71.4 F
Sponsor Message

Chicago’s Gallagher Way Gets Decked-Out for Winterland this Holiday Season


This article is more than 5 years old and may not have been updated since our last site redesign. It may contain outdated information or could be missing images.

Wrigleyville’s Gallagher Way continues to be a growing destination for families in Chicago, and this holiday season, the festive activities are bigger and more plentiful than ever.

Winterland programs at Wrigleyville hot spot begin on Nov. 22, and run through Feb. 16, 2020.

This year, Christkindlmarket Wrigleyville returns alongside an 8,000-square-foot ice rink, curling and skating lessons, Santa’s Workshop, wreath making classes, oversized decorative winter characters, holiday movies and more. The holiday transformation will also include a 30-foot holiday tree underneath the Wrigley Field Marquee, a tree lot at Big Star Wrigleyville, holiday programming at Hotel Zachary, Hush Money, Lucky Dorr, Smoke Daddy Wrigleyville and other restaurants around Gallagher Way, plus a dazzling display of decorative lights around Gallagher Way.


The Rink at Gallagher Way invites visitors to take the ice November 22 through February 16, weather permitting. The Rink at Gallagher Way welcomes all skill levels to skate on their own, participate in skating lessons, enjoy figure skating exhibitions and learn to curl.

Clark the Cub will make his skating appearances on select Wednesdays in December.

Admission is free for skaters 12 years and younger; $6 for skaters 13 years and older. Guests may bring their own skates or rent skates on-site for $12. Skate aids are available for $10 per hour. Bags can be checked at the skate rental for $2.

The Rink at Gallagher Way will be open:
Monday through Thursday: 3-9 p.m.
Friday and Saturday: 11 a.m.-10 p.m.
Sunday: 11 a.m.-7 p.m.

Special Days & Hours:

  • November 28: 11 a.m.-4 p.m.
  • December 23, 26, 30, 31: 11 a.m.-9.p.m.
  • December 24: 11 a.m.-4 p.m.
  • December 25: CLOSED
  • January 1, 2, 20: 11 a.m.-9 p.m.

Christkindle Wrigley


The Christkindlmarket Wrigleyville at Gallagher Way will open November 22, and will give visitors the opportunity to shop for the holidays and taste traditional German and international foods while enjoying family friendly entertainment through 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.

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.

Special Hours:

  • Thanksgiving (November 28), Christmas Eve (December 24) and New Year’s Eve (December 31): 11 a.m.-4 p.m.
  • Christmas Day (December 25): Closed


Every Friday, Saturday and Sunday from November 29 through December 22, guests can take photos with Santa in his workshop located in Wrigley Field’s Premier Lobby near the Marquee Gate. Santa’s Workshop is open to all family members including pets. Professional photos will be available for purchase.

Fridays: 3-8 p.m.
Saturdays and Sundays: 11 a.m.-5 p.m.*
*Please note, pet photos will only be available on Sundays.


Starting January 4, guests three years of age and older can learn to ice skate with small private group lessons. The hour-long, six-week course will run through February 9.

Ice skaters can select either Saturday or Sunday lessons from 9-10 a.m. or 10-11 a.m. Participants can learn basic skills like two-foot turns and skating forward, while more advanced skaters will learn forward and backward cross overs and edge work. Make-up classes will be offered February 15 and 16, weather permitting.

Lessons cost $100 for six weeks. Participants will receive discounted skate rentals at $5 per lesson. Space is limited.


A figure skating exhibition will be on Tuesdays, starting November 26 through December 17, from 6-6:15 p.m.


Gallagher Way will host a tree lighting ceremony and toy drive to kick off the holiday season December 2. Fans and neighbors are welcome to gather for an evening filled with holiday cheer followed by the official tree lighting. After the ceremony, guests can enjoy shopping at the Christkindlmarket Wrigleyville and skating on the ice with Clark the Cub.


Guests can learn how to curl by signing up for hour-long classes taught by curling professionals January 7-9 and January 21-23, from 6-9 p.m. on select dates in January. Participants will learn the rules and etiquette of the sport before “sweeping” to a victory. The cost is $50 per participant. Learn to curl classes are offered for guests ages eight and older.


Guests can watch classic holiday movies at Gallagher Way every Thursday in December starting at 6 p.m.

  • December 5: Elf
  • December 12: National Lampoon’s Christmas Vacation
  • December 19: Home Alone
  • December 26: The Cutting Edge


Starting November 29, City Tree Delivery, Inc. will return for its 10th year as a full-service Christmas tree business with a tree lot located next to Big Star Wrigleyville at 3640 N. Clark St. Customers can purchase premium Fraser Fir trees, wreaths, garland and accessories, as well as order online tree delivery, tree setup and tree removal. For more information, hours of operation or to place an online order, please visit www.citytreedelivery.com.


Guests can start a new holiday tradition with Breakfast with Santa at Hotel Zachary. On Saturdays and Sundays beginning November 30 through December 22, families are invited to enjoy a special holiday-inspired breakfast buffet featuring assorted pastries and bread, yogurt parfaits, scrambled eggs, biscuits and gravy, white chocolate peppermint pancakes, an omelet station and more, while Santa relaxes near the fireplace, waiting to visit with good boys and girls, and listen to their holiday wishes.

Additional Breakfast with Santa details follow:


  • Santa is available Saturdays and Sundays, November 30 through December 22, from 8-11 a.m.; breakfast buffet available from 6:30-11 a.m.
  • The holiday buffet is $60 for adults and includes one mimosa. Children ages two to 12 are $20. Pricing also includes choice of hot chocolate, coffee, tea or juice, and a visit with Santa
  • Reservations are recommended in advance and will be available beginning Friday, November 1, at Resy.com



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 Saturdays and Sundays beginning November 30 through December 29, the Alma Room welcomes families to enjoy a festive tea service featuring Rare Tea Cellars. With two seatings, 11 a.m. and 1:30 p.m., children and adults can indulge in a pot of house-made hot chocolate, assorted tea sandwiches and delectable sweet treats before a special guest storyteller arrives.

Additional details for Teddy Bear Tea follow:

  • Saturdays and Sundays, November 30 through December 29, at 11 a.m. and 1:30 p.m.
  • Adult tea service is available for $55 per person and children ages two to 12 are $35
  • Reservations are required in advance and will be available beginning November 1, at Resy.com




In partnership with two local Chicago organizations, Chicago Flower & Garden Show and Get Growing Foundation, Gallagher Way brings festive one-of-a-kind holiday decor during its wreath making and decorating classes at the American Airlines Conference Center for all to enjoy

  • December 1, 8 and 15; 11 a.m.-12:30 p.m. and 1-2:30 p.m.
  • $50 for adults 18 years and older


All winter long, the Rink at Gallagher Way, American Airlines Conference Center, Hotel Zachary and the surrounding restaurants are available for private event bookings of all sizes. Additional details on booking a private event at the Rink at Gallagher Way are as follows:
  • Private rental to include up to 250 guests
  • Rental includes admission, skates, bag check and skate aids
  • Special group pricing for groups of 15 or more during public hours
  • Food and beverage packages are available in the American Airlines Conference Center and Gallagher Way restaurants
The Debut of the RUN DMC x Igloo Cooler Collection | Shop Now

Recent Stories:

Sponsor Message

The Toy Book:

Sponsor Message

Rock Father Rides:

Sponsor Message
Entertainment Earth
Sponsor Message
Sponsor Message Fandango Gift Cards