As TV drama The Bear continues to tantalise the taste buds of viewers around the globe, there’s one American city on every food lover's lips right now: Chicago. But there’s much more to it than what you may have seen on screen; while it’s famed for deep-dish pizzas and Italian beef sandwiches, the USA’s Second City has far more to offer than carb-loaded comfort fare (though of course, there’s that, too – and it’s every bit as delicious as it looks). Planning a trip? Feast your eyes on our ultimate list of must-try food and drink experiences.
Click or scroll through our gallery to discover 23 gastronomic experiences you simply must try when in Chicago, counting down to the most unmissable of all.
Sometimes, only fried food will do – and if you’re feeling the urge, we recommend that you get yourself to one of Parson’s three Chicago locations, pronto. As you may have guessed from the name, this mini-chain specialises in two things: fried chicken (served straight up with white bread and pickles, loaded into a range of sandwiches, or perched on a Belgian waffle) and fried fish (get yours in a sandwich or multi-piece basket).
While it isn’t quite as picturesque as the real Portofino, this breezy restaurant’s fantastic riverfront location certainly gives the sun-soaked Italian city a run for its money. Grab a table on the all-weather patio and get ready for a feast; the menu is filled with the likes of shareable antipasti, fresher-than-fresh salads, hand-stretched pizzas, exquisite pastas and charcoal-grilled seafood dishes – and you’ll want to try a little bit of everything.
Situated close to the Theatre District in the centre of the bustling Loop, The Dearborn is a sophisticated, booth-filled beacon of classic American fare that’s perfect for a post-matinée meal. The menu is filled with sumptuous staples like Midwestern fried chicken, tavern-style pizza and Chicago’s finest fish and chips (made famous by the restaurant’s chef, Aaron Cuschieri, on TV show Beat Bobby Flay). But it’s the steak here that really shines; choose from bavette, New York strip, rib-eye or filet mignon, all of which come cooked to perfection – with house-made mashed potatoes and your choice of sauce on the side.
Though its interiors are thoroughly modern (not to mention effortlessly stylish), La Josie is a restaurant dedicated to bringing only the most traditional and time-tested of Jaliscan recipes to Chicago’s West Loop. Here, you can dig into fresh, fruity ceviche, fully loaded enchiladas and a range of meticulously made tacos – a favourite of which comes filled with tender Amish chicken, roasted jalapeños and smoked bacon mojo. La Josie is also home to not one, not two, but three agave bars, one of which is on the roof.
If you want to complete a culinary tour of Chicago, Chinatown is a must-visit; filled with snack shops, teahouses and dim sum restaurants, it’s the second-largest Chinatown in the US. That said, the never-ending choice of Chinese eateries can be a little overwhelming – so, if you’d like to cut to the chase, grab yourself a table at Xi’an Cuisine. This sought-after spot (which also has a West Loop location) is renowned for its hand-stretched noodles, which are crafted into an array of soups and lo mein dishes. Our tip? Try a Chinese hamburger: soft, tender meat stuffed inside a fluffy bao bun.
Don’t be fooled by the sleek booths, spinning chrome bar stools and mini jukeboxes – despite its classic looks, the Little Goat is a thoroughly modern take on the great American diner. Run by James Beard Award–winning chef Stephanie Izard, it doles out dishes that are a cut above your regular cafeteria fare; think Sichuan pork sausage served up on a spring onion and Cheddar biscuit, and okonomiyaki pancakes topped with bacon, a fried egg and crunchy bonito flakes. Of course, if you’re hankering after some traditional comfort food, there’s that, too. Corned beef hash or syrupy pancakes, anyone?
If you’re visiting Chicago, you simply must swing by one of its fabled blues bars – and Rosa’s is among the most atmospheric of the lot. A joint that encourages both traditional and modern performers to its stage, it’s owned by Tony Manguillo, an Italian immigrant who was inspired to come to the city in 1978 after meeting blues musicians Junior Wells and Buddy Guy in Milan. Filled with memorabilia, the cosy spot is a tribute to the south-side blues clubs of old, and it’s a great place to get lost in melody after soulful melody as you sip on an expertly made drink.
From the outside, you’d never guess that the building at 2515 South Wabash Avenue is home to the world’s first two Michelin star brewery. However, by the time you’ve passed through the waiting area, up the stairs and past a TV-shaped window offering cinematic views into the kitchen, you’ll be convinced that you’re about to experience something special. In the intimate dining room, you can delve into a hyper-seasonal tasting menu complete with impeccable beer pairings – but if you’re after something more casual, you can order à la carte delicacies like Hokkaido sea scallop and bone-in pork chop at the bar.
In a city so brimming with foodie delights, sometimes it’s difficult to know where to begin. When you’re in a culinary quandary, we say make your way to Time Out Market, an expansive brick building in the heart of the Fulton Market district. Cluttered with communal tables and swathed in string lights, this suits-all food hall brings together Chicago’s best-rated restaurants and most talented chefs under one roof – and every dish, from Urbanbelly’s pillowy dumplings to Sporty Bird’s fried chicken (the brainchild of James Beard Foundation Award–winning chef Art Smith), is handpicked by a team of local experts.
Sure, Chicago may be better known for its deep-dish and tavern-style pizzas – but that doesn’t mean the city doesn’t know how to make a mean slice of thin crust. For the best around, head to Logan Square’s Pizza Lobo, a photogenic old-school tavern that you may recognise from FX’s The Bear. Here, you can get your hands on tasty pies like the Fullerton Ave (vodka sauce, shredded mozzarella, sausage and pickled cherry peppers) and a range of straight-up slices, including cheese, pepperoni and the mysterious IYKYK (‘if you know, you know’).
A softly lit space decked out with dark wood, leather booths and all manner of curious knickknacks, The Chicago Athletic Association’s James Beard Award–winning Cherry Circle Room blends the historic building’s original features with elegant contemporary touches – and it has a menu of modern classics to match. If you really want to go to town, order the elaborate two-tier CCR Seafood Tower, a 30-day dry-aged ribeye steak or the Juicy Lisette: a half-pound wild game burger topped with chèvre cheese, blackberry jam and beef fat onions, accompanied by fries and bordelaise sauce.
There are plenty of places to get a fix of fantastic Italian food in Chicago – but if you’re after a cosy neighbourhood joint complete with heaving portions and a hearty side of good old-fashioned hospitality, La Scarola should be at the top of your to-do list. The dishes served here are just the type of meaty, cheesy, red sauce–covered classics we all crave every once in a while. Kitted out with white tablecloths, daintily folded napkins and celebrity photographs on every wall, it oozes old-school charm.
When sugar cravings strike, do as the locals do and head to Roeser’s. It’s Chicago’s oldest family-run bakery still in its original location, having been operated by four generations of Roesers since 1911 – and it’s famous throughout the city for its amazing custom-made celebration cakes. However, for a sweet treat on the go, you can’t beat one of the shop’s delicious doughnuts, which come in varieties like chocolate and salted caramel (not to mention a gloriously sticky glazed strawberry variety). A word of warning: you’ll need a napkin!
Classy West Loop bistro Au Cheval’s elevated take on the cheeseburger was once voted the best in America by Bon Appétit magazine – and when you take a bite, you’ll see why. Made using top-quality beef, the patties are cooked on a griddle until medium, layered with Kraft American cheese, then left to rest. After being loaded into a toasted bun, each burger is dressed with Dijonnaise and house-made pickles, with the option to add a fried egg, grilled bacon or, if you really want to push the boat out, foie gras. Those who’ve tried it say it’s a taste sensation.
We’ve covered the high-end option – now it’s time to tick off the type of cheap and cheerful burger you’ll want to eat with your hands. Redhot Ranch is a hot dog stand situated in the shadow of the Chicago White Sox’s Guaranteed Rate baseball field, and it’s the ultimate place to go for a late-night bite to eat. The RHR Cheeseburger served here isn’t only deeply satisfying, but it’s an absolute steal, too; for just a few dollars, you’ll get a griddled patty, melted cheese, lettuce, tomato, onion and special sauce in a pillowy bun, plus a free side of fries.
Designed to be cut into small squares and shared, tavern-style pizza – the city’s signature spin on the thin-crust pie – may be less famous than its deep-pan sibling, but it’s every bit as tasty. For the finest around, set a course for Vito & Nick’s Pizzeria, a spot in the Ashburn district that’s been throwing a range of bubbling, cheese-covered pizzas with cracker-thin crusts since the 1960s. With wood-panelled walls, neon beer signs and drop ceilings (and with Bears games often blasting from the TV), it’s a captivating window into the Chicago of years gone by.
With spectacular views of Millennium Park, the Art Institute and the captivating blue of Lake Michigan (which is, at times, indiscernible from the sky), Cindy’s – the Chicago Athletic Association’s rooftop restaurant – is the best place in town for a sundown supper. Under the supervision of executive chef Kaleena Bliss (a former Top Chef contestant, no less), the kitchen crafts delightful dishes from the freshest of local produce; think green curry prawns, whole fried branzino sea bass and sweetcorn campanelle (a type of pasta).
A veteran candy shop and ice cream parlour – with the old-fashioned booths, celebrity memorabilia and marble soda fountain to prove it – the original Margie’s Candies has been satisfying the sweet tooths of sundae-loving Chicagoans since 1921. Still run by the same family, the spot has been making its confections the same way for over a hundred years, and even The Beatles have had a taste (there’s a photo on display commemorating their 1965 drop-in). Served in a clamshell bowl with gravy boats of hot fudge and caramel on the side, the Turtle Sundae is a must-try.
What better way to spend a summer’s day in Chicago than by indulging in the three Bs: barbecue, beer and bands? Taking place every July outside the iconic United Center arena, the Windy City Smokeout is a four-day celebration of all things great and grilled, with a side of stellar country music thrown in for good measure. The west end of the festival is lined with stalls selling the most brilliant barbecue food from across the States – including famous fare like Joe’s Kansas City Bar-B Que’s Z-Man brisket sandwich, and Salt Lick’s succulent beef and pork sausage (a Texan favourite).
If your idea of hot dog heaven is a plain roll, a simple banger and a squirt of ketchup, this hefty handheld perhaps isn’t for you. However, if you like to load on the toppings, you’ll love Chicago’s decadent home-grown dog – featuring a beef sausage, mustard, onions, a pickle spear, sport peppers (medium-hot chillies), tomato and a sprinkle of celery salt on a poppy-seed bun. The story goes that the maximalist mouthful evolved from the ‘Depression dog’, a thrifty hot dog invented during the economic crash in 1929. These days, Norwood Park’s Superdawg Drive-In serves the best Chicago-style hot dogs around.
Quintessentially Chicagoan, deep-dish pizza is said to have been invented by Ike Sewell, the founder of Uno Pizzeria, back in 1943. While Uno is still a popular place to try the pie, Pequod’s – named the best pizzeria in the US by Yelp in 2024 – is currently the talk of the town. Though it’s been serving pizzas since the 1970s, a 2023 appearance in The Bear propelled the restaurant to international fame. Cradled by a caramelised cheese crust, the joint’s perfect pizzas are packed with layers of delicious fillings and come in four different sizes, depending on how hungry you are.
The Bear – a comedy-drama about a chef who returns to Chicago to run his family’s sandwich shop – is one of the hottest shows on the planet right now. Whether you’re an avid viewer or you’ve never seen an episode, Yes, Chef! Chicago: A Bear-Inspired Food Tour is a mouth-watering way to while away a few hours in the city. Travelling by air-conditioned bus, you’ll sample the flavours of Logan Square, River North and the West Loop, stopping off at filming locations and other recommended eateries, including Mr. Beef: the sandwich joint that started it all.
Want to get your hands on a bona fide Chicago icon? Make a beeline for Mr. Beef. This cozy joint has been slinging Italian beef sandwiches for over 40 years, and its contributions to the city’s culinary landscape haven’t gone unnoticed; the shop has reached dizzy heights in recent years, serving as the inspiration behind FX’s smash-hit show The Bear. The sandwiches here are gloriously messy, consisting of wet-roasted, thinly sliced beef, served on a French roll smothered in cooking juices – and they come either sweet (with sweet peppers) or hot (with spicy giardiniera).
A former private members’ club housed in a late 19th-century Venetian Gothic–style building, the Chicago Athletic Association’s ballrooms and bars were once reserved only for the privileged elite – but since it became a hotel in 2007, everyone has been welcome here. A piece of living, breathing history on the doorstep of Millennium Park in the city’s Central Loop, it’s an achingly cool place to stay, with luxurious vintage-inspired furnishings, comprehensive concierge services, 24-hour fitness facilities and no less than seven of its own dining establishments. Rooms start from $279 (around £215) per night.
Our writer stayed at the Chicago Athletic Association as a guest of Choose Chicago. For more information on Chicago, visit the Choose Chicago website.
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