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Walking in a Wrigley Winterland

The Cubs have turned the Friendly Confines into an amusement park and it’s magical, but bring your wallet

The sun begins to set over Winterland at Wrigley Field
Sara Sanchez

I have a confession to make, I’m generally not in the holiday spirit until well into December. I’m certainly not a grinch, but the way every holiday seems to sprawl into and before the previous one has always exhausted me a bit. Couple that with the fact that there are really only so many Christmas songs that I like and you have a perfect recipe for me to roll my eyes as the holly goes up in mid-November.

So when Al asked if I would be interested in checking out the Cubs’ new Winterland experience at Wrigley Field I fully intended to approach it with a healthy dose of skepticism. As I saw the first season ticket holder lines well down Clark Street the day before Thanksgiving, I was basically one bad rendition of Holly Jolly Christmas away from Bah Humbugging my way through this whole assignment.

But the thing is, while there are things to be skeptical about (mainly the cost of tickets — more on that below) as a whole, the experience was pretty magical. Wrigley Field is always a stunner, but it turns out Wrigley Field decorated for the holidays is a stunner in a whole different way. It begins with this view as you enter from the left field gate:

As you enter the park
Sara Sanchez

And continues with a marvelous winter baseball perfectly situated beneath the historic scoreboard in center field (yes, it’s still bugging me that there is one flag missing here). The smaller lodges below can be rented by small groups for a more private space to warm up:

The view of the center field scoreboard
Sara Sanchez

I found myself wishing my family didn’t live so far away, so I could share this experience with them, especially my cousins with small children. There are few things that would have been as wondrous to five-year-old me as riding this train around the infield at the greatest ballpark in America:

The Winterland train pulling into the station
Sara Sanchez

In addition to the train there is a Tilt-A-Whirl, tea cup rides, lots of carnival games, a slide that descends from the right field bleachers to the outfield, and an expanded ice skating rink that includes both space for skating and ice bumper cars:

A slide from the bleachers
Sara Sanchez

All of these rides will cost you some combination of tickets. While tickets were not necessary for season ticket holder day, they are necessary during regular visits to the ballpark. You can purchase a single ticket for $4, 10 tickets for $36 or 20 tickets for $69. Most rides and games are a single ticket. The exceptions are the ice rink (three tickets for access or five if you also need to rent skates) and the ice bumper cars (four tickets for one ride):

The Tilt-A-Whirl was a popular attraction
Sara Sanchez

If rides and skating aren’t really your thing, the Winterland Lodge offers a lovely place to warm up from the cold with a warm beverage. The prices are what you’d expect at Wrigley Field, so be prepared for some sticker shock, but I found it to be a cozy place to watch some highlights of the most recent Blackhawks game. A couple of concession stands were open in the concourse for food and the lodge also has a bookshelf of games for visitors to play while they enjoy their food and drink.

Two fire pits flank the lodge and you can purchase s’mores kits inside to roast marshmallows and assemble a gooey treat:

Enjoy s’mores at one of two fire pits
Sara Sanchez

With concessions for purchase and tickets adding up around every turn, it’s easy to see how an afternoon at Winterland could exponentially balloon beyond the $5 entry fee per person even before you browse the Cubs new Winterland gear or peruse the Christkindlmarket shops in Gallagher Way. With any luck, Jed Hoyer and Carter Hawkins are making plans to spend that windfall on the free agent market, so the baseball on display next spring will be at least as enticing as the amusement park on the historic field is this winter.

The carousel in Gallagher Way with Wrigley Field in the background.
Sara Sanchez