Celebrate the season with holiday events in Chicago

Celebrate the holiday season at Gallagher Way, just steps away from iconic Wrigley Field. Get into the holiday spirit with a spin on the ice, a seat on Santa’s lap, a seasonal movie or any of our other holiday and winter events.

That’s just the start — check back often to see what other Chicago festivities are happening at Gallagher Way.

Our ice skating rink takes fun holiday events outdoors

Enjoy a new family tradition, a moment with someone special or a place to practice your ice skating skills on our ice rink, located right outside Wrigley Field. This holiday event is family-friendly and free admission for anyone under 12 years old.

Santa joins our skaters every Thursday

Skate with Santa November 29 – December 20 from 4:30 – 6:30 p.m. Share your holiday wishes and take a great picture in the process! You can also learn new moves from Figure Skate Chicago’s youth performances every Wednesday, November 28 – December 19 from 6 – 6:15 p.m.

Download and print the Winterland PDF calendar

Come Skate with Clark the Cub

Clark the Cub also will be making his skating appearances November 24 and December 1 from 11:30 a.m. – 1 p.m.

Hours & Pricing

Guests may bring their own skates or rent on site. Skate aids, to assist the littlest skaters, and bag check are also available at the skate rental.

Monday – Thursday 3 – 9 p.m.

Friday – Sunday 11 a.m. – 9 p.m.

Children (12 yrs & under)Free

Admission (13 yrs & older)$5

Skate Rental$10

Bag Check$2

Skate Aid$10

Adult 10-Skate Pass$130

Children’s 10-Skate Pass$80

Download and print the Winterland PDF calendar

Special Holiday Hours

December 24 & 2511 a.m. – 5 p.m.

December 26 – January 411 a.m. – 9 p.m.

January 2111 a.m. – 4 p.m.

Want more time on the ice? Learn to skate, learn to curl or rent the whole rink for a private event

Sign up for our six-week Learn to Skate class (SOLD OUT)

Our ice rink offers classes for beginner skaters and curious curlers. Get comfortable on the ice with Learn to Skate classes every Saturday or Sunday for six weeks from 9 – 11 a.m.


Learn to curl like an Olympian (SOLD OUT)

Join us for Learn to Curl classes, available January 8 – 10 and 22 – 24. Each date will include three sessions each evening with room for 16 curlers per session, taught by Chicago Curling Club, Windy City Curling Club, Second City Curling Club and Exmoor Curling Club. Classes cost $50 and include a beverage of your choice afterwards at Smoke Daddy Wrigleyville.

SOLD OUT! Join the waitlist.

Chimes at Gallagher Way

New this winter season, the “Chimes at Gallagher Way” are a modern and surprising interactive art installation designed to demonstrate the chaos theory, in which a very small change in the system results in a large difference in time. 

A random disorder of 30 lights and eight speakers will spring to life with the slightest sway of the chimes in Gallagher Way. A simple gust of wind or interaction from guests will transform the entire ambiance and create a distinctly unique light show and aural motif. Every chock between the chimes’ bells disturbs the audiovisual environment and will generate divergent evolutions. This is the first U.S. chimes installation, co-produced by Illuminart (Montreal, Canada), Quartier des Spectacles Partnership (Montreal, Canada), Fête des Lumières (Lyon, France) and Collectif Blackbox (artist).


Monday – Thursday3 – 9 p.m.

Friday – Sunday11 a.m. – 9 p.m.

Download and print the Winterland PDF calendar

Special Holiday Hours

December 24 & 253 – 9 p.m.

December 26 – January 43 – 9 p.m.

January 2111 a.m. – 9 p.m.

Enjoy a classic Christmas moment at Santa’s Workshop

Santa’s Workshop

Every Friday, Saturday and Sunday from late November through Christmas, take your photos with Santa at Gallagher Way, located outside of Wrigley Field. Santa’s Workshop is open to all family members including your pets. Each Sunday, your cats and dogs can get their time with Santa at our “Santa Paws” events. Professional photos will be available for purchase.

Santa’s Workshop Hours

November 23 – December 23

Friday3 – 8 p.m.

Saturday – Sunday11 a.m. – 5 p.m.

Download and print the Winterland PDF calendar

Satisfy the craftiest maker with these Chicago holiday activities (SOLD OUT)

We’re partnering with two Chicago organizations to bring you festive one-of-a-kind holiday decor during our wreath making classes: Chicago Flower & Garden Show and Get Out & Grow. Together, we’re hosting three wreath making classes at the American Airlines Conference Center located at 1101 W. Waveland, next to Wrigley Field. This event is sold out!

Class Hours & Pricing


Dec 2, 9, 16noon – 1:30 p.m.

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Adults (18 and over)$25

Minors (17 and younger)$15

Watch your favorite holiday movies on the big screen next to Wrigley Field

Join us on select Friday nights in November, December and January for screenings of our favorite holiday and seasonal movies on the Gallagher Way video board. And don’t worry about the weather — you can watch while skating, bundled up with a hot chocolate or cozied up at one of our neighboring restaurants. See below for the full holiday movie calendar:

All movies start at 6 p.m.

Download and print the Winterland PDF calendar


Nov 23

Home Alone

Nov 30

Love Actually

Dec 7

A Christmas Story

Dec 14

National Lampoon’s Christmas Vacation

Dec 21

The Holiday

Dec 28


Jan 4

Looking to host your winter event in Chicago?

Consider renting out the entire ice rink for an unforgettable experience.

  • Rental includes admission, skates, bag check and skate aids
  • Special group pricing during public hours
  • Food and beverage packages available at any of the surrounding Gallagher Way restaurants

Get in Touch

Treat your family to Breakfast with Santa or Teddy Bear Tea

We have the perfect family events to bring a moment of magic to the holidays!

Breakfast with Santa (SOLD OUT)

Start your day at Hotel Zachary for breakfast with Santa. On select Saturdays in December, bring out the whole family dressed in their holiday best for a full breakfast in Hotel Zachary’s lobby and Alma Room. Good girls and boys who finish their meal can visit St. Nick by the fireplace and decorate their own holiday cookies.

Breakfast with Santa Hours & Pricing (SOLD OUT)

  • $20 prix fixe menu includes juice, coffee and one breakfast option from our a la carte menu. Add an extra $12 for the special beverage buffet of hot chocolate and juices for children age 2-12. Children under 2 years old eat free.
  • December 8, 9, 15 and 16 from 8-10 a.m.
  • Specialty breakfast cocktails are available for purchase

Teddy Bear Tea

Children of all ages are invited to sip on tea with their favorite stuffed animal by their side at Hotel Zachary. The Alma Room will be decked out in a Toyland theme, with classic toys and cuddly teddy bears. Adults and children may enjoy a full tea service, which includes a list of specialty teas and drinks, a three-tier tower of pastries and other surprises from West Town Bakery. After the kids finish their tea, they can head into the Fireplace Room for storytime while the adults finish their own treats.

Teddy Bear Tea seatings are available at 11 a.m., 1 p.m. and 3 p.m. on the following dates:

November 24 – 25, December 8, 9, 15, 16 and every day December 22 – 30.

Book your Tea Today!

For Those 21 Years Old & Older

Stop by Hotel Zachary and cozy up near the fireplace with traditional and modern takes on the hot toddy – brought to you by Beam Suntory. The seasonal drink menu will be available during the month of December from 11 a.m. to close every day.

Hotel Zachary

During its inaugural holiday season, Hotel Zachary will be a must-visit destination for neighbors, families and tourists. Stunning holiday décor and weekend activities such as Breakfast with Santa, Teddy Bear Tea and other holiday activations will take place all winter long.

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Private Events at Gallagher Way

Gallagher Way and its surrounding restaurants are available for private event bookings of all sizes, all year long.

Want to Learn More?

Get in Touch

Winterland FAQs

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