Chicago

Friday April 25, 2025

Lindsay and I just got back from a quick trip to Chicago, and I’m very behind on work, so the previously planned theme is getting pushed for a cheap one.

With apologies to MJ Crossman, next week will be more fun. This week’s more of a recap of our quick trip.

If you want constipation, do I have something for you.

One Two Food: Deep dish pizza / Italian beef

Chicago has more hyper-local delicacies than your average city, and it’s kind of not hard to see why these things aren’t more national. They’re just… worse ways of doing already really good foods?

One of the very first things Lindsay and I did was go to Gino’s East for deep dish because I was pretty sure we’d want to just check a box and never do it again. I was right.

That said, the pizza at Gino’s East was actually really good — much better than Lou Malnati’s — but it gave us both such gastrointestinal distress that we went back to the hotel and called it a night at like 4:30. We had planned on walking about an hour to dinner that night, but we wound up ordering in because we physically couldn’t do it.

The Italian beef, which has gained new notoriety thanks to FX’s The Bear, looks like a Philly cheesesteak or steak and cheese without cheese. And that’s kind of what it is… a wet, cheeseless pile of beef and peppers on a sub roll. Al’s #1 Italian Beef was good, but I was still hungry after eating the $14 sandwich, and I found myself wondering why anyone would want a steak and cheese with inferior meat and no cheese. It made me emotionally nostalgic, wishing it were Angelo’s in Philadelphia instead.

We couldn’t handle the egg or bacon, but lettuce and tomato more than did the trick.

One Restaurant: Au Cheval

So, back to the ordering in. This was genuinely psychotic behavior. Still reeling from the deep dish, in absolutely no state to move, but knowing we had red meat plans the next two nights, we DoorDashed high-end burger joint, Au Cheval. I’m happy to report it exceeded the hype. Truly one of the best burgers I’ve ever had, and it was made better by eating it on my stomach like a bedridden otter while watching Black Mirror.

One Activity: Shoreline Sightseeing

River tours are kind of a must-do in Chicago. It’s a gorgeously built city, especially when seen from the Chicago River. Our 75-minute tour was pretty chilly, but at least the rain held off and we had some hot chocolate along the way. Our guide was entertaining enough, and she had some cool trivia, like the fact that the city reversed the flow of the river at the turn of the 20th century because they were so heavily polluting Lake Michigan. (Not for environmental reasons, but because people were dying from the shit-laced drinking water.)

This Chicago Magazine photo was coincidentally taken from our table.

One Letdown: Gibson’s Italia

When Lindsay and I travel, we basically just walk and eat. We usually make at least one fancy reservation and, on this trip, a steakhouse felt like the right move considering Chicago’s reputation as a steak town. Reddit agreed Bavette’s was the place, but I was way too late to make a reservation. So, we went with another popular Reddit recommendation: Gibson’s Italia.

The pros: Great ambiance with a dining room overlooking the confluence of the Chicago River, outstanding service, and Lindsay’s filet mignon was magnificent.

The cons: This is really my fault for ordering the pasta at a steakhouse, but Chicago’s supposed to be a great Italian food city, their gold-extruded pasta is highly regarded, and they had a vodka rigatoni. I love a vodka rigatoni! I have definitely had worse pasta in Boston, but not very often. The noodles were undercooked, the sauce was bland, and the ricotta was so extraordinarily inferior to The Little Store’s last week, I don’t really understand how they’re the same thing. Also, probably should have known better than to order a baked Alaska anywhere besides Oleana, but the baked Alaska was just fine.

Another mini bummer: The Chicago Institute of Art is randomly closed on Tuesdays so we missed it due to poor planning.

Looking at the train: Really cool. Being on the train: Fucking miserable.

One Train: The L

Great googly moogly does the L suck. Granted, taking it from downtown to Wrigley Field on a weeknight is probably the worst time to do it, but it could not have been a worse experience. We physically couldn’t fit on the first train to stop. On the second, we were packed into the middle of a completely silent car with no ventilation that had both of us dripping sweat and breathing in the skin cells of the strangers next to us. One dickhead on the car had refused to move in, so there were empty seats and like 10 square feet of just empty space and only one person weakly requested that he move in. It fell on deaf ears, and the guy dropped it to passively aggressively mutter about the rude man to his wife. I couldn’t help but think that guy would be bloody when he got off if he tried to stick with that “this is my space” bullshit in New York.

The L was slow, uncomfortable, and absolutely devoid of etiquette. Maybe Pari from Love on the Spectrum is on to something with the T.

One Game: Dodgers at Cubs

After a harrowing train ride to Wrigleyville and an okay experience at Al’s, Lindsay and I were pleasantly surprised to find Wrigleyville effectively dead. I still don’t get it. The game was sold out, our train was absolutely mobbed, but virtually every bar we saw was not anywhere near capacity. A few were completely empty. We showed up an hour before game time, but it seemed like everybody just arrived and went straight into the stadium. Like… why? It was a nice evening, the bars are cheaper, and you’re still like a 10-minute walk from your seats. Of the several odd things I noticed about Chicago and its people, this was perhaps the oddest. Why is everyone going into the stadium an hour before first pitch?

Regardless, Wrigley was a cool experience. It doesn’t really feel that old, which made it a bit boring, in my opinion. The Wrigley Rooftops behind the stadium’s outfield are really cool, but the seating is all updated, the vast majority is strung up in a single upper deck that wraps about 2/3 around the stadium and it’s pretty congested. An obese season ticket holder who showed up in the 4th screamed at us for sitting in her seats (we weren’t), and Lindsay nearly walked out of the bathroom directly into an internecine brawl. Not that these things don’t happen at Fenway, of course, but Chicagoans weren’t exactly the most impressive people throughout this trip. Weirdos on the train, horrible drivers, almost strangely aloof in restaurants and bars, and absolutely dominated by the noise of Dodgers fans in their own stadium.

Lindsay and I left before the game was over because we had an early flight, which is too bad because we missed one of the most exciting games of the year so far. After trading leads, the Cubs forced extra innings with a 2-out home run in the bottom of the ninth, only to win it on a walk-off in the 10th. We were in bed by the time the Cubs won, ready to go home.

My rankings of the baseball stadiums I’ve been to:

1. Fenway Park, Red Sox

2. Petco Park, Padres

3. Camden Yards, Orioles

4. Oracle Park, Giants

5. Dodger Stadium, Dodgers

6. Coors Field, Rockies

7. Daikin Park, Astros

8. Wrigley Field, Cubs

9. T-Mobile Park, Mariners

10. Progressive Field, Guardians

11. Angel Stadium, Angels

12. Center Parc Stadium, Braves

13. Nationals Park, Nationals