Winterland at Gallagher Way welcomes family travelers back to another exciting series of festivities this year, beginning Nov. 21. This year, expect more fun than ever inside the historic Wrigley Field.

© Gallagher Way
At the entrance of Gallagher Way, visitors will find the wonderland of Christkindlmarket Wrigleyville. Throughout the ballpark, holiday décor, photo opportunities and additional rides and games await. The apres-ski-style lodge also returns to the experience, complete with unique food and beverage offerings, s’mores kits and fire pits. Families can also enjoy the return of Gallagher Ice Rink.
Those looking for the ultimate private event venue can book Winterland at Gallagher Way this holiday season, too. Winterland’s flexible spaces, including on-field private chalets, accommodate all types of celebrations.

© Gallagher Way
As Winterland nears, expect more festive happenings to be announced. Winterland at Gallagher Way runs Nov. 21, 2023–Jan. 7, 2024. Tickets are now on sale for access to the Wrigley Field portion of Winterland. Admission to Gallagher Way activities, including the Christkindlmarket Wrigleyville, is free and does not require tickets.
Attendees can also purchase the Peppermint Pack attraction bundles in advance for $30 online, while supplies last. This bundle includes Wrigley Field admission and 10 attraction tickets redeemable for all rides and games.
Read This Next
#WhereverFamily
Insta FeedHotels
Jun 15, 20263 Hotels with Standout Kid-Friendly Pools
Hotel pools get really popular during summer months, especially for families when the kids are on break from school. Not all pools are kid-friendl,y though (Vegas pool parties, for example, are one place you want to avoid at all costs with little ones!), so we’ve compiled a list of some fabulous hotels with great kid-friendly pools.
Sponsored Content
Best of Both Worlds
Enjoy the best of both worlds when you fly with TAP Air Portugal thanks to the Portugal Stopover program. With the program, TAP passengers, whether traveling for business, leisure or both, can stop in Portugal for up to 10 days at no additional airfare on the way to their final destination. What does this mean for travelers wishing to explore by both land and sea? It means after flying to Portugal with TAP and experiencing the country in an entirely new way, travelers can then embark on scenic river and ocean cruises from Portugal’s port cities, or fly with TAP to another European destination.
Cruises
Jun 15, 2026All the Ways Carnival Cruise Line Celebrates America’s 250th Birthday
This year, Carnival Cruise Line celebrates America’s 250th anniversary with special patriotic programming, and passengers are invited to take part in the festivities.
Hotels
Jun 12, 2026Saddle Up for Skillcations at These U.S. Ranches
Dude ranch vacations are growing in popularity among family travelers, but skillcation trips on ranches are also on the rise, with travelers looking for opportunities to learn a new skill and develop a new hobby while escaping day-to-day life.
Hotels
Jun 11, 2026Park Hyatt St. Kitts Launches Postpartum Experience for Moms
Park Hyatt St. Kitts now offers the perfect escape for postpartum moms to reconnect with herself in paradise through a partnership with Anya, a women’s health and beauty brand dedicated to helping with postpartum.
Hotels
Jun 11, 2026Slow Mom Summer: Family Getaways Designed for Doing Less
This summer’s biggest lifestyle trend: doing less. That mindset applies to family travel, too, with Slow Mom Summer emerging online. Moms are rejecting overscheduled itineraries and high-pressure vacations while seeking out slower, more intentional experiences.

ShareThis