18 Chicago Foods Fit For The First Windy City Pope

Chicago’s culinary landscape is as diverse as it is delicious, and it’s no surprise that the Windy City offers an array of iconic foods that could satisfy even the most discerning palate. From deep-dish pizza to the city’s take on a classic hot dog, these 18 Chicago foods are not only a testament to the city’s rich cultural tapestry but also a gastronomic delight fit for the first Windy City Pope. Each item tells a story, offering a taste of Chicago’s vibrant neighborhoods and history.

1. Deep Dish Pizza

Deep Dish Pizza
© Concierge Preferred

What makes a Chicago deep-dish pizza holy is its sheer depth of flavor and texture. Imagine sinking your teeth into layers upon layers of gooey mozzarella cheese, topped with a chunky tomato sauce that sings with the sweetness of ripe tomatoes. The buttery crust holds it all together, creating a pizza that’s more like a pie.

Lou Malnati’s or Pequod’s are the anointed places for this divine dish. Whether gathered around a bustling table with friends or savoring a slice alone, deep-dish pizza is an experience that demands reverence. It’s a taste of Chicago’s heart.

2. Italian Beef Sandwich

Italian Beef Sandwich
© Mezzetta

The Italian beef sandwich is a rite of passage for any Chicagoan. Thin slices of seasoned beef are soaked in a flavorful jus, served on a fresh roll that absorbs all those savory juices. Add in sweet and hot peppers, and you have a handheld feast.

Messy? Absolutely, but it’s that delicious chaos that makes it irresistible. Whether you prefer it dipped or dry, this sandwich offers a taste explosion that’s worth the mess. It’s a staple in Chicago’s food scene, a true culinary blessing.

3. Chicago-Style Hot Dog

Chicago-Style Hot Dog
© The Kitchn

In Chicago, a hot dog is more than just a snack; it’s a tradition. The Chicago-style hot dog is an all-beef frankfurter served on a poppy seed bun and topped with a symphony of flavors. Mustard, neon green relish, onions, tomatoes, a pickle spear, sport peppers, and a sprinkle of celery salt complete the ensemble.

The cardinal rule? No ketchup, ever. This hot dog is a celebration of taste and texture, offering a delightful crunch and zing that epitomizes Chicago’s culinary creativity.

4. Jibarito Sandwich

Jibarito Sandwich
© Tasting Table

A heavenly fusion of flavors, the jibarito sandwich swaps bread for crispy, fried plantains, creating a unique culinary experience. Filled with savory steak, garlic mayo, and a hint of spice, it’s a testament to Puerto Rican creativity within Chicago’s diverse culinary landscape.

The textures intertwine harmoniously, with the plantains providing a satisfying crunch against the juicy steak. Every bite is a blend of savory and sweet, a sandwich that breaks the mold and offers a taste of innovation that feels like a divine revelation.

5. Maxwell Street Polish Sausage

Maxwell Street Polish Sausage
© Portillo’s

Late-night cravings find salvation in the form of the Maxwell Street Polish sausage. Served hot off the grill, this sausage is topped with caramelized onions and a smear of mustard, all cradled in a soft bun.

Its origins trace back to Chicago’s Maxwell Street market, where it became a beloved staple. The sausage itself is snappy and flavorful, a satisfying meal that warms both the stomach and the soul. In the heart of the city, it remains a flavorful tribute to Chicago’s multicultural heritage.

6. Chicago Mix Popcorn

Chicago Mix Popcorn
© Garrett Popcorn Shops

Sweet meets savory in the beloved Chicago mix popcorn, a treat that combines the best of both worlds. Imagine biting into the cheesy crunch of cheese popcorn, followed by the buttery sweetness of caramel popcorn—each bite a delightful contrast.

Chicagoans often turn to this snack when in need of comfort, offering both sin and salvation in every handful. Created by Garrett’s, it has become an iconic snack, bridging flavors in a way that feels almost magical. It’s a perfect reflection of Chicago’s eclectic palate.

7. Rainbow Cone

Rainbow Cone
© The Original Rainbow Cone

The Rainbow Cone is not just ice cream; it’s a celebration of color and flavor. With five layers—chocolate, strawberry, Palmer House, pistachio, and orange sherbet—each scoop tells its own story.

This nostalgic treat is a staple at summer outings in Chicago’s parks. The combination of flavors offers a unique tasting journey that delights both young and old. It’s a colorful reminder of childhood joy and the simple pleasures of life, making it a must-try for anyone visiting the Windy City.

8. Tamales from a Street Cart

Tamales from a Street Cart
© Reddit

Simple yet satisfying, tamales from a Chicago street cart bring a taste of authenticity to the city’s diverse food scene. Made with masa dough and filled with meats or cheeses, they are wrapped in corn husks and steamed to perfection.

Each bite offers a soft, flavorful experience, often accompanied by a dash of hot sauce for extra zest. The street cart tamale is a no-frills delight, perfect for a quick, satisfying meal on the go, embodying the spirit of Chicago’s vibrant street food culture.

9. South Side Fried Chicken

South Side Fried Chicken
© Eater Chicago

Harold’s Chicken Shack is an institution on Chicago’s South Side, known for its perfectly fried chicken. Crispy on the outside, juicy on the inside, and drenched in a signature mild sauce, this dish is a local favorite.

Served alongside slices of white bread, it’s the kind of comfort food that brings people together. The experience of savoring Harold’s fried chicken is almost ceremonial, a flavor-packed homage to the city’s culinary traditions, offering warmth and satisfaction in every bite.

10. Butter-Crust Tavern Pizza

Butter-Crust Tavern Pizza
© Brian Lagerstrom

South Side thin crust pizza is a testament to Chicago’s love affair with pizza. The butter-crust tavern pizza, cut into squares, offers a crunchy delight with each bite. Topped with a rich layer of cheese and your choice of toppings, it’s a versatile dish perfect for sharing.

Best enjoyed in the company of friends and a cold drink, this style of pizza is a staple in local taverns. Its crispy edges and buttery crust make it a beloved choice for pizza lovers across the city.

11. Malört

Malört
© Liquor.com

For the uninitiated, Malört is more an experience than a drink—a bitter, herbal spirit that Chicagoans embrace with pride. Known for its bold, challenging flavor, it’s often regarded as a rite of passage in the city.

Whether loved or loathed, a sip of Malört is a conversation starter, a quirky part of Chicago’s drinking culture. It’s a tradition that binds the community, offering a taste of the city’s adventurous spirit. Trying it is a must, even if it’s just for bragging rights.

12. Skillet Corned Beef Hash

Skillet Corned Beef Hash
© Sugar and Soul

A staple of Chicago’s old-school diners, skillet corned beef hash is a comforting start to any day. Crispy edges of corned beef mixed with soft, seasoned potatoes create a harmonious blend of flavors and textures.

Topped with two perfectly cooked eggs, it’s a dish that promises satisfaction and warmth. Served in a cast-iron skillet, the hash is a nod to classic American breakfast traditions, with a touch of Chicago’s own flair. It’s a hearty meal that soothes the soul.

13. Steak from Gene & Georgetti

Steak from Gene & Georgetti
© Gene And Georgetti

Steak at Gene & Georgetti is more than just a meal; it’s an experience steeped in tradition. Chicago’s oldest steakhouse offers cuts that are perfectly seared, juicy, and full of flavor.

Served in a classic setting with white tablecloths, the steak is complemented by traditional sides like creamy mashed potatoes. Whether dining with family or celebrating a special occasion, a steak from Gene & Georgetti is a taste of Chicago’s culinary elegance, embodying the city’s love for quality and tradition.

14. Flaming Saganaki

Flaming Saganaki
© Better Magazine

OPA! The exclamation heard throughout Greektown when flaming saganaki is served. This dramatic dish features cheese set aflame tableside, creating an impressive spectacle.

Doused with a squeeze of lemon, the cheese becomes a melty delight, offering a taste as bold as its presentation. Enjoying this dish is a communal experience, a perfect blend of flavor and fun that captures the lively spirit of Chicago’s Greektown.

15. Churros from Maxwell Street Market

Churros from Maxwell Street Market
© Newcity Resto

Warm, crispy, and sweet, churros from Maxwell Street Market are a delightful street treat. Coated in cinnamon sugar, they offer a simple yet satisfying dessert experience.

Perfect for enjoying while exploring the vibrant market, these churros bring a touch of Latin flavor to Chicago’s diverse food scene. Their sweet aroma and satisfying crunch make them an irresistible choice for anyone with a sweet tooth.

16. Paczki

Paczki
© Eater

Paczki are more than just doughnuts; they’re a Polish tradition celebrated throughout Chicago. These rich, jam-filled pastries are especially popular on Fat Tuesday, when the city indulges in their sweet, fruity goodness.

Dusted with powdered sugar, each paczek offers a burst of flavor and a nod to the city’s Polish heritage. Whether enjoyed with coffee or as a standalone treat, they provide a sweet escape, perfect for those looking to savor a taste of tradition.

17. Chicken Vesuvio

Chicken Vesuvio
© Damn Delicious

Chicken Vesuvio is a dish that sings with the flavors of garlic, wine, and herbs. This classic Chicago creation features chicken and potatoes baked until golden in a savory sauce.

The aromas are intoxicating, each bite offering a taste of comfort and sophistication. Often served in Italian restaurants, it’s a testament to Chicago’s love for hearty, flavorful dishes that bring people together around the table.

18. Cheeseburger from Au Cheval

Cheeseburger from Au Cheval
© Business Insider

Heralded as one of the best burgers in the country, the cheeseburger from Au Cheval is a masterpiece of simplicity and taste. With layers of melted cheese, crispy bacon, and a perfectly cooked patty, it’s a burger that deserves its own accolades.

Each bite is an umami explosion, a comfort food classic elevated to new heights. Served in a stylish diner setting, it’s a quintessential Chicago experience that promises satisfaction to all burger aficionados.