Chicago is a culinary playground with a diverse array of eats and drinks that reflect the city’s rich culture and innovative food scene. From deep-dish pizza to inventive cocktails, this list celebrates the iconic, indulgent, and must-try experiences for food lovers in the Windy City. Whether you’re a Chicago native or a first-time visitor, these 16 food and drink items promise to take your taste buds on a memorable journey.
1. Deep-Dish Pizza at Lou Malnati’s
Chicago’s deep-dish pizza is legendary, and Lou Malnati’s is a gold standard. With a buttery crust, tangy tomato sauce, and layers of gooey cheese, every bite is a testament to Chicago’s pizza prowess. Pair it with a cold beer for a quintessential Chicago experience.
2. Chicago-Style Hot Dog at Portillo’s
A Chicago-style hot dog is an all-beef frank loaded with mustard, onions, relish, pickles, tomatoes, sport peppers, and celery salt on a poppy seed bun. Portillo’s serves one of the city’s best versions of this local favorite. Just remember, no ketchup allowed!
3. Italian Beef Sandwich at Al’s Beef
The Italian beef sandwich is a messy, savory delight. Thinly sliced beef soaked in au jus, topped with giardiniera, and served on a fresh roll—it’s a flavor-packed meal. Go for it “dipped” for the ultimate juicy experience.
4. Garrett Mix Popcorn from Garrett Popcorn Shops
Garrett Popcorn’s iconic mix of caramel and cheddar popcorn is an addictive snack. The salty-sweet combination has been winning over Chicagoans and tourists alike since 1949. Pick up a tin to share—or keep it all for yourself.
5. Cheeseburger at Au Cheval
Au Cheval’s cheeseburger is a masterpiece of simplicity done exceptionally well. The thick patties, melted cheese, and perfectly toasted bun create an unforgettable bite. Add a fried egg or thick-cut bacon for an even more indulgent treat.
6. Jibarito at Borinquen Lounge
This Puerto Rican sandwich replaces bread with crispy fried plantains, stuffed with steak, cheese, lettuce, and garlic mayo. It’s a unique Chicago invention that reflects the city’s vibrant Puerto Rican community. Borinquen Lounge is said to be the birthplace of this flavorful creation.
7. Rainbow Cone from Original Rainbow Cone
The Rainbow Cone is a nostalgic dessert featuring five colorful layers of ice cream: orange sherbet, pistachio, Palmer House, strawberry, and chocolate. Each layer brings a unique flavor and texture, making every bite a delightful surprise. It’s a must-try during Chicago summers.
8. Malört
Malört is Chicago’s infamous herbal liqueur with a strong, bitter flavor that’s not for the faint of heart. Locals and visitors alike take pride in “surviving” their first shot. It’s an acquired taste, but trying it is a rite of passage.
9. Cinnamon Rolls at Ann Sather
Ann Sather’s cinnamon rolls are a sweet, sticky delight and a Chicago breakfast institution. These oversized pastries are soft, gooey, and generously slathered with icing. They’re perfect on their own or as a complement to a hearty brunch.
10. Fried Chicken at Harold’s Chicken Shack
Harold’s Chicken Shack has been serving crispy, flavorful fried chicken for decades. Its signature mild or hot sauce adds a tangy kick that elevates every bite. Pair it with fries and coleslaw for the ultimate comfort meal.
11. Duck Fat Fries at The Purple Pig
The Purple Pig’s duck fat fries are golden, crispy perfection. The rich flavor from the duck fat makes these fries stand out among the competition. Served with a side of aioli, they’re a decadent treat.
12. Smoked Fish from Calumet Fisheries
Calumet Fisheries specializes in expertly smoked fish, from salmon to shrimp. Located on Chicago’s Southeast Side, it’s a James Beard Award-winning gem. The fish’s smoky flavor and tender texture are worth the trip.
13. Ramen at Wasabi
Wasabi serves up some of the best ramen in Chicago, with rich broths and perfectly cooked noodles. Their Tonkotsu Ramen, with pork belly and soft-boiled egg, is a fan favorite. It’s the perfect comfort food on a chilly Chicago day.
14. Donuts at Do-Rite Donuts
Do-Rite Donuts crafts small-batch donuts in creative flavors like candied maple bacon and pistachio-Meyer lemon. Their donuts are light, fluffy, and worth the hype. Pair one with their excellent coffee for a satisfying breakfast or snack.
15. Steak and Dirty Martini at Gibson’s Bar & Steakhouse
Gibson’s is a Chicago institution for a reason—its steaks are top-notch. The USDA Prime cuts are cooked to perfection and served in a classic steakhouse setting. Save room for their giant desserts, like the chocolate mousse pie.
16. Cocktail at The Aviary
The Aviary takes mixology to an art form with its innovative cocktails. Each drink is a sensory experience, often incorporating unexpected techniques and presentations. Sip on creations like the “In the Rocks,” a cocktail encased in an ice sphere.
Chicago’s food and drink scene is as dynamic and diverse as the city itself. Whether you’re indulging in iconic deep-dish pizza or savoring the artistry of a Michelin-starred meal, there’s always something delicious waiting to be discovered. Add these 20 must-tries to your Chicago itinerary and enjoy every flavorful moment.
What Are the Other Best Foodie Cities in the USA?
The United States is a melting pot of cultures, and its food scene is a perfect reflection of that diversity! From coast to coast, you’ll find cities that have mastered their local cuisine and embraced international flavors. Can you guess the others??