There’s a moment every Chicagoan knows well: your out-of-town friends show up and expect you to be their personal tour guide, especially when it comes to food. And somehow—somehow—you find yourself standing in line for yet another deep dish pizza.
Don’t get me wrong. Deep dish has its place. But if I could rewind time, I’d have steered my guests off the cheese cliff and into the world of Chicago’s unexpectedly awesome Asian fusion, smoky meats, jibaritos, and late-night jazz ravioli. Here’s the food tour I wish I gave them—aka, my redemption itinerary.
Day 1 – Casual Arrival, Big Flavors
🥩 Green Street Smoked Meats
No need for reservations, which is perfect because, of course, they’re late. This is the ultimate walkable, come-as-you-are welcome meal. And let’s talk about that pastrami—it’s game changing. You don’t just eat it. You sit down and have a moment with it.
Backup plan: If the food gods smile, maybe we slide into High Five Ramen. If not, I’ll take ’em to Momotaro Izakaya, where the burger is pure umami heaven.
🍸 Moneygun
No food tour is complete without a proper nightcap. Classic cocktails done right. Stylish but not stuffy. A vibe you can’t get in Cleveland (no shade).
Day 2 – Layered Like a City Dog
☕️ Standing Passengers (or Home Coffee)
I’m not a breakfast guy, so we’ll keep it light. But if we sleep in, Standing Passengers’ meatball sub will wreck your life in the best way.
🌭 Chicago Dog by the Aquarium
Forget tourist traps. Grab a classic dog at the stand in front of the Shedd Aquarium, stroll the lake, maybe pop into a museum. Hotdog in one hand, skyline in the background. That’s the real Chicago experience.
🍹 Three Dots and a Dash
It’s tiki hour, baby. Wild cocktails in an underground lair. If we’re starving, we’ll get the pu pu platter, because even the name is fun to say after two rum punches.
🍝 Dinner at Andy’s Jazz Club
Where else can you eat incredible ravioli while a live jazz trio serenades your meal? It’s my secret move. Cozy, vibey, and a killer sendoff to the day.
Day 3 – Dim Sum and a Fond Farewell
🥟 MingHin or Phoenix (Chinatown)
The morning starts slow with dim sum in Chinatown, the underrated jewel of Chicago’s food scene. Lazy Susans spinning. Dumplings dropping. You’re not a guest anymore—you’re a convert.
If they still haven’t tried a jibarito, I’m tossing them in a Lyft to Café Central. Plantains > bread. Fight me.
Alternate Realities: If My Guests Were From the West Coast…
Had they rolled in from LA or SF, I’d have upped my game. Think: Indian food on Devon, or a splurge at a chef-driven spot like Jeong, Kai Zan, or Indienne. If they were feeling fancy, maybe even Oriole or whispers Alinea. But I’m not dropping Alinea on people still recovering from Cleveland hot takes.
Final Thoughts
Chicago’s food scene is more than its stereotypes. Don’t let deep dish be the whole story. Next time, I’m planning the food tour I wish I gave—bold, diverse, deliciously sneaky. And my guests? They’re gonna leave raving about pastrami, jazz ravioli, and jibaritos.
