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10 Quintessentially Chicago Dishes and Where To Eat Them in the Windy City

Chow down on Chi-town’s best grub, from pizza to popcorn to pierogies in the city’s many neighborhoods.

deep dish pizza in chicago
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Liam Greenwell is a writer and teacher based in Mexico City. He is originally from Cambridge, Massachusetts. You can read more of his work at liamgreenwell.com and find him on Twitter @liam_greenwell.

The self-proclaimed “Second City” of the United States is home to plenty of proud locals who would claim their city actually is second to none. Chicago has plenty to brag about, such as world-class art, culturally rich neighborhoods, and, of course, a varied food scene featuring Michelin-star restaurants, hip neighborhood joints, and unassuming hidden gems. These are 10 iconic dishes that capture something of the city, past or present, all of which should encourage visitors to venture into Chicago’s many diverse areas, well beyond the Magnificent Mile.

1. Jibarito sandwich

Jibarito sandwich, Chicago cuisine
The jibarito sandwich is originally a Puerto Rican dish.Foto: Brent Hofacker / Shutterstock

Enjoy Puerto Rican cuisine in the heart of Chicago.

A great place to start your Chicago food tour is with an item that traces its origin to the neighborhood of Humboldt Park. In the mid-1990s, restaurateur Juan Figeroa had the bright idea to replace the bread on a steak sandwich with smashed fried plantains—a nod to his Puerto Rican origin—to give locals a taste of his home. These days, you'll find the jibarito sandwich throughout the city, including some inventive vegetarian riffs.

Where to try the jibarito in Chicago: Eat the sandwich at Figeroa’s restaurant in North Center, Borinquen, along with other delicious Puerto Rican plates like stuffed plantains or shrimp with tostones.

Related: How Chicago Became a Jibarito City (and Where To Get One)

2. Chicago popcorn

chicago popcorn in a bowl
You can also buy Garrett’s at both O'Hare and Midway if you forgot to stop by while you were in town.Foto: Brent Hofacker / Shutterstock

A sweet and salty confection.

A typical last-minute airport souvenir, Garrett’s Mix may not be on too many Chicagoans’ daily shopping lists, but it still holds a special place in many residents’ hearts. Named “Chicago Mix” until the company lost a trademark lawsuit regarding the name, the classic is a blend of caramel and cheddar cheese popcorn the perfect blend of savory and sweet.

Where to try Chicago popcorn in Chicago: You can find Garrett’s at Wrigley Field or one of three tourist-friendly Garrett Popcorn Shops in the Chicago Loop.

3. Ukrainian pierogies

Ukrainian pierogies, chicago
"Varenyky" is the Ukrainian word for pierogi.Foto: Brent Hofacker / Shutterstock

A part of Ukrainian culinary pride.

Chicago has one of the largest populations of Ukrainians in the US, and you’ll find the community’s fingerprints throughout the city’s culinary offerings. Varenyky is the Ukrainian name for pierogi, a potato and meat-stuffed dumpling topped with sour cream and green onions.

Where to try Ukrainian pierogies in Chicago: At Tryzub Ukrainian Kitchen pierogies are made in a variety of colors—the shells are dyed with beet, mushroom, and carrot. The restaurant, which is only a few blocks from the Ukrainian National Museum, serves muffed-up versions of classics like chicken Kiev and borscht. While you’re in West Town, explore the rest of Ukrainian Village and other neighborhoods on a walking tour.

4. Chicago-style hot dogs

Chicago-style hot dog
Do *not* put ketchup on a Chicago-style hot dog.Foto: Brent Hofacker / Shutterstock

Keep your ketchup at home.

A traditional Chicago dog features a grocery list of toppings: yellow mustard, relish, sliced tomato, a pickle spear, white onion, peppers, and celery salt on a poppy seed bun. Certain vendors may (or may not) advise swapping all of the above for sauerkraut or beef chili instead.

But one thing that’s never acceptable (at least, for anyone above the age of 10) is ketchup. In fact, don’t even glance at the red condiment dispenser (it’s there for fries, by the way) in hopes of using it on your dog.

Where to try Chicago-style hotdogs in Chicago: Sample one at the Wiener's Circle, which stays open until the wee hours of the morning, perfect for appeasing those late-night hunger pangs.

5. Tamales

Tamales in Chicago
Tamales are sold by street vendors or in restaurants in Chicago.Foto: Sergio Hayashi / Shutterstock

From sidewalk coolers to brick-and-mortar.

The varieties of tamales are endless, from those steamed in corn husks and filled with mole to ones in banana leaf featuring a pudding-like creamy mix inside. They’ve been around Chicago for decades as a fixture of the city’s Mexican-American culinary output. But one man in particular gained recognition for his direct-to-consumer business model. Claudio Vélez made his name hawking tamales out of a red cooler outside popular bars as a restorative, post-boozing snack.

Where to try tamales in Chicago: These days, you can visit his physical storefront in Avondale if you don’t want to play the game of chance—or the Oaxacan restaurant Kie-Gol-Lanee in Uptown if you’d prefer the banana leaf version.

6. Deep dish pizza

Chicago deep dish pizza
Deep dish pizza is deeply dividing.Foto: Brent Hofacker / Shutterstock

Tourist trap or worthy pie?

New Yorkers are quick to protest that Chicago deep dish “isn’t even pizza,” but that doesn’t stop locals and tourists alike from seeking out this gooey source of local pride on a regular basis. Bring your fork and knife and come with an empty stomach—each pie is a bathtub of cheese and sauce with a delicious, buttery crust, enough to satiate even the hungriest diners.

Where to try deep dish pizza in Chicago: One classic spot is Pequod’s Pizza, but you can also venture north for a refined take at Burt’s Place in the northern suburbs. You can also learn how to cook your own version after sampling the local offerings.

Related: Have a Real Slice Time on These US Pizza Experiences

7. Italian beef sandwich

Italian beef sandwich in chicago
If you haven't seen "The Bear," you might not know about this sandwich.Foto: Brent Hofacker / Shutterstock

A beloved classic made famous by a TV series.

Perhaps a bit more under the radar than deep dish pizza and Chicago dogs before the release of The Bear, the recent television show has vaulted this humble but delicious sandwich into superstardom. Skip the fancy knockoffs trying to capitalize on the show’s success and head to an old-fashioned beef stand—the good ones make their own giardiniera, an Italian pickled mix of vegetables.

Where to try an Italian beef sandwich in Chicago: Check out a few on a food tour, or head directly to West Town, where the deli Bari Subs makes a killer Italian beef sandwich. Plus, they have a variety of other options for vegetarians, too.

8. Flaming saganaki

Flaming saganaki in Chicago
This dish was originally just a marketing ploy—but it worked.Foto: Adam Madey / Shutterstock

Perfect for both substance and style.

Birthed in an effort to attract clientele, the flaming saganaki came out of the Parthenon restaurant in Greektown in 1968. That year, a server decided to flambé the traditional Greek cheese saganaki tableside. With a shout of “Opa!,” a Greek phrase expressing excitement, what could have been a fiery disaster became a staple of the neighborhood.

Where to try flaming saganaki in Chicago: This isn’t one to make at home (or to find in Greece, for that matter)—it’s best to enjoy it at one of the many Greektown restaurants in the Windy City.

9. Rib tips

Rib tips, chicago barbecue
Chicago does barbecue its own way.Foto: hlphoto / Shutterstock

Carnivores should chow down on BBQ from the South Side.

Good barbecue doesn’t only exist south of the Mason-Dixon line. In fact, Chicago has a deep soul food heritage, as African American chefs brought their recipes to the city during the Great Migration and have iterated on them since.

Rib tips are a menu item you won’t find in Kansas City or Charlotte: They’re the ends of spare ribs that are often thrown away. In Chicago, though, locals like the contrast of the burnt outside and cartilaginous interior and typically pair them with a hot link doused in sauce.

Where to try rib tips in Chicago: The South Side has plenty of good places to try them but start at Lem’s Bar-B-Q, a beloved standing-room-only eatery in Greater Grand Crossing. Make sure to learn more about the area’s African American history with a tour of the South Side while you’re there.

10. Malört

Malört in Chicago
Only the brave will drink Malört.Foto: BrandonKleinPhoto / Shutterstock

Try it if you dare.

Much maligned and deeply loved, Malört is something Chicagoans will insist you try before spitting it out themselves. It’s a masochistic tipple—the herbaceous taste doesn’t even begin to describe it—that includes ingredients like wormwood, anise, gentian root, and many more of the most controversial flavors in the world, all mixed up into a slime-green spirit.

Where to try Malört in Chicago: Make sure you drink the real stuff (Jeppson’s), preferably at a dive like Richard’s Bar, where drinkers still puff Pall Malls despite the 2008 indoor smoking ban. It’s the perfect way to end your visit and digest (or not) all the food you’ve eaten so far.

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