Gallagher Way Is Knocking Cold Weather Fun Outta the Ballpark

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Some Chicagoans live by the rule that there are only two seasons: winter and baseball. Baseball season has dawned on the city (there’s always next year, Cubbies!), but spending time at Wrigley Field this winter is still a fabulous way to score a home run with your kids. Once the famous chill hits, Gallagher Way at Wrigley Field becomes a wonderland, a virtual north pole right here in Chicago!  In fact, it’s actually called Winterland. This season, Winterland will take place, Nov. 19-Feb. 22. Read on and mark your calendars. . . we can promise you, the memory-making moments will not be dull. 

What is Gallagher Way?

Gallagher Way is the park right outside Wrigley Field on the west side. On game days, it acts as an entryway into Wrigley Field, as well as an area in which ticket holders can spread their legs, and watch the game on the 40-foot video screen. On non-game days and outside of baseball season, it acts as a town center with activities and events for all ages throughout the year; including free movie nights, fitness classes, musical performances, and so much more. The park is also bordered by the beautiful Hotel Zachary and several great restaurants.

Stuff Those Stockings at Christkindmarket

It opens with the return of Christkindlmarket Wrigleyville, Nov. 19-Dec. 31. Christkindlmarkets are known for their German traditions, including wooden hut structures occupied by vendors selling diverse hand-crafted gifts, scrumptious food and seasonal drink options. Make a bee-line to the raclette stand for the best melted cheese sandwiches of your life!  Also, grab a 25th-anniversary commemorative mug filled with Glühwein (hot spiced wine), or hot cocoa.

Christkindlmarket Wrigleyville hours: Mon.-Thurs., 3 p.m.-9 p.m.; Fri. & Sat., 11 a.m.-10 p.m.; Sun. 11 a.m.-7 p.m.

Special days and hours: Closed Dec. 25; Nov. 25, Dec. 24 & Dec. 31, 11 a.m.-4 p.m.

Once you’ve filled your belly and your shopping bags, head over to The Rink at Gallagher Way.  

Figure 8 Until You're Dizzy

The Rink at Gallagher Way, an 8,000-square-foot outdoor ice rink, is the focal point of Winterland, and will be open for skating, curling, and, new this year, even ice bumper car riding, for the duration of the Winterland season (weather permitting.)  

Need a skating lesson?  Starting in January 2022, The Rink at Gallagher Way will offer a six-week series of small private group lessons for ages 3 & above. Classes will be Saturdays and Sundays, 9-10 a.m. or 10-11 a.m., and are divided between beginners and more advanced skaters. The six-week session costs $100. 

Admission to the rink is free for ages 12 & under; $6 for ages 13 & over. Guests may bring their own skates or rent skates on-site for $12. Skate aids are available for $10/hour. Bags can be checked for $2.

The Rink at Gallagher Way will be open: Mon.-Thurs., 3 p.m.-9 p.m.; Fri. & Sat., 11 a.m.-10 p.m.; Sun., 11 a.m.-7 p.m.

Special days & hours: Closed Dec. 25 & Feb. 7; Nov. 25 & Dec. 24, 11 a.m.-4 p.m.; Dec. 1, 3 p.m.-5 p.m.; Jan. 17, 11 a.m.-5 p.m.

Beyond the Skates

Always wanted to try curling?  Lessons will be offered on select days in February, 6 p.m.-9 p.m. Lessons will be taught by curling professionals, and participants will learn the rules and etiquette of the sport. The cost is $50 per participant.

Space is limited for all lessons and registration begins on Nov. 1.

Looking for something a little less skillful, but equally fun? Try the new ice bumper cars, which will begin in January, and will be available Mon.-Thurs., 5 p.m.-9 p.m., Sat., 5 p.m.-9 p.m. & Sun., 3 p.m.-7 p.m. The cost is $15 for a 10-minute ride.

The Rink at Gallagher Way has also been known to host skating exhibitions throughout the winter, so stay on the lookout for those.

Settle In for Family Movie Night

If you happen to find yourself at The Rink on a Thursday evening in December, you can watch one of the free holiday movie presentations whilst you skate (or snuggle under a blanket).

Music Box Theatre will host holiday movies at Gallagher Way every Thursday in December, starting at 6 p.m. 

  • Dec. 2: National Lampoon’s Christmas Vacation
  • Dec. 9: Home Alone
  • Dec. 16: Elf
  • Dec. 23: A Christmas Story

Bundle up, grab a cocktail and get cozy while you stroll around the market, or take a little break in the warming tent, and enjoy one of these classic films!

The Fun Just Keeps Coming

Here are some other holiday highlights at Gallagher Way’s Winterland, that you won’t want to miss:

Mon., Nov. 29 — The official Tree Lighting Ceremony, accompanied by special guests, a musical performance, festive decor and the opportunity to shop, skate and enjoy concessions.

Sat., Dec. 4 & Sun., Dec. 5 (11 a.m. & 1 p.m.) — Wreath Making Workshops with local non-profit organization, Get Growing Foundation. Each instructor-led workshop is $65, benefitting the foundation.

Sun., Dec. 5 (3 p.m.-6 p.m.) — 8th Night, 8th Light, a community-wide celebration of Hanukkah, the Festival of Lights, in partnership with JCC Chicago. At sundown, the seven candles on the menorah will be lit and guests are encouraged to skate and enjoy DJ entertainment with music, dancing and trivia. Lightsticks will be passed out in the final hour of the event.

Every Fri. (3 p.m.-8 p.m.), Sat. & Sun. (11 a.m.-5 p.m.) from Nov. 26-Dec. 19 — Santa’s Workshop, (located at the base of the Cubs office building) is open to all family members, including pets on Sundays, for pictures with Santa. Professional photos will be available for purchase. 

photo: Hotel Zachary

Hop Next Door to Hotel Zachary

Still not enough to quench your thirst for holiday festivities?  Don’t worry there is even more programming available in conjunction with Hotel Zachary! 

Note, reservations are required in advance for all of the below, and will be available beginning Monday, November 1, on  They will sell out quickly!

Saturdays & Sundays (8 a.m.-11 a.m.), Nov. 27-Dec. 19 — Breakfast With Santa returns for its third year at Hotel Zachary. Enjoy a special holiday-inspired breakfast buffet, as you take pictures and have a chat with Santa by the fireplace.  This intimate setting makes for a very relaxing visit with “The Big Guy”, and great photos.  

(The holiday buffet is $35/adults & $15/ ages 4-12; pricing also includes choice of hot chocolate, coffee, tea or juice and a visit with Santa)

Sundays (1 p.m.), Nov. 28-Dec. 19 — Teddy Bear Tea invites families to enjoy a festive tea service including choice of tea or hot chocolate, with tea sandwiches and light bites, scones, cupcakes and more sweet treats. Bring your favorite teddy bear or stuffy to cuddle up with too!

(Adult tea service is available for $45/person & $25/ ages 12 & up)

Select Saturdays & Sundays (1 p.m.-1:30 p.m. & 2 p.m.-2:30 p.m.), Nov. 28-Dec. 11 — Storytime with nationally known story-performer, Chris Fascione, will charm you. Chris will be performing “Juggling Funny Stories.” Hot chocolate, cookies, snacks and hot toddies for adults, will be available for purchase a la carte.  

Those interested in attending Gallagher Way’s Winterland should follow Gallagher Way on social at @GallagherWayChi on Facebook, Twitter or Instagram.

— Debra Flanagan

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