The 5 Best Things I Ate in Chicago

In this series, I round up the five best things I ate in a particular city or country. Click here to read previous 5BTIAs from Paris, London, and more.

You guys. Why has no one told me about Chicago? Or I suppose more accurately: why has no one insisted I go to Chicago?!

It took 29 years of flying through O’Hare — and thus purely seeing Chicago as a Layover City — before I finally pulled the trigger on leaving the confines of the airport.*

(*Technically I’ve ventured into the city twice due to flight delays; I was a child both times and my only memories were of the hotels and and once getting yelled at for nodding off on a stranger’s shoulder in a taxi. My transportation-based narcolepsy began very early.)

Anyway, I randomly got into baseball this year (that’s a lie, I didn’t, but I kept meeting guys who are super into it) so a sports journalist buddy from Rio 2016 convinced me to fly to Chicago, where he lives and covers baseball, to finally see a game at Wrigley.

I fully expected to drop in, sit through the game, score some talking points with the baseball dudes, and then ghost the city for another 29 years. Eat a hot dog, check it off the list, done.

To everyone’s surprise, I found myself enjoying Chicago so much — the people! The food! The big-city-but-low-drama feel! — that I returned just six weeks later for another weekend. Consider me a Windy City convert.

So after a cumulative 90ish hours in Chicago so far, here are the best things I’ve eaten and drank…for now (because I know I’ve only scratched the surface and will obviously be back):

Chicago Hot Dog

Just like in pizza and comedy, Chicago fights New York for its own claim on a hot dog definition. I’m not enough of an aficionado to really compare, but I’m super into the Chicago version’s requisite soft (like, I aspire to have thread count this soft) poppy-seed bun, and I am here for any dish that demands celery salt and dill pickle spears. The internet also swears not to ask for ketchup, but no Chicago resident I met seemed this upset about the NO KETCHUP rule, so do what feels right in your heart, I guess.

For my Chicago hot dog initiation I went to Portillo’s, which is very much on the beaten track, but there’s pretty much a hot dog shop on every corner and they’re ridiculously cheap, so why not have a few tasters between cocktail bars. Honestly ever since that first one, I now get cravings for those pillowy-soft salty meat tubes all the time. But that could also be the sodium dependency talking.

Brunch, BiXi Beer

When your mood board is: craft beer x Asian fusion comfort food x rooftop patio x brunch, you can bet I’ll be there with my ID (because America) and bells on when the doors open. If Chinese belt noodles, seafood lo mien with lobstah buttah [I cannot say it any other way], lamb wonton, and Sichuan peppercorn dark ale are your jam, then you too should check the newly-opened BiXi out, and also we should maybe be brunch pals.

(Only note: the Vietnamese coffee is well and good but in a conspicuously Americanized way. Like don’t come in with high expectations if you’ve recently spent a significant amount of time housing cà phê đás on the reg in Hanoi.)

Burger, Au Cheval

This was apparently once named the best burger in the nation by Bon Appetit, and thus people will apparently wait hours in line to eat here. Come on a Wednesday lunch service though, and you can waltz your way right into a seat at the counter without knowing either of these things.

But that just speaks to the low-pretension ‘upscale old-school diner’ vibe I got from the place. I don’t know that the burger was “Nothing Is Better In The Entire Country” good, but it — and a side order of hash browns! do it! — are definitely worth the trip to the West Loop (and maybe a mild cardiac health setback).

Cocktails, Scofflaw / The Up Room

In the short time I’ve spent in Chicago I’ve already been taken to nine bars/breweries (hashtag priorities; hashtag do my friends know me or what) and two immediately stood out: Scofflaw, for their gin-heavy cocktail list and ability to nail a perfect Martin Miller’s dirty martini; and The Up Room for an intimate lounge sesh with creative drinks and views like the above. Which are pretty stellar for a cloudy day as is, so you know, extrapolate at will.

Chicago Italian Beef Sandwich

Here we have the full Chicago experience: watching baseball at Wrigley Field, Goose Island beer in one hand, Italian beef sandwich in the other. Even though Wrigley now has this fancy rotating chef pop-up in their concession stands, I obviously had to go for a Chicago steak sandwich on my first visit. I waffled between “hot” or “sweet” (aka giardiniera or roasted green peppers) on top, so I requested half and half and the stand lady gladly obliged. They’re nice like that in the Midwest.

Honorable Mention: Ice Cream, Jeni’s

This was originally higher up the list, but in doing research for this post I learned Jeni’s is a chain(!) from Ohio. Excuse me while I fire my ice cream guy.

However, if you’ve never heard of or been to Jeni’s before, I gotta admit it stands up and is still worth a nibble or seven. Pumpkin 5-spice? Wildberry lavender? GOAT CHEESE ice cream? The flavor creativity is comparable to Salt & Straw from Portland, but with fewer pretentious hipsters, so it’s still a net win for me.

Are you a Chicago fan or not? And where should I hit up next time I’m in town?