4 Days and 4 Nights, Chicago - Report

[Steve (from DC)]

After four days and nights, I find it easy to include Chicago as one of the world’s great cities. Whether that is measured in gleaming architecture, old commercialism, dramatic vistas, urban grime, cultural thrills, unique neighborhoods, or historic sites. There were fascinating things to see at every turn. I can’t believe it took me this long to get here.

For food, it takes a back seat to nowhere else. And it has the single most important quality I look for: Pride of Place. If Chicago is looking for a fan club president, or even a cheerleader, just hand me the pom poms and I’ll take it from there.

I don’t want to bury the lede: They’ll have to invent a new word for delicious at Birrieria Zaragoza. The ‘D Word’ just doesn’t cut it. I didn’t think I’d be able to come close after that, but I was wrong. Chicago has too much to offer.

So that was one super highlight. The super lowlight was Pequod. I can finally empathize with Ahab.

I seriously considered every suggestion I received on lthforum.com the venerable food board of Chicago. Almost everything I had was worthwhile, no comment necessary. But some items were extraordinary, so I do have some notes on those.

Here is what I ate, in chronological order. Highlights are in bold, and exclamation marks (!!) denote a super-highlight, worth the journey.

Wednesday got off to a bang.

La Chaparrita, Taco de tripa!!, taco de longaniza!!, cebollitas, alfalfa agua fresca

Kathy De’s: Breaded Steak Sandwich with homemade hot giardiniera

I got a warning about the Breaded Steak Sandwich, a true Chicago institution, perhaps not ready for the big time. ‘Like eating a shag carpet.’ Funny that, and a bit true. Triple layer of tender meat in a likeable red sauce. Maybe it was the homemade hot giardiniera that pushes it over the top? Kathy De’s does this right. It was love at first bite.

Punky’s: Chicken Vesuvio Sandwich

The first bite filled me with a hot burst of juiciness with the olive oil, white wine and garlic, The peas give it a unique touch. As with the breaded steak, the Bridgeport neighborhood near Comiskey Park is dotted with lots of places that make this.

Pleasant House Pub: Steak and ale pie!!, scotch egg!!

I have become an expert at pacing myself. And I walked off my indulgences scouring neighborhoods for the Chicago vibe. More deliciousness to follow.

[Lectroid]

Which Pequod’s did you go to, and what you didn’t care for about it?

As a Chicago native and having grown up with the original Morton Grove Pequod’s as my go to, I’m always curious when folks see things differently.

Chicago is, indeed, a real treasure trove of art, culture, and food. Not as loud about it as NYC, and not as susceptible to novelty as L.A. But it rewards a little effort.

I happen to be visiting right now as well. We had a fantastic dinner the other night at an old school red sauce Italian place called Rosebud on Taylor in little Italy. House made papardelle w. Idea sauce, and the partner had tortellini in a carbonara. And then we got to see David Byrne in concert, so a pretty fabulous night in general.

[Lectroid]

Idea sauce

I don’t know what that is, but I’d like some.

It was meant to say ‘vodka sauce’.

I’ll blame autocorrect.

[TheLibrarian28]

Thanks for the first chapter. Looking forward to more. I’ve never made it to Chicago, but this is awfully inspiring!

[Steve (from DC)]

Just like me until last week. I had no idea how phenomenal my experience would be. It’s like having your bar mitzvah and Christmas on the same day.

[Steve (from DC)]

Downtown location for Pequod. Open late and I was curious.

The crust fell apart, dough was a touch sweet, and then I got way tired of the sauce. I was fascinated by it but still regretted it.

[digga]

@Lectroid

Rosebud on Taylor in little Italy

I lived right around the corner for 3 years, followed by a year in Pilsen before it got taken over. Those were some good happy years.

I loved my time in Chicago/Illinois (6 years total, 2 in Chambana). The proverbial city of big shoulders with zero pretension. It’s been ~5 years since I last visited; I’m in early stages of planning another trip to visit a dear friend in need.

[tigerjohn]

Every time I visit Chicago, I ask myself; why am I not spending more time there, for all the reasons mentioned by previous posters.

Birreria Zaragoza and the original pequod’s are certainly part of the reason I enjoy the city so much.

[linguafood (Natascha)]

Thank you for that first report! My PIC went to grad school in Chicago and lived on the South Side for roughly 15 years. We’ve been trying to get back (it’s been a decade!), and had sorta planned a trip this fall, but we ran out of funds.

Maybe in the spring or fall of 2026

[Steve (from DC)]

Continuing on to my first full day:

Thu
Svea: Pickled Herring, Yellow Split Pea Soup

Mormors Café in the Swedish American Museum: Cardamom Roll, Almond Tart

Although the cardamom roll looks like typical viennoiserie, it had a surprising exterior crunch that made it stand out. The almond tart was in the shape of a cupcake, but the gooey, moist interior elevated this into another category.

Birrieria Zaragoza: Small Bone-in Goat Plate!!

Hard to put into words how exceptional this is. A perfect plate of heaven.

Ragadan: Basbousa Milkshake, Eggplant Ka’ak!!

After Zaragoza, I was going to be difficult to impress. But moments later, I spied the ka’ak (a bread from Jordan) at Ragadan, and I ordered the eggplant sandwich. This is one of the great sandwich breads of the world. You can also get felafel, kefta, or grilled chicken. It probably doesn’t matter because you could put footwear on this and it would be bliss.

Pequod (Downtown location): Individual pizza with green olives and mushrooms. Regretful. Enticing enough to eat more than you should. This was a throwaway late night meal, just because I could.