We Planned a Reds Road Trip. Milwaukee and Chicago Had Other Plans.
So remember when I told you Jamie, Lance, and I were road-tripping to see the Reds?
Yeah. About that.
We ended up in Milwaukee and Chicago, which is either a wrong turn or the best decision we've made all year, depending on how you look at it (I'm going with the second one).
Here's what actually happened.
The Hotel Room That Ruined Me For All Other Hotel Rooms
We stayed at the Hilton Garden Inn Milwaukee Downtown, which was lovely and fine and everything a hotel should be. But it's the second stop, Chicago's Hotel Zachary, that I need you to sit down for.
Our room looked directly out at the Wrigley Field Marquee. Not "if you lean out the window and squint." Directly. Out. At. It. Jamie caught me just standing at the window for a solid five minutes like I'd never seen a light-up sign before. I had not seen one like this before.
The view from our room at Hotel Zachary: Wrigley Field’s marquee, a sea of Cubs fans, and the exact moment I understood why people book this room on purpose.
SafeHouse: Milwaukee's Worst-Kept Secret Speakeasy
If you know, you know. If you don't: there's a password. There's a whole bit. Lance took it far too seriously and I will not be elaborating further because half the fun is not knowing what you're walking into.
What I will say is that it's exactly the kind of slightly-absurd, very-fun stop that makes a trip feel like an adventure instead of an itinerary. Ten out of ten. Bring a sense of humor.
The Bar Shuttle Wristband Incident
The Milwaukee Brat House has a shuttle that runs on a wristband system, and somewhere between brat number two and wristband logistics, this became one of my favorite unplanned parts of the entire trip. I'm not going to explain it well in one paragraph. It deserves its own post. It's getting one.
Murals, Bloody Marys, and a Bronze Fonz
Black Cat Alley is a full outdoor mural walk that I did not expect to love as much as I did — genuinely one of those "okay, Milwaukee, you're cooler than I gave you credit for" moments.
We spent way too long following painted koi fish down an alley like they’d lead us somewhere. They did not. Worth it anyway.
The Milwaukee Public Market gave us a Bloody Mary that came with what I can only describe as a full garnish buffet balanced on top of the glass. There's also a bronze statue of the Fonz on the Riverwalk, which — yes, we took the picture, no, I'm not sorry.
The Game Itself (Both Of Them)
Brewers at American Family Field, then Cubs at Wrigley a few days later — a 23-3 win for the Cubs over the Padres, in front of a crowd that stayed loud for all 27 outs. Two completely different stadium personalities, two completely different energy levels, and somehow both exactly what I needed.
So...
What I can do right now: if you want to see Milwaukee and or Chicago, I can book the exact hotels we stayed in — same Hilton Garden Inn, same Hotel Zachary marquee view if it's available — no group required.
Email me at tracy@harmonyhorizon360.com and I'll get you set up.
If enough of you want to do this together down the road, exactly as we did it? That's where the group trip lives. For now: go see it and tell me how it goes.
Related Posts:
See where it started: Taking Our ND Son to Milwaukee — Here’s How We’re Planning It Differently — Harmony Horizon 360 Travel
See other Baseball City Trips: Cincinnati Reds Game Day Trip: Brunch, Breweries, and a Loss We're Still Processing — Harmony Horizon 360 Travel
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.