Great Eats from the ‘Windy City’

From sizzling sandwiches to thick, deep-dish pizza – these 12 Chicago treats are classic.

Deep-Dish Pizza

More like a pie than a pizza, it takes 45 minutes alone to bake. Made in a deep pan to form a thick, flaky crust, this Chicago classic includes popular toppings like sausage, mushrooms and spinach layered up to the edges. Chunky tomato sauce is always added so the pizza can cook longer without burning the other ingredients. Think of it as an upside-down pizza!

Local tip: This is no ordinary pizza, so don’t try eating it with your hands. Do as the locals do and use a knife and fork.

Jibarito (Fried Plantains Sandwich)

Who wants a sandwich made with bread, when you can have crispy plantains instead? The restaurateur who created this fast-food favorite, was inspired by a Puerto Rican recipe that substituted bread for plantains. Green plantains are flattened and fried, making the perfect base for a generous filling. It’s piled high with lettuce, tomato, cheese and your choice of chicken, pork or steak – with steak being the original and probably the most popular one. There’s a vegetarian option, too!

Local tip: Humboldt Park, where this sandwich was first introduced to the city, is still one of the best places to try it.

Chicken Vesuvio

Sizzling in a white wine sauce, this long-standing favorite erupts with a powerful blend of flavors. The real deal should smolder slightly while cooking, so that the accompanying potatoes, artichokes, and herbs take on a smoky aroma, while the skin on the chicken is crispy and golden. The exact origins of this classic dish remain mysterious, but it’s a definite legacy of the city’s Italian connections.

Local tip: Sample this dish in the iconic Harry Caray’s Italian Steakhouse. It’s known for great cuisine and paying homage to the popular sportscaster.

Steak

Chicago takes pride in its legacy of great steaks, first made famous in the Meatpacking District. Even though the dishes can be simply presented, the taste does all the talking. Served up in traditional steakhouses and swanky fine-dining venues, you’ll find plenty of cuts accompanied by sautéed spinach and a baked potato. Don’t forget a glass of fine red wine.

Garrett’s Popcorn – Chicago Mix (Cheese and Caramel Popcorn)

Hungry customers form long lines outside Garrett’s to chow down on their famous sweet and crunchy CaramelCrisp popcorn (also available with nuts mixed in), as well as melt-in-your-mouth CheeseCorn. They might seem wrong, but they taste so right. But if you want something more traditional, try the classic buttery popcorn – it‘ll still be some of the best you’ve ever had!

Local tip: Garrett’s original downtown shop attracts both locals and visitors as they walk down Michigan Avenue.

Breaded Steak Sandwich

A bread roll filled with fried steak, dipped in marinara sauce, and smothered in melty mozzarella is the foundation of this sturdy sandwich. This hearty snack combines quintessential Chicago ingredients and is served in a sub-style bun with spicy giardiniera relish and hot peppers.

Local tip: Find the roots of this delicious sandwich and head to its birthplace, Ricobene’s Restaurant in the Bridgeport neighborhood.

Chicago Tamales

Wrapped in either a banana leaf or a corn husk, tamales are a delicious little package of masa (cornmeal) filled with spiced meat. It’s a treat waiting to be unwrapped. Top them with anything from grated cheese and sour cream to chunky salsa or fiery guajillo sauce.

Local tip: Keep an eye out for the legendary “Tamale Guy.” Chicagoans swear he’ll turn up when you need him most…after you’ve had a few late at night!

Chicago Italian Beef

The iconic Italian beef sandwich is a meaty and messy meal made up of thin layers of juicy beef piled on an Italian bread roll. Then (if your heart desires) it’s dipped back into the broth and served with either sweet or hot peppers on it.

Local tip: Chicagoans ask for a nice, long dip back into the cooking juices – but if you prefer your sandwich not to be soaking with grease, don’t worry, it’s acceptable to get it “dry.”

Goose Island Beer

Goose Island’s delicious bourbon-aged beers are considered some of the best in the world. Brewed in Chicago and using hops grown in the rich countryside of Northern Idaho, the brewpubs in Chicago have an extensive list of in-house varieties. Signature beers include their IPA, 312 Urban Wheat Ale or the classic Honkers Ale.

Local tip: Take a tour of the Lincoln Park brewery to sample a variety of beers and get the full Goose Island experience.

Chicago-style Hot Dog

Chicago takes its hot dogs very seriously and stands across the city try to outdo each other with the same core ingredients. A Chicago dog is a beef sausage in a poppy-seed bun, and if you get it with “the works,” it’s topped with yellow mustard, bright green relish, onion, celery salt, tomato wedges, sport peppers, and a pickle spear. Don’t even think about asking for ketchup!

Local tip: Head to the Lincoln Park area to track down some of the latest crazes in Chicago dog toppings, including spicy sriracha mayonnaise, duck egg and pineapple.

Maxwell Street Polish

This simple sausage’s popularity hasn’t changed during its 70-year history. Beef and pork-mixed sausages first started to sizzle on the grill at Jim’s Maxwell Street stand in 1943. Placed in a hot dog bun, smothered in sweet onions and drizzled with yellow mustard, the sandwich is accompanied by a pickle and a free portion of fries. The recipe has stayed true to its origins and lines continue to form at Jim’s during lunchtime.

Local tip: Jim’s original Maxwell Street stand has evolved into a shop that you’ll now find on Union Avenue.

Flaming Saganaki

Starting out as a block of tangy Graviera cheese, this dramatic Greek dish is flambéed with brandy and put out with a squeeze of fresh lemon. Diners usually order this as a tasty starter with bread so they can scrape up all the burnt edges.

Local tip: A serving of flaming saganaki is often greeted by diners and waiters shouting “Opa!” as it makes its way to the table.