Chicago Day 3: Cheezborgers, Ice Cream, and Wrigley Field
If you’re just joining me, this is the third day of a trip to Chicago to see the Angels vs the Cubs. The first post in the series is here: You Start Somewhere That Means Something — Wrigley Field, Chicago.
Jon woke up excited. Everything else this trip — the architecture cruise, the whiskey, the dinosaurs, the gangsters, the deep dish — had been great, but it was all leading here. On game day at Wrigley Field, where he stood was somewhere between a kid on Christmas morning and walking down Main Street at Disney World — which, if you know Jon, are both his happy place.
We didn’t have anywhere to be until first pitch at 6:40, so the afternoon was ours. We intentionally left the day free so we could explore Wrigleyville.
Wrigleyville Before the Game
Wrigleyville has its own ecosystem. The streets around the stadium have bars, restaurants, and shops that exist entirely in service of the Cubs. There are rooftop buildings directly across from the outfield — the Wrigley Rooftops — where people pay to watch the game from lawn chairs above a bar. Home run balls occasionally land in the street. It’s the kind of neighborhood that has been shaped entirely by the thing at its center.
We walked past the Billy Goat Tavern. It had a sign saying it was famous but we’d never heard of it. A quick Google came up with an SNL sketch — cheezborger cheezborger cheezborger, no fries cheeps, no Pepsi Coke — but the Billy Goat is also the origin of the Curse of the Billy Goat, the reason the Cubs didn’t win a World Series for 108 years. The owner was turned away at the gate for trying to bring his goat to a game, and the rest is lore. A lot of history packed into a pretty small bar.
We stopped into Obvious Shirts, which is a Chicago t-shirt shop near the park. I got a Wrigley shirt. Jon got a few shirts and a cap that I don’t fully understand, but he was happy.
Jon spent the afternoon in his Angels gear lightly needling Cubs fans and calling out to Angel’s fans when they walked by. I was guilted into wearing an Angels cap for the game — I do not look good in baseball caps. I explained this to Jon but got no sympathy at all!
Gallagher Way and Jeni’s Ice Cream
Just outside the park is Gallagher Way — a plaza that opens up before games and takes on a whole pre-game energy of its own. People were tossing balls around when we got there. We grabbed ice cream from Jeni’s, found a table, and sat watching. Jon was happy. That’s the thing about being at Wrigley with an actual baseball person: the pre-game warmup, the smell of the field, people throwing a ball around in a plaza — all of it registers. None of it was lost on him.
Alma, Round Two
Before heading over to the park we went back upstairs to the terrace at Alma — our hotel bar with the direct view of the field — for a Zachary Old Fashioned. If you read the first post in this series, you know how much I loved this drink and I wanted to see Alma in the daytime. We sat on the terrace and watched the stadium fill up and soaked it all in.
Catalina Club
The tickets were a Christmas present, so I had splurged. ChatGPT will tell you that if you want the authentic Wrigley experience you should sit in the bleachers — old wooden benches, full sun, among the diehards. That is not how my husband rolls. So: Catalina Club.
The Catalina Club sits in sections 315-318, just behind home plate in the upper level, with a panoramic view of the whole field. It’s all-inclusive — food, beer, wine — with nicer seats, private restrooms, and an indoor club lounge that has sightlines out to the field. Sliders, hot dogs, a buffet line, and a freezer full of ice cream! Nothing wrong with two ice creams on the same day right?
They were handing out commemorative opening day caps and at the seventh inning stretch, the whole park sang Take Me Out to the Ballgame. On our first day in Chicago, we stumbled onto the Harry Caray exhibit at the Chicago Sports Museum — the legendary Cubs announcer who made that tradition what it is. There’s something about 40,000 people singing that song, in that park, that gets you whether you’re a baseball person or not.
The Cubs won.
Jon is an Angels fan.
Ah well.
Back Across the Street
One of the genuinely great things about Hotel Zachary is that when the game ends you walk across the street and you’re done. No transit, no Uber, no parking situation to navigate. We walked back and called it a night. Jon put the Cubs token in the board when we got home.
Park one: done. Twenty-nine to go.
Jeni’s Splendid Ice Creams has multiple Chicago locations including one near Wrigley. Gallagher Way is the plaza just west of the park — open year-round, worth a wander on game day. Catalina Club seating is available through the Cubs ticketing site; for a first visit it’s a great splurge. Wrigley Rooftops are across Sheffield and Waveland Avenues.
