - 11 a.m.

PRICING: Adults for $50 per person. Children ages four to twelve are $20.

Book Your Breakfast With Santa Today

Ice Skating, Curling, Santa’s Workshop and more!

  • Ice skate with Santa and figure skaters

  • Learn to skate or curl

  • Visit Santa’s Workshop

  • Craft a perfect holiday wreath

  • Enjoy a favorite holiday movie

View All Holiday Events at Gallagher Way