We Were Already Driving Past Chicago. Obviously We Stopped.
There's a moment on every road trip where someone looks at the map and says the thing.
This time it was me. We were planning our Milwaukee trip — Reds game, a couple of days exploring the city — and I pulled up the route and just stared at it.
We were driving right past Chicago.
Right past it.
I lasted about four seconds before I started looking at hotels.
Here's how we travel: we park the car, leave it there, and wander. Walk until something interesting appears. Pop into whatever looks good. Talk to people. Get a little lost in a neighborhood and find our way back with a story we didn't plan on having.
That's not a strategy. That's just who we are.
And Wrigleyville? That's a neighborhood built for exactly that kind of wandering.
The hotel that sealed it was Hotel Zachary.
Specifically: the stadium view rooms.
I don't know what it is about seeing a ballpark from your hotel window, but it gets me every time. And this is Wrigley. One of the most iconic stadiums in all of baseball, sitting right there outside the glass.
Our team isn't playing. We are Reds fans, full stop, and we will not pretend otherwise. But here's what baseball road trippers know that casual fans don't: the stadium matters regardless of who's on the field. The history, the architecture, the neighborhood that grew up around it — that's the experience. Wrigley is worth seeing even on an off day.
We'll be seeing it from a really good room.
Also: pizza.
This is non-negotiable. Chicago pizza is its own entire conversation and we are ready to have it. Deep dish versus tavern style is still under debate in this household and honestly that discussion might carry us all the way there.
If you have strong feelings about this — and I know you do — the comments are open.
This is what Reset & Roam actually looks like: you're already headed somewhere great, and then you look at the map and realize you could also stop somewhere great, and you just... do it.
No elaborate planning required. Sometimes the best addition to a trip is the one you almost drove past.
If you're building your own baseball city trip and want help thinking through the details — the stadium, the neighborhood, where to stay, how to structure the days — The Away Game Planner was made for exactly this kind of trip.
And if you want to know how a Wrigleyville night actually goes? Check back. We'll report from the field.