All-Time Greats

The 25 Most Essential Chicago Food Experiences

Get started on them ASAP.

If the tumultuous modern world has taught us anything it’s that life is as precious as it is unpredictable. Why not make the most of your time on this wild and wonderful planet by eating and drinking your way through some of its most appetizing cities? Get your appetite good and whetted by sampling these 25 must-tries from our kind of town, Chicago. 

Pequod’s  pizza

Deep-dish pizza

Multiple locations
Is it actually pizza? Or is it tomato and cheese casserole? Regional squabbles aside, we can all agree that this unabashedly thick Chicago-born legend is damn 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’s, Lou Malnati’s, and Geno’s East to smaller neighborhood operations like The Art of Pizza, Bartoli's, and Lincoln Park’s beloved Pequod’s (this writer’s personal pick, for what it’s worth). Try to catch ‘em all. 
How to order: Contact your preferred shop directly for reservations, pick-up, or delivery or order online via GrubHub, Caviar, Uber Eats, DoorDash, and Postmates.

Rib tips
Rib tips sandwich | Photo by Jim Vondruska

Rib tips 

Multiple locations
North Carolina bleeds pulled pork, Kansas City knows burnt ends, and Texas has brisket on lock, but when it comes to Chicago BBQ, it’s all about rib tips. Tried-and-true smokeshacks like Lem’s, Leon’s, Fat Willy's Rib Shack, Uncle John’s, Earl’s, Robinson's No. 1 Ribs, and Trice’s Original Slab usually cook up these chewy, saucy originals slow and low in massive aquarium smokers before dishing them out to hungry meat fiends the city over. Get in line, pronto—you’re going to want seconds.
How to order: Contact your preferred shop directly for onsite dining, pick-up, and delivery or order online via GrubHub, Uber Eats, and DoorDash.

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.
How to order: A brand new pandemic-fueled tented outdoor area keeps customers distanced and happy with drink service, concerts, and dancing most nights. The bar also streams select performances live online so you can stir yourself up a martini and enjoy the show from home. Keep an eye on the calendar for more info.

Chicago-style hot dogs

Multiple locations
Leave it to a city steeped in 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 relish, chopped white onions, tomato wedges, spicy sport peppers, a dill pickle spear, and a shake of celery salt in its wake. 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, The Duck Inn, Satchell’s Beef, Portillo’s, Bangers & Lace, Byron’s, hipster favorite Hot G Dog, and the Wiener Circle, where the staff famously serves their char dogs with a side of expletive-streaked sass.
How to order: Contact your preferred sausage slinger directly for onsite dining, pick-up, and delivery or order online via GrubHub, Uber Eats, Caviar, Postmates, and DoorDash.

Cinnamon roll at Ann Sather

Pairs of satisfyingly chewy, oven-fresh, made-from-scratch cinnamon buns, intensely aromatic and drenched in a thick, creamy glaze, are the name of the game inside this long-revered breakfast hotspot. One whiff and you’ll never fall victim to a greasy mall kiosk bun-slinger again, we guarantee it.
How to order: Contact your preferred location directly for onsite dining, pick-up, and delivery or order online via DoorDash, GrubHub, Postmates, and Uber Eats.

Flaming saganaki at Santorini

Who among us would refuse a block of fried white cheese glistening with oil and sizzling under the scorching blaze of an open flame? Another sneaky Chicago invention, Greektown stalwart Santorini’s flaming saganaki effortlessly evokes the exact kind of tableside whimsy we could all use right now. Not yet up to dining onsite? Feel free to try this one at home—just make sure to watch your eyebrows.
How to order: Stop by Santorini's website for information on onsite dining reservations and carry-out or order online via Uber Eats, Postmates, and GrubHub.

Smoked shrimp at Calumet Fisheries

South Deering
This humble Far South Side fish shack has been marinating and smoking their prime seafood over specially selected oak logs onsite since in 1948 and, unlike pretty much everything else in this crazy world, precious little about their award-winning process has changed. The menu runs deep, of course, but the shrimp, tender and bursting with briny, meaty succulence, remains an absolute no-brainer.
How to order: Stop into the one and only E. 95th Street smokehouse for take-out or call your order into 773-933-9855

The Garrett Mix from Garrett Popcorn

Multiple locations
No Midwestern holiday photograph is complete without a family-sized tin of Garrett’s popcorn lurking in the background. The most popular option, a salty-sweet duo of Cheddar cheese and toffee-sticky caramel corn, tastes like a mix between Christmas morning bliss and childhood cavities. Ah, memories.
How to order: Pick up in person at one of Garrett’s six storefront and kiosk locations, order delivery from Postmates, or have it shipped from straight from the source.

Fried chicken with mild sauce from Harold’s Chicken Shack

Multiple locations
It might make up the bulk of the meal, but this storied regional chain’s beautifully scalded fried chicken takes a backseat to its prized mild sauce, a tomato-tinged, tartly sweet, smoky, and ever-so-slightly spicy potion that lurks quietly in the back of every Chicagoan’s childhood food memories. We’ll take ours with a side of wings and fries, please and thank you.
How to order: Head any one of the chain’s Chicagoland locations for onsite dining and carry-out or order delivery online via DoorDash, GrubHub, Postmates, and Uber Eats.

Chorizo-stuffed bacon-wrapped dates at Avec

West Loop
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.
How to order: Head to Tock for onsite dining reservations and pick-up options or order delivery online via DoorDash and Postmates.

Italian beef 

Multiple locations
Any good Chicagoan knows our fair city is known far and wide for three specific belt-busting dishes: Chicago-style hot dogs, deep dish pizza, and, perhaps most significantly, Italian beef sandwiches. Why? Step inside one of the area’s many choice beef dealers, from familiar chains like Jay's Beef, Portillo's, Pop's, Al’s, and Buona to mom and pop operations like the Original Chickies, the Original Mr. Beef, Roma's, Johnnie's, Luke's, Freddy's, Scatchell's, and South Side giant Tony's, and you’ll soon find out. That pile of broth-soaked shaved roast beef, dumped onto puffy Italian bread and smothered in sweet marinated peppers or spicy giardiniera, is well worth the inevitable belly ache.
How to order: Contact your preferred location directly for onsite dining, pick-up, and delivery or order online via DoorDash, GrubHub, Postmates, and Uber Eats.

Off-menu Beijing duck dinner at Sun Wah

Gather up your pandemic pod 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.
How to order: Call 773-769-1254 to secure onsite dining reservations or place an order for curbside pick-up.

Tamales from the Tamale Guy

Ukrainian Village
In the before times, local bar-goers would let out a cheer each time Claudio Velez, better known as the fabled Tamale Guy, ambled through the door toting his iconic red cooler packed full of hand-rolled tamales. And now that casual indoor bar hangs might be a thing of the past (sniff, sniff), Claudio and the team have thankfully set up shop inside the former Whisk space on Chicago Avenue so the tamale faithful can continue to get their expertly seasoned, endlessly tender chicken, pork, or cheese and pepper fix by the dozen, this time during daylight hours.
How to order: Stop into the new Chicago Ave storefront for onsite dining and instore pick-up or check out the website for delivery and take-out.

Rainbow cone at the Original Rainbow Cone

Ah, the rainbow cone. Visually radiant and teeming with fruity, sugary goodness, it’s what every ice cream cone wants to be when it grows up. And no long, hot, unbearably sticky Chicago summer would be complete without at least once attempting to devour this handheld mountain of chocolate, strawberry, Palmer House (aka vanilla with cherries and walnuts), pistachio, and orange sherbet in full before it topples over and melts into technicolor sidewalk sludge. Godspeed.
How to order: Grab a cone in-person at either location, track the ice cream truck schedule for pop-up appearances, or get it delivered via GrubHub, Postmates, and Uber Eats.

Single cheeseburger at Au Cheval

West Loop
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.
How to order: Stop into the Randolph Street diner for onsite dining, nab carry-out on Toast, or head to Caviar and DoorDash for all your delivery needs.

The Chicago Handshake (aka a Malört boilermaker)

Multiple locations
Malört, the gasoline-scented wormwood liqueur Chicagoans love to hate, is not so much an area tradition as it is a rite of passage. Or maybe a dare? Either way, no self-respecting boozehound can leave the Windy City without downing a shot or two of the amber-hued elixir. And those in the know opt for the Chicago Handshake, a dive bar classic that tempers the evil spirit with a chilly can of macro lager like Hamm’s or Old Style. 
How to order: Belly up to the bar in person (safely and politely, of course) or take the party home with delivery or take-out from Maria’s Packaged Goods, Haymarket Pub & Brewery, Revolution Brewing, Nisei Lounge, and CH Distillery.

Jibarito at Jibaritos y Más

Logan Square, Lincoln Park
A Puerto Rican original born on the mean streets of Chicago, this Logan Square cult favorite’s flagship sandwich is a work of culinary genius. Replacing boring old bread with crunchy, juicy slabs of fried smashed plantains? Check. Cramming the whole thing full of richly seasoned roast pork, cheese, lettuce, tomato, onions, garlic, and a slather of tangy mayo? Double check. See you in line.
How to order: Stop by the original Logan Square or newer Lincoln Park location for onsite dining, delivery, and carry-out, or order online via GrubHub, Postmates, and Uber Eats.

Mapo tofu at Lao Sze Chuan

Multiple locations
Not for the faint of heart, this chili pepper-flecked pool of bubbling hot broth littered with molten globs of silky tofu and slices of crisp, bright green onions is Chinese comfort food in its purest—and most delicious—form. It’s no wonder this dish helped put Lao Sze Chuan on the map, launching it from a homey Chinatown operation in 1998 to a mini-empire with celebrated outposts across the Midwest.
How to order: Head to one of eight Chicagoland locations for onsite dining and carry-out or order delivery online via DoorDash, GrubHub, Postmates, and Uber Eats.

Conceptual cocktails at the Aviary

West Loop
While the pandemic and its continued fallout have all but squashed traditional fine dining, Alinea Group mastermind chef Grant Achatz is keeping his penchant for executing feats of molecular gastronomy brilliance alive and well over at this long running West Loop cocktail bar-slash-innovation hub. Reserve your socially distanced seat for an intricate six-, five-, or three-course tour of top shelf tipples engineered to tickle the imagination alongside a host of creative bar bites.
How to order: Hit up Tock for onsite dining reservations and curbside pick-up options.

Tavern-style pizza at Vito & Nick's 

As much as we enjoy the occasional deep dish excursion, us urbanites know that real Chicago pizza means square cut, cracker thin tavern-style. And there’s no better place to rev your authentic pizza engine than Vito & Nick’s, a South Side institution that’s been perfecting the crunchy, fully-loaded style since 1923. The crust hits the spot, for sure, but it’s the toppings, a broad expanse of meats, veggies, and palate-scorching giardiniera stretching all the way to the flawlessly blackened edge, that slyly steal the show.
How to order: Call 773-735-2050 or drop into the OG Pulaski pizzeria for onsite dining information and carry-out or order online via GrubHub.

Short rib beignets at Boeufhaus

West Town
“New Orleans-style beignets in all their dreamy, doughnut-y goodness, but make it savory,” that was the original impetus behind this rustic-chic Western Ave chophouse’s boundary-defying appetizer. And savory it became, a blanket of puffy deep-fried dough wrapped tightly around a generous wad of short rib, seasoned, seared, and braised until fork-tender. Swap the requisite powdered sugar for a ladleful of haus jus and you’re in business.
How to order: Order pick-up via Toast and keep an eye on the website for ongoing reopening updates.

Pierogi from Kasia’s Deli

Ukrainian Village
Consistently awarded the best pierogi in Chicago by countless area publications, this bustling Ukrainian Village counterserve lives up to the hype with their rotating cast of masterfully doughy Eastern European dumplings. With each bite, the soft, toothsome exterior gives way to piping hot fillings like potato and bacon, cabbage and onion, beef goulash, sauerkraut and Polish sausage, mushroom with pesto and truffles as well as sweet options like fresh strawberries, plums, and wild blueberries.
How to order: Check out the Chicago Avenue storefront for onsite dining and carry-out options or order online via Uber Eats and GrubHub.

Cowboy steak at RPM Steak

River North
Steakhouses are to Chicago as red sauce Italian joints are to New York and izakaya are to Tokyo—they’re simply embedded in the city’s dining DNA. See what all the meaty fuss is about in true go-big-or-go-home fashion with this hulking 24-ounce bone-in rib-eye from upmarket River North chophouse RPM, dry-aged for 28 days, peppered, salted, and expertly seared for a pleasantly smoky bite and velvety pink center. Life doesn’t get more *chef’s kiss emoji* than that.
How to order: Make a reservation for onsite dining and schedule carry-out through Tock or order pick-up and delivery online via ChowNow, Uber Eats, Postmates, Caviar, DoorDash, and GrubHub.

Carnitas at Carnitas Don Pedro

To claim that Don Pedro’s carnitas—knuckle-sized chunks of luscious pork, rife with crunchy chicharrón morsels, ambrosial caramelized fat, and pulpy shredded meat—stands as Chicago’s most coveted taco filling would be a grave understatement. Pick up a pound of the good stuff (alongside a stack of warm tortillas and a healthy sprinkling of chopped white onions, fresh cilantro, salsa, and lime, of course) on your way to the park and prepare to be the most popular guest at the socially-distanced picnic.
How to order: Pop by the storefront, order online, or call 312-829-4757 for carry-out, or cop delivery via Uber Eats.

Jim Vondruska/Thrillist

Breaded steak sandwich at Ricobene’s

Seasoned beef, lovingly breaded and fried for the ultimate crispy outside-tender inside combo is an unparalleled delight for the senses. As if that weren't enough, this revered South Side staple has been stuffing their perfected protein inside pillowy Turano French bread and layering the whole mess with gooey mozzarella and hot giardiniera since 1946. No wonder it’s been dubbed the best sandwich in the world by multiple publications.
How to order: Call 312-225-5555 or place your order online straight from the source.

Sign up here for our daily Chicago email and be the first to get all the food/drink/fun in town.

Our Newsletter
By Signing Up, I Agree to the Terms and Privacy Policy.