Start Somewhere That Means Something — Wrigley Field, Chicago

Finding the right gift for a sports-obsessed husband is both easy and impossible. Easy because the universe of options is enormous. Impossible because he already has everything, follows everything, and has strong opinions about all of it.

Jon loves baseball and football. He runs fantasy leagues. He follows players I’ve never heard of. Doing all 30 MLB parks together was something he and his dad always talked about. His dad, Larry, passed away ten years ago — before they had the chance.

So when an ad for a laser-engraved wooden baseball stadium bucket list board popped up on Etsy — all 30 MLB stadiums with a little slot for each team token — I jumped on it.

Then I bought Cubs tickets. Jon’s an Angels fan, and the Angels were coming to Wrigley.

I wrapped the board separately from the tickets and tucked the Cubs token in with the envelope. He opened the board first, then the tickets. It took about two seconds to put it together. Park number one: Wrigley Field.

Am I committing us to seeing all 30 MLB parks? Apparently yes. This may take years. I’m choosing to see this as a feature, not a bug — a ready-made excuse for trips to cities we might not otherwise visit, each one with its own story. This is the first in what will be a long and occasionally delayed series.

Why Wrigley

About a month before Christmas I called Rick, Jon’s brother, to figure out where to start. Rick knows baseball. We went through the options and landed on Wrigley. It’s iconic. It’s historic. It opened in 1914 and still feels like it belongs to a different era of the sport. If you’re going to start a stadium bucket list, you start somewhere that means something.

Hotel Zachary

I chose Hotel Zachary deliberately. Jon is the sports fan — this whole trip was for him — and I wanted the experience to be fully immersive from the moment we arrived. Hotel Zachary sits directly across the street from Wrigley Field, in the heart of Wrigleyville. You don’t just go to the game. You live in it for a few days.

The hotel is named after Zachary Taylor Davis, the architect who designed Wrigley Field in 1914. His wife was named Alma — which is also the name of the bar on the second floor, a terrace bar with a direct view of the field. On the wall inside hangs a framed print of the original blueprint. Jon noticed it immediately. I noticed the cocktail menu.

The Consolation Prize

I couldn’t get a nonstop flight on Delta from Orlando and we were using Delta points, so we had to go with connecting flights. Weather delays hit both legs. We sat in airports. We waited. By the time we landed in Chicago and made it to the hotel it was nearly 8pm, and our 7:15 reservation at Gibsons (the steakhouse ChatGPT had recommended) had to be cancelled.

So we switched gears and went to Alma. Fried chicken sliders — perfectly crunchy, lighter than expected, genuinely good. And I ordered the Zachary Old Fashioned.

The drink is made with Koval Hotel Zachary Private Barrel Bourbon — a custom barrel sourced specifically for the hotel — smoked sugar, and Alma’s own private bitters blend. I’d wondered about the smoked sugar. Turns out bartenders typically infuse sugar with smoke using a smoking gun or by letting it absorb smoke in a sealed container with wood chips. The result carries a deep, woodsy undertone without losing its sweetness. In the glass it translated to a smokiness that lingered without overpowering — not a campfire, not ashes, just a warm quiet backbone underneath the bourbon that made every sip an experience.

I also tried the Alma Old Fashioned, which swaps in a tequila-based reposado and agave. It was genuinely lovely.

But I’m a whiskey girl and the Zachary was something else entirely. It is tied for the best old fashioneds I’ve ever had, sharing that title with one I had at Bourbon Steak in Orlando. Two completely different drinks, both exceptional. The fact that I found this one at the end of a long day of weather delays and cancelled dinner reservations made it better, not worse.

Sometimes the detour is the destination.

Alma at Hotel Zachary is located at 3630 N Clark St, Chicago, IL 60613, on the second floor. Reservations recommended on game days. We never got to Gibsons but ChatGPT highly recommended it! Hotel Zachary is a Marriott hotel for those of you who are Marriott members.

Up Next

Up next: Day one. A river cruise, the Magnificent Mile, and an underground speakeasy sitting on the largest collection of American whiskey in the world. Chicago was off to a good start before we even made it to the ballpark.