Taste Your Way Through Chicago: 20 Must-Try Picks

Chicago is the kind of city where every block smells like something you want to try twice. From sizzling street dogs to white tablecloth legends, there is flavor around every corner waiting for your fork.

You will taste history, neighborhood pride, and a playful spirit that never takes itself too seriously. Bring your appetite and a loose plan, because the best bites often find you first.

1. Deep-Dish Pizza at Lou Malnati’s

That first slice of Lou Malnati’s deep-dish feels like a rite of passage. The buttery, cornmeal-kissed crust cradles rich mozzarella, bright crushed tomatoes, and fennel-spiked sausage that perfumes the air.

You will need patience while it bakes, but the first molten bite makes the wait worth it.

Order a small to share and a chopped salad to cut through the richness. The caramelized edges are the best part, so guard your slice.

Pair with a cold local beer and let the cheese pull become your Chicago souvenir.

2. Italian Beef at Al’s Beef

Get your Italian beef at Al’s and go wet if you are feeling brave. Thin-sliced beef bathes in spiced jus, then gets tucked into a crusty roll that surrenders in the best way.

Add sweet peppers for comfort or fiery giardiniera for that Chicago snap.

It is messy, hot, and deeply satisfying. Stand at the counter, lean forward, and chase drips with napkins like a pro.

You will taste pepper, oregano, and nostalgia in every bite, then wonder why you waited so long.

3. Chicago-Style Hot Dog at Portillo’s

A proper Chicago dog from Portillo’s is a colorful checklist you can eat. Poppy seed bun, snappy Vienna beef, yellow mustard, neon relish, diced onion, tomato, sport peppers, pickle spear, and a whisper of celery salt.

No ketchup, and you will not miss it.

It is crisp, cool, spicy, and warm all at once. Grab crinkle fries for dunking and a chocolate cake shake if you are going big.

This is the city’s handshake in sandwich form, bright, fast, and unforgettable.

4. Alinea’s Tasting Menu

If you want culinary theater, Alinea is the show. Courses arrive as sculptures, aromas, and surprises that make you grin before you taste.

You will lean in, listen, and discover flavors hiding in textures you did not expect.

Reservations demand strategy, but the payoff feels once-in-a-lifetime. Let the team guide the journey and suspend judgment.

You will leave amused, delighted, and a little changed, carrying a new definition of dinner back into the night air.

5. Garrett Popcorn Mix

The Garrett Mix is sweet-salty harmony in a crinkly bag. Caramel Crisp glows like amber, sticking to your fingers, while CheeseCorn dusts everything neon orange.

Together, they become that addictive handful you promise to stop grabbing, then never do.

Grab a warm bag and walk Michigan Avenue with sticky happiness. The aroma trails behind you, drawing questions from strangers.

Pack a tin for later, but know it rarely survives the train ride home.

6. Jibarito in Humboldt Park

The jibarito swaps bread for crispy smashed plantains, and everything suddenly makes sense. Garlicy steak, melted cheese, lettuce, and tomato stack between golden tostones that crunch then give.

Drips of mayo and steak juices are part of the charm.

Humboldt Park does it best, and you will feel neighborhood pride in every bite. Ask for extra garlic sauce if you love bold flavors.

It is messy, soulful, and wildly satisfying without feeling heavy.

7. Harold’s Chicken Shack 1/2 Dark Mild Sauce

Harold’s is a late-night legend for a reason. The half dark arrives hot, crunchy, and drenched in sticky-sweet mild sauce.

White bread soaks the drips while fries hide under the chicken like stowaways.

Shake on lemon pepper and grab extra napkins. The ritual tastes like Chicago after hours, a balance of smoke, sugar, and heat.

You will leave with sauced fingers and a grin you cannot wipe away.

8. Maxwell Street Polish at Jim’s Original

Jim’s Original serves a Maxwell Street Polish that feels like the city’s heartbeat. The sausage snaps, onions char and sweeten, and mustard cuts through the richness.

Sport peppers bring a playful sting that keeps you taking quick bites.

Order at the window and eat standing up like everyone else. It is fast, hot, and deeply comforting.

You will taste history wrapped in butcher paper, humming with traffic and late-night stories.

9. Malört Shot at a Neighborhood Bar

You will hear whispers about Malört, then a dare. This bitter grapefruit-wormwood spirit is not for the timid, but it is a Chicago handshake you earn.

The first sip stings, then lingers with pithy swagger.

Do it at a neighborhood bar and chase with a beer. Laugh, wince, and join the club.

It is not delicious in a traditional sense, yet somehow it becomes a fond story you keep telling.

10. Rainbow Cone on the South Side

The Original Rainbow Cone stacks flavors like a sunny parade. Chocolate, strawberry, Palmer House, pistachio, and orange sherbet arrive in swoops rather than scoops.

Each lick shifts from creamy to citrusy, from nostalgic bakery notes to nutty calm.

It is cheerful and a little messy, exactly right for a warm afternoon. Stand beneath the vintage sign and feel time slow down.

You will leave a little stickier and a lot happier.

11. XO Noodles at Duck Duck Goat

Duck Duck Goat’s XO noodles hit with wok hei and salty heat. Chewy strands catch little bursts of dried seafood umami, chiles, and scallions.

You will slurp quickly, then slow down to chase every glossy strand.

Pair with soup dumplings and a bright cocktail. The room buzzes, and the plates feel like a playful tour through flavors you already crave.

It is comfort with swagger, designed for sharing but hard to surrender.

12. Cheeseburger at Au Cheval

The Au Cheval burger is glossy, gooey perfection. Thin patties with lacy edges, American cheese melting into every crevice, and dijonnaise tying it together.

Add thick-cut bacon or a fried egg if you want extra decadence.

Expect a wait, but the bar is friendly and the payoff huge. The first bite drips down your wrist in the most endearing way.

You will dream about that salty, beefy balance for weeks.

13. Birria Tacos in Pilsen

Pilsen’s birria scene turns a craving into a mission. Tortillas crisp in chile-stained fat, hugging tender beef and melted cheese.

Dunk each taco into steamy consommé, then hit it with lime and cilantro for balance.

Stand at a curb, napkins ready, and chase each bite with a sip of broth. You will feel heat, richness, and joy in quick succession.

It is the kind of street food that makes time stop.

14. Saganaki at Greek Islands

At Greek Islands, saganaki arrives sizzling and ready for drama. A quick splash and a fiery Opa send flames leaping, then a lemon squeeze tames the heat.

The cheese stretches, salty and plush, begging for warm bread.

It is theatrical without feeling fussy, perfect for sharing with friends. Order grilled octopus and a carafe of wine to round it out.

You will leave glowing, smelling faintly of lemon and flame.

15. Smoked Fish at Calumet Fisheries

Calumet Fisheries feels like a delicious field trip. The smokehouse perfumes the air, and the fish emerges lacquered, tender, and quietly perfect.

Smoked shrimp snap sweetly while salmon flakes with a deep, campfire whisper.

Grab a paper tray and eat outside by the bridge. It is simple food that tastes like patience and craft.

You will drive back into the city with a satisfied silence and a salty grin.

16. Pie at Bang Bang Pie & Biscuits

Bang Bang makes pie that tastes like Sunday afternoon. Flaky crust shatters gently, then gives way to bright, custardy comfort.

Seasonal flavors rotate, but key lime and chocolate chess never disappoint.

Pair a slice with strong coffee and a biscuit if you are truly treating yourself. The room feels cozy, like a friend’s kitchen with better butter.

You will leave plotting your next flavor before the plate is clean.

17. Frontera Grill’s Mole

Frontera’s mole hugs the plate like velvet. Chocolate, chiles, nuts, and spice weave into a sauce that keeps revealing new notes.

Tender chicken and warm tortillas make the perfect partners for scooping.

Sip a margarita bright with lime and sea salt. It is celebratory yet rooted, the kind of dish that teaches patience and craft.

You will catch yourself slowing down to savor every last smear.

18. Oblong Pub Pizza at Pequod’s

Pequod’s turns pan pizza into a caramelized obsession. Cheese climbs the edges and crisps into a lacy, dark crown that crackles under your bite.

The sauce tastes bright and peppery, balancing the buttery heft.

It is shareable, but you will fight for the corner pieces. Order a pitcher and settle in for a slow, satisfying meal.

You will think you are full, then keep reaching for one more square.

19. Doughnuts at Do-Rite Donuts

Do-Rite makes mornings feel special. The old fashioned is craggy and tender, soaking up glaze like a dream, while maple bacon walks the sweet-savory tightrope perfectly.

Seasonal flavors keep things fun without going overboard.

Grab a few and a strong coffee, then find a bench outside. It is simple happiness, handheld and still warm.

You will plan your return before the sugar dust settles on your lap.