I’ve been eating my way through Chicago for nearly three decades, and somehow, the thrill never fades. Maybe it’s the city’s unique balance—a cosmopolitan food scene that still feels grounded, approachable, and wonderfully unpretentious. Here, you can walk into a neighborhood joint in your oldest jeans, order a plate of something extraordinary, and feel like you belong.
This is a city where global flavors live side by side with old-school classics. Where you can score a flaky Lithuanian bacon bun, spoon into Senegalese thieboudienne, or sink your teeth into a Serbian walnut cookie—sometimes all on the same block. Sure, we’ve got buzzy neighborhoods like the West Loop and Wicker Park, where Michelin stars sparkle. But my essential Chicago food tour leans toward soul-soothing comfort and character—dishes that carry stories, culture, and flavor in every bite.
Let’s dig into a few of the places that make this town taste like home.
Crisp: A Korean Spin on Comfort Food
Step into Crisp, and you’ll quickly realize this cheerful spot takes its chicken seriously. Piles of jumbo wings and drumsticks are standard issue here, crispy and golden beneath a glossy coat of soy-ginger Seoul Sassy sauce. The crackly skin gives way to tender, flavorful meat—and suddenly you understand why everyone in the room looks like they’re having a spiritual experience with poultry.
But it’s not just about the bird. Crisp’s Buddha Bowls—modern riffs on Korean bibimbap—are just as crave-worthy. My go-to is the Bad Boy Buddha: a vibrant mountain of marinated veggies over rice, crowned with a runny fried egg. Sweet, spicy, crunchy, soft—it’s a whole mood in a bowl.
2940 N Broadway | 773-697-7610
Dat Donut: Where Bigger Really Is Better
Long before gourmet doughnuts became Instagram darlings, Dat Donut was serving sweet, glazed glory on Chicago’s South Side. The crown jewel? The Big Dat. This palm-sized colossus clocks in at seven inches wide, yet it’s anything but heavy. The glaze shatters gently, revealing a light, spongy interior that defies its hulking size.
If you’re more into fillings, try the custard doughnut—a powdered-sugar-coated beauty with rich, eggy cream inside. Everything’s made fresh, 24 hours a day, six days a week. Watch the bakers roll and fry dough behind the glass, and you’ll understand why this spot has stayed beloved for decades.
8251 S Cottage Grove Ave | 773-723-1002
Margie’s Candies: Sundaes Straight Outta Time
Margie’s is pure vintage charm—jukeboxes, knickknacks, red booths, and sundaes that could bring Sinatra back to life. Since 1921, this ice cream parlor has served up nostalgia by the scoop, including to such patrons as Al Capone and The Beatles.
The sundae arrives grandly: scoops of butterfat-rich housemade ice cream in a clamshell bowl, a mountain of whipped cream, and a silver gravy boat of hot fudge on the side. That fudge—thick, dark, and just the right amount of sweet—is the stuff of legend. You might not finish the whole thing, but you’ll die trying.
1960 N Western Ave | 773-384-1035
Dove’s Luncheonette: Diner Meets Desert Heat
Dove’s is what happens when a retro diner marries Tex-Mex soul. Park yourself at the counter, sip coffee to a Curtis Mayfield soundtrack, and let the scent of chorizo gravy float over your shoulder.
This isn’t your average greasy spoon. Dishes like chicken-fried chicken smothered in spicy gravy or crispy potato hash with shishito peppers elevate comfort food to high art. And don’t sleep on breakfast—especially the granola-dusted flapjacks served in a skillet with bittersweet chocolate sauce. Bonus: tequila flows from sunrise to sundown, just as Dove Linkhorn (the hustler from Algren’s A Walk on the Wild Side, for whom the place is named) would have wanted.
1545 N Damen Ave | 773-645-4060
Giordano’s: Stuffed Pizza That Pulls No Punches
Think deep-dish is heavy? Wait ‘til you meet its bigger, bolder cousin: stuffed pizza. Giordano’s does it best, layering cheese between two crusts, then ladling tangy tomato sauce over the top. Each slice is a commitment—over half a pound, with crust that rises like a carb monument.
The Rush Street location is a people-watching paradise. Watch tourists’ eyes widen as the molten cheese stretches like a mozzarella waterfall. Some grab forks; others go full barbarian. Either way, it’s beautiful.
730 N Rush St | 312-951-0747
Hopleaf: Beer, Belgians, and the Best Sandwich in Town
Andersonville’s Hopleaf is a temple for beer lovers. With 68 taps and a bottle list that reads like a novel, it’s easy to get overwhelmed—but the food will keep you grounded.
Sure, the ale-steamed mussels are famous. But the CB&J—a gooey combo of cashew butter, fig jam, and raclette cheese grilled on sourdough—is the unsung hero. Add a side of peppery Stilton mac, and you’ve basically found nirvana. Warning: you will need napkins.
5148 N Clark St | 773-334-9851
The Green Mill: Jazz, Gin, and Gangster Lore
Capone’s favorite haunt still oozes speakeasy swagger. At the Green Mill, velvet booths curve under golden light, and martinis come stiff and classic—just gin, two olives, and a whiff of danger.
Live jazz rules the night, and poetry slams take over Sundays. If you’re lucky, someone might show you the trapdoor behind the bar that once led to bootlegger tunnels. And yes, you can sit in Capone’s booth—he liked to keep both doors in sight.
4802 N Broadway | 773-878-5552
Cafe Central: Where the Jibarito Was Born
Forget ciabatta—Chicago gave us the jibarito. Created in the ’90s by local legend Juan “Pete” Figueroa, this sandwich swaps bread for crisp-fried plantains and fills it with steak, cheese, lettuce, tomato, and garlicky mayo.
At Cafe Central, you get the real deal. No sky-high stacks or greasy rivers here—just a tidy, tender, totally devourable sandwich in a cozy mom-and-pop spot that’s been serving Puerto Rican comfort food since 1952.
1437 W Chicago Ave | 312-243-6776
Lou Mitchell’s: Breakfast with a Side of Americana
Open since 1923, Lou Mitchell’s is part Greek diner, part Route 66 museum, and 100% heart. From the waitresses who call you “sweetie” to the free donut holes while you wait in line, this place is old-school in all the right ways.
Order the feta omelette, thick-cut Greek toast, and a side of stewed prunes (trust me). By the time you’ve polished off your soft-serve dessert and gotten a box of Milk Duds on your way out, you’ll believe again in breakfast—and humanity.
565 W Jackson Blvd | 312-939-3111
Di’s Den: Where Chicago Keeps It Real
No fancy cocktails. No kale chips. Just a barstool, a beer, and a few die-hard Cubs fans yelling at the TV. Di’s Den is a true neighborhood spot on the Northwest Side where construction workers and nurses unwind with a High Life and a side of unfiltered commentary.
The dartboard sees more action than the jukebox—unless there’s a game on. Win or lose, Di herself might pour you an apple pie shot. Places like this are what keep Chicago honest.
5100 W Irving Park Rd | 773-736-7170
