There’s a moment every Chicagoan knows well: your out-of-town friends show up and suddenly expect you to become a culinary tour guide. And without fail, you end up waiting in line for another deep dish pizza.

Don’t get me wrong—deep dish has its moment. But if I could hit rewind, I’d skip the cheese cliffs and take them on a true culinary adventure through smoky meats, Asian fusion, jibaritos, dim sum, and jazz-accompanied ravioli. So here it is: the food tour I wish I gave them. A redemption itinerary. A guide for anyone who wants to explore a tastier, more vibrant Chicago.

Day 1: Casual Arrival, Big Flavors

🥩 Green Street Smoked Meats

No reservations, no fuss. Green Street Smoked Meats is the ultimate welcome meal. Think: Texas-style brisket, pastrami so rich it demands silence, and twinkly lights hanging above long picnic tables in a loading-dock-chic setting. This is comfort food done right with zero pretense.

Local Tip: Order the pastrami and thank me later. Oh, and don’t sleep on the Frito pie.

🍻 Backup Plan: High Five Ramen or Momotaro Izakaya

If your crew is into ramen and willing to wait, High Five Ramen hits with intense, creamy broths and basement speakeasy vibes. No room? Head upstairs to Momotaro Izakaya for an umami bomb of a burger and top-tier skewers.

🍸 Moneygun

After dinner, head to Moneygun for classic cocktails done with flair. It’s dimly lit, vibey, and unpretentious. Whether you’re in the mood for an old fashioned or a spicy paloma, they’ll make it better than anywhere else.

Day 2: Layered Like a City Dog

☕️ Standing Passengers or Home Coffee

Not everyone wakes up early, especially after tiki drinks. Standing Passengers serves up good vibes and coffee in an art-gallery-meets-espresso-bar space. Late risers? Their meatball sub might change your life.

🌭 Chicago Dog Outside the Shedd Aquarium

Forget the classic hot dog chains. The tiny stand in front of the Shedd Aquarium serves up no-frills, absolutely perfect Chicago dogs. Grab one, stroll the Lakefront Trail, and soak up skyline views.

Bonus: Pop into the Field Museum or Shedd if you’re feeling touristy. But honestly? A hot dog and skyline might be the best Chicago moment you can gift someone.

🍹 Three Dots and a Dash

Hidden down an alley and behind a nondescript door lies one of the best tiki bars in the country. Three Dots and a Dash is part escapist fantasy, part masterclass in mixology. The drinks are strong, the mugs are whimsical, and if you spring for the pu pu platter, you’ll eat well too.

🍝 Dinner at Andy’s Jazz Club

Yes, you can eat pasta while a jazz trio plays live five feet away. Andy’s Jazz Club serves up top-notch ravioli, steak frites, and risotto alongside nightly jazz sets. It’s classy without being uptight and intimate without being awkward.

Insider Move: Reserve a table for the early show (6 p.m.) for more room and a quieter crowd.

Day 3: Dim Sum and a Fond Farewell

🍟 MingHin or Phoenix in Chinatown

Start slow with dim sum in Chinatown—a criminally underrated corner of Chicago. MingHin is sleek and modern with a wide variety of dishes (pro tip: get the baked BBQ pork buns), while Phoenix is the old-school rolling cart experience.

Toddler-friendly Tip: Many Chinatown spots open early, and the round tables with spinning Lazy Susans make for fun group dining with kids.

🥪 Jibarito at Café Central

If your guests haven’t tried a jibarito—Chicago’s Puerto Rican masterpiece where fried plantains replace bread in a steak sandwich—take them to Café Central. It’s hearty, messy, and unforgettable.

Not into meat? Ask for a veggie or chicken version. It still slaps.

Optional Upgrades (For the West Coasters)

Hosting foodies from LA, SF, or NYC? Pull out the big guns:

• Jeong: Korean-American tasting menu magic.
• Kai Zan: Intimate omakase-style sushi.
• Indienne: Elevated Indian dining with beautiful plating.
• Oriole or Alinea: Michelin-starred experiences for when you want to show off (and have time to book months in advance).

What We Learned

• Don’t overschedule. One or two food-focused stops per day is plenty.
• Let the city do the work. Walking between bites gives you views, energy, and time to digest.
• Always have a Plan B. Long wait? Closed kitchen? Have a backup. In Chicago, it’s easy.

This isn’t just a Chicago food tour—it’s a love letter to the city’s hidden flavors and underappreciated gems. From smoky meats and underground tiki bars to Chinatown mornings and jazz-filled pasta nights, Chicago is bursting with delicious surprises for those willing to look beyond the deep dish.

So next time your friends come calling, don’t default to cheesy tradition. Show them the real Chicago—a city layered with culture, comfort, and culinary creativity. And maybe, just maybe, they’ll leave dreaming of jibaritos and jazz ravioli instead of pepperoni and sauce.