Chicago Day 2: Dinosaurs, Gangsters, and Deep Dish
Day two in Chicago started with a dinosaur. If you’re just joining me, start with Chicago Day One: Chicago River, the Magnificent Mile, and 550 Bottles of Whiskey.
Neither of us had been to the Field Museum before, so that was the first stop. The Field Museum sits right on the lake — big, classic, the kind of building that feels important before you even walk in, and it had a very “Night at the Museum” feel once you were inside!.
One of their biggest draws is SUE, the T-Rex. SUE has her own dedicated gallery now, 5,100 square feet with animations, interactive stations, and a recreated Cretaceous forest. One of the stations lets you smell what her breath would have smelled like. The sign said that T-Rex’s had huge gaps in their teeth where food would get stuck and rot. I decided smelling their breath was a bad idea.
We also did the T.REX 3D film, which needs a separate ticket. It’s not an IMAX-style screen — it’s fairly standard — but the show itself was well done and worth the add-on. Twenty-four minutes, and it ties in nicely with the exhibit.




Next up was Untouchable Tours, Chicago’s original gangster bus tour. They’ve been running it for over 35 years, and the meeting point is Clark Street in front of a McDonald’s. We got there a few minutes early and ended up chatting with our guide before the tour started, before she stepped into character. She goes by Marie on the tour, a nod to the Genco Pura Olive Oil Company if you know your Godfather. She mentioned she’d be singing the national anthem at Wrigley Field the following Wednesday. We were staying directly across the street.
I completely forgot to watch for her.
Still annoyed about that.
Then she became a 1920s gangster. And didn’t come back. The guides are actors, and they commit fully — voice, attitude, the whole thing. Questions get answered in character. Jokes are in character. There’s a raffle at some point where she hands out playing cards and if she draws the card you have then you get a shot glass or a book about the untouchables.
It’s a bus tour — and once you’re on, you’re on. No stops, no bathrooms, no escape. Very on-brand for a mob tour. Over the next couple of hours you’re driven past the Biograph Theatre, the St. Valentine’s Day Massacre site, Capone’s old North Side haunts, and more. If you’ve seen The Untouchables, the Biograph stop hits differently — that’s the scene.
The tone walks a line between educational and theatrical. You’re hearing about gangland executions while someone in character cracks jokes from the front of the bus. It works. Mostly. There are a couple slow stretches, but overall it’s worth it. I’d recommend the tour.


Dinner was at D’Agostino’s near our hotel in Wrigleyville — Dag’s to locals — because we really wanted to try Chicago deep dish. There had been a Cubs game that afternoon, and when we walked in the place was nearly empty. By the time the pizza arrived, the game had ended — the Cubs lost 6-3 to the Nationals, as it turned out — and the restaurant had filled right up. Cubs gear everywhere, people still replaying it. Not a celebratory crowd exactly, but an animated one. It was a fun shift to watch happen.
We were ready for the wait. Deep dish takes 30-40 minutes — that part is real.
What we weren’t ready for was the garlic. It was, without question, the garlickiest pizza either of us had ever had. We were breathing garlic for two days. Worth it.
I ordered a butterscotch Old Fashioned. Butterscotch and bourbon work in the same flavor space — caramel, brown sugar, that warm sweetness — so it’s not as odd a combination as it sounds. It was good. A bit too sweet for me to order again, but fun to try once.
Somewhere on the tour we’d started talking about The Untouchables, and by the time we got back to the Zachary it felt like the obvious way to end the day. We’d spent the afternoon on the actual streets where a lot of that story played out — a lovely way to end the day!
Field Museum is open daily 9am-5pm. The SUE 3D film needs a separate add-on ticket.
Untouchable Tours departs Clark Street between Ohio and Ontario — arrive a few minutes early, and there are no bathroom stops on the tour. Dag’s is at 1351 W. Addison.
