The 15 Most Essential Food Experiences in Chicago
These dining experiences should be at the top of your culinary bucket list.
As a dining city, there’s something truly singular about Chicago. A massive metropolis, it’s the rare urban hub that feels at once glitzy and global while retaining an air of modesty and a lack of pretense. It’s a sentiment felt through every facet of local culture, but perhaps nowhere is this more evident than on the plate. One of the few Michelin-ranked cities in the country, and the new home for the James Beard Foundation Awards, Chicago certainly has the chops to call itself among the best dining cities, but between all the tasting menus and highfalutin cocktails and splashy openings, the city is just as passionate about its neighborhood taquerias and hot dog stands.
In the Second City, requisite dining experiences run the gamut—from frills-free carnitas to multi-course degustations from A-list chefs. A place like this, as brassy and bold and multifaceted as a city can get, can be hard to narrow down into a hit list of essential eats. After all, one could live here for a decade and barely scratch the surface, especially considering the endless rapid-fire spate of new openings. But if you’re looking to get a true taste of Chicago, from the fancy to the unfussy, and from cinnamon rolls to $100 cocktails, consider these the premiere food and drink experiences you absolutely can’t miss if you really want to sink your teeth into this Second to None City.
The Bear Chocolate Cake at Loaf Lounge
Chicago isn’t lacking for movies and television shows set in its midst, but rarely does a show capture the authentic atmosphere and ecosystem of the city quite like The Bear. The series, which featured the brutally honest trials and tribulations of life working at an Italian beef restaurant, captured the obsessive gaze of Chicagoans and out-of-towners alike, and aside from a mild obsession with the show’s lead actor, the real star of the show was the chocolate cake. A feat of fudgy goodness, this multi-layered beaut is the handiwork of Sarah Mispagel, a seasoned pastry chef who served as a consultant for The Bear, and whose confections stole the show. Along with her husband Benjamin Lustbader, she owns Avondale’s recently opened Loaf Lounge, where the same cake from the show is on the menu. Made with Valrhona, from the cake itself to the glistening ganache, and studded with thick and fluffy layers of chocolate frosting, it’s got the look of pure Americana in all its decadent glory. Portillo’s chocolate cake shake, eat your heart out.
Breakfast Sandwich at Kasama
You might think that there's only so much one can do with a seemingly simple egg sandwich, but Kasama has proved that within simplicity lurks great creativity and yes, even divinity. The egg, a perfectly textured lightly souffled square. The sausage, an exquisitely meaty caramelized homemade longganisa patty. The cheese, a gooey slice of American. And, finally, the bread, a sliced-open airy potato roll. And if you know what's good for you, add a hash brown to the stack, perfectly crunchy on the outside and soft on the inside. The result is guaranteed to brighten up even the dreariest Chi-town winter morning.
Tiki Cocktails from Three Dots And A Dash
This subterranean tropical temple has been tunneling into our hearts since 2013. And a decade later, Three Dots has established itself as one of the premiere cocktail lounges in all of Chicago—and beyond. The recipe is escapism. It could be the dead of winter but it’s perennially paradise inside, with a vibe that feels more Pirates of the Caribbean than polar vortex. Under the tipsy tutelage of beverage director Kevin Beary, the menu reads like a tropical travel itinerary filled with Polynesian classics and boozy novelties, all served up in dazzling, whimsical vessels that range from barrels and skulls to an octopus. Rum is king, and while you really can’t go wrong with any of the tipples, some standout staples include the namesake Three Dots and a Dash (a blend of aged Martinique rhum agricole, aged guyana rum, lime, orange, falernum, and allspice), the Future Mai Tai (single barrel aged Martinique rhum agricole, Japanese whisky, Yellow Chartreuse, lime, and five spice orgeat), and the hilarious Shotstapus, a collection of rum-based shots served on elaborate octopus arms.
Is it actually pizza? Or is it a tomato and cheese casserole? Yes. Labels be damned, we can all agree that this unapologetically thicc, Chicago-born legend is also unabashedly delicious. And both locals and newcomers delight in the fact that no two pies are the same, from lauded chains like Giordano’s, Pizzeria Uno, Lou Malnati’s, and Gino’s East to smaller neighborhood operations like The Art of Pizza, and Bartoli's, try to catch ‘em all. Though if you have time to taste just one, make it Pequod’s in Lincoln Park. The crisped, caramelized edges of their crusts are without parallel.
Drinks and a show at the Green Mill
Make like modern day Scarface at this landmark cash-only jazz bar, known for incredible live music, stiff cocktails, and a deeply seedy history as Al Capone’s Prohibition-era headquarters. Rumor has it a network of tunnels still lies beneath the floorboards, connecting the watering hole to different former gangster hangouts all over the Northside. It’s touristy, sure, but the spooky-swanky atmosphere—not to mention the world-class nightly performances—is well worth waiting out the crowds.
Chicago-style hot dogs
Leave it to a city built on meat-packing to produce the world’s perfect hot dog: An all-beef frankfurter plopped into a steamed poppy seed bun and “dragged through the garden,” as they say, collecting a hoard of yellow mustard, neon-green relish, chopped white onions, tomato wedges, spicy sport peppers, a dill pickle spear, and a shake of celery salt in its wake. Just as important as what’s on it is what’s not on it: ketchup. Get yours at a plethora of Chicagoland stands, quick-serve outposts, and even sit-down restaurants, each spot more colorful and charming than the last. Standouts include Fatso’s Last Stand, Superdawg Drive-in, Wolfy’s, Gene & Jude’s, Dog Haus Biergarten, Lulu’s, Jimmy’s Red Hots, The Duck Inn, Scatchell’s Beef, Portillo’s, Byron’s, and the Wiener Circle, where the staff famously serves their char dogs with a side of expletive-streaked sass.
Smoked Shrimp at Calumet Fisheries
This humble Far South Side fish shack has been marinating and smoking their prime seafood over specially selected oak logs onsite since 1948 and, unlike pretty much everything else in this crazy precious world, little about their award-winning process has changed. The menu runs deep, of course, but the shrimp, tender and bursting with briny succulence, remains an absolute no-brainer.
Chorizo-stuffed bacon-wrapped dates at Avec
West Loop and River North
When this West Loop pioneer opened back in 2003, the elegant yet approachable eatery quickly made a name for itself thanks to sleek communal tables, a forward-thinking wine list, and, most importantly, the juiciest medjool date dish the Midwest had ever encountered. Plump dates undergo the full hog treatment here, plied with spiced chorizo sausage before being wrapped in a thick slab of bacon, fired until crisp and crackling, and doused in a warm piquillo pepper tomato sauce that practically demands a hunk of good, freshly baked bread. Don’t think, just order.
Off-menu Beijing duck dinner at Sun Wah BBQ
Gather up your poultry posse and prepare to sink your collective teeth into this Uptown fixture’s not-so-secret signature dish: a gut busting, multicourse bonanza showcasing an entire duck, freshly roasted and sporting a layer of ultra succulent, crispy skin, carved tableside for your mouthwatering pleasure by the family-run spot’s expert staff. If you don’t know, now you know.
Rare Spirit Cocktails at Milk Room
A far cry from speakeasies of yore, when discreet drinkers would swig cheap booze down dingy alleyways, Milk Room takes the whole clandestine concept and evolves it into a mecca of decadent mixology. And by “decadent,” we mean the spirits are so coveted and rare that some cocktails go for $100 a pop. The intimate watering hole, self-described as a “micro bar,” is an eight-seat nook nestled in the Chicago Athletic Association hotel, is a true must-visit for cocktail connoisseurs—especially those who value hooch with a side of history, shaken and stirred with dexterous artistry by sharply dressed barkeeps.
Single cheeseburger at Au Cheval
Fad foods come and go, but this West Loop haunt’s multi-award-winning cheeseburger—a scrumptiously sloppy pile of prime W.W. Johnson Farms beef griddled to greasy perfection, goopy American cheese, housemade pickles, a runny fried egg, thick-cut bacon, and a dollop of tangy Dijonnaise spread stuffed into a buttery double-toasted bun—is undoubtedly forever. Pair it with a frosty $3 tallboy and a Dr. Devon’s Pickleback shot for the full experience. If you’re joined by dining partners, be sure to split the restaurant’s signature fried bologna sandwich to serve as a gut-busting appetizer like no other.
W.R.’s Chicago Cut at Gibsons Bar & Steakhouse
Steakhouses are to Chicago what pubs are to London—they’re entrenched in the city’s dining DNA. From old-school joints populated by schmoozing politicians to newfangled glitz at see-and-be-seen hot spots, the city’s steakhouse scene is also as deep and diverse as it is meaty. For a taste of true-blue Chicago, opt for the signature W.R.’s Chicago Cut—so named for former Chicago Tribune food critic William Rice—at Gibsons Bar & Steakhouse. An icon in the Gold Coast, and routinely the highest-grossing independent restaurant in town, the steakhouse was the first in the country to get its own USDA certification program, ensuring the utmost in Prime beef. The 22-ounce W.R.’s Chicago Cut, a richly marbled bone-in rib-eye, is the cream of that crop, especially when paired with a double-baked potato and Brussels sprouts with maple-bourbon butter.
Butter Chicken Calzone at Superkhana International
The word “fusion” gets thrown around with reckless abandon, but if there’s one restaurant in town threading the needle effectively, it’s Superkhana International. The vibrant Logan Square beacon, a partnership between chefs Yoshi Yamada and Zeeshan Shah and Lula Cafe’s acclaimed Jason Hammel, is a restaurant that specializes in contemporary Indian cuisine, to put it mildly. We’re talking paneer-flecked pizzas, green chile naan, and masala-spiced bolognese. But the crowning achievement is the butter chicken calzone, an almost audaciously over-the-top dish that enrobes buttery, gravy-rich chicken thighs in a naan-like crust, alongside mozzarella and Amul cheeses for added molten effect. It’s all brushed with ghee before baking in a scorching oven and emerging as the comfort food of your fusion fantasies.
Lobster Dumplings at S.K.Y.
This New American hotspot headed by chef Stephen Gillanders is forging the way when it comes to borrowing and blending flavors from all across the globe in the most effortless manner. The menu pulls especially from Asian cuisine, a nod to Gillander’s roots cooking in the kitchen with his grandmother, but everything on the menu is outstanding, from the Fried Chicken with a side of creamed corn and homemade hot sauce to the Foie Gras and Mushroom Bibimbap. But before skipping right to entrees, prime your palate with an order of the Lobster Dumplings—thin dough filled with soft lobster meat and served doused in an infectiously buttery herbed sauce.
Hot Fudge Banana Split at Margie’s Candies
Slide into one of Margie’s Candies worn leather booths and revel at the vintage decor harkening back to its debut in 1921. This century-old confectionery is known for its assortment of housemade candies, but the real show-stoppers are the ice cream concoctions, and the Hot Fudge Banana sundae, served inside an old timey tulip bowl, is the granddaddy of them all. The masterpiece spans three massive scoops of ice cream, bananas, fresh whipped cream, bright red cherries, and crisp cookies, drenched in homemade caramel and fudge, and sprinkled with chopped nuts. The cool ice cream, the warm fudge, and the crunch of the cookie is such a glorious combination that you may find yourself engaged in a spoon war with your dining companion.
Elanor Bock is a contributor for Thrillist.
Matt Kirouac is a travel writer with a passion for national parks, Disney, and food. He's the co-founder and co-host of Hello Ranger, a national parks community blog, podcast, and app. Follow him on Instagram.