The Italian beef sandwich is another Chicago staple, dating back to Italian American immigrants in the early 20th century. The iconic sandwich includes tender and juicy roast beef on a soft roll, dipped in flavorful light broth or gravy.

The sandwich can be topped with sweet peppers or giardiniera, Italian pickled vegetables mixed in oil. Hit up a favorite local spot, Al’s Beef on Taylor Street, for this must-try Chicago food. You can also meander over to Johnnie’s Beef in Elmwood Park, or Mr. Beef, the classic restaurant where the popular Hulu show “The Bear” is filmed. 

4. Jibarito

The jibarito is a delicious local creation from Chicago’s Puerto Rican communities. The iconic sandwich was created by Juan Figueroa in the 1990s. It consists of sliced and fried plantains, your choice of seafood, meat, or vegetables, and lettuce, mayo, and cheese on top. These days, you can find the jibarito sandwich throughout the city, with some tasty and inventive vegetarian versions. Try the jibarito at Figueroa’s Borinquen Restaurant in Humboldt Park, or La Bomba in Logan Square.

5. Chicago-Style Popcorn

In 1949, you could snag a bag of flavored popcorn from Garrett Popcorn Shop’s founder, Gladys Otto Garrett, for 5 cents on Chicago’s streets. Today, these tasty treats are still made in copper kettles like they were three generations ago. The most notable handcrafted recipe combines caramel and cheese popcorn for a sweet-and-savory snack, a nostalgic and well-loved Windy City classic today. You can try out Chicago-style popcorn at any of the Garrett Popcorn Shops in the Chicago Loop.

Tips for Enjoying Chicago’s Iconic Foods 

To fully enjoy Chicago’s traditional dishes, follow these tips for local, hidden gems, how to order like a true Chicagoan, and seasonal food festivals to check out: 

Seek out Hidden Gems

Many locals will direct you to hidden gems in neighborhoods like Chinatown, Logan Square, Devon Avenue, and Pilsen. Each offers its own unique, authentic culinary experience beyond the mainstream deep-dish pizza or hot dogs. Devon Avenue features South Asian cuisine, for instance, while you’ll find delicious Mexican food in Pilsen. Locals also turn to old-fashioned Italian beef stands or delis in Little Italy for the best sandwiches in the city, where they make their giardiniera fresh.  

Explore Neighborhood Food Festivals

For a deeper dive into Chicago’s culinary culture, check out the city’s food festivals. Popular options include Taste of Chicago, a famous yearly food festival, and its neighborhood pop-ups, like those in Pullman, Albany, and Marquette Park.

For an authentic local experience, look for smaller, neighborhood-focused festivals. These celebrate specific cuisines or culinary themes, like Taste of Fulton Market, Lakeview Taco Fest, and Taste of Randolph.

Order Like a Chicagoan

Order the best Chicago dishes like a local. When you’re in the mood for a Chicago-style hot dog, order it “dragged through the garden,” which means you want all the fixings. When grabbing an Italian beef sandwich, ask for it “dry” or “wet” if you want it dipped in gravy.

The most loved deep-dish pizza options are the classic or original style, but you can also choose pan or stuffed, or even request well-done for an extra crunch or caramelized edge. Many Chicagoans also enjoy tavern-style, a cracker-thin crust pizza that comes in square or “party cut” slices, often paired with a beer.  

Seek Guidance From a Registered Dietitian Nutritionist

For more help on your food journey across the Windy City, seek guidance from a Registered Dietitian. They’ll help you enjoy your deep-dish, dogs, and festivals by offering practical dining-out and travel strategies for your goals. At Doherty Nutrition, our team can provide intuitive and mindful eating guidance, so you can build confidence and balance as you navigate the city’s rich culinary scene. 

Savor Chicago by Balancing Your Iconic Bites

From deep-dish pizza and topping-packed Chicago dogs to juicy Italian beef, crisp jibaritos, and sweet-savory Chicago-style popcorn, these classics tell the city’s story. Explore neighborhood gems and seasonal festivals to taste the diversity behind every bite. Enjoy what you love and feel great doing it — no food rules required. 

When you’re ready to find a balance that fits your life, turn to Doherty Nutrition. Our Registered Dietitian Nutritionists offer simple, sustainable guidance for dining out, traveling, and everyday meals. To get started, book a consultation with us today. Enjoy a true Chicago food experience, where you approach every bite in a balanced, mindful way that fits your life.