Generous, hunger-vanquishing favourites to savour in the Windy City

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From sizzling sandwiches to cavernous pizza pies – each of these 12 Chicago Town treats is a classic.

All the best bits of a pizza, quadrupled

All the best bits of a pizza quadrupled

Deep dish pizza

More like a pie than a pizza, it takes 45 minutes to bake alone. Made in a deep pan to form a high-edged flaky crust, popular ‘toppings’ like sausage, cheese and spinach are layered up to the brim. Chunky tomato sauce is always added last to enable a longer cooking time without burning the other ingredients. So it’s an upside-down pizza too!

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

A traditional sandwich with a surprising Puerto Rican twist

A traditional sandwich with a surprising Puerto Rican twist

Jibarito (Fried Plantain Sandwich)

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

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

An Italian-American chicken dish smoking with flavour

An Italian-American chicken dish smoking with flavour.

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Chicken Vesuvio

Sizzling in a white wine sauce, this long-standing favourite erupts with a powerful blend of flavours. The real deal should smoulder 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.

Legendary steak with a long history

Legendary steak with a long history

Steak

Chicago takes pride in its legacy of great steaks, first savoured in the Meatpacking District. Though the dishes may be simply presented, the taste does all the talking. Accompanied by sautéed spinach and a baked potato, a variety of cuts are served up in traditional steakhouses and sumptuous fine-dining venues — along with a glass of fine red wine.

A savoury-sweet snack offering the best of both worlds

A savoury-sweet snack offering the best of both worlds

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

Hungry customers form a long queue outside Garrett’s to feast upon their famous combination of sweet and crunchy CaramelCrisp and melt-in-the-mouth CheeseCorn. It’s an unusual blend that goes down a treat but if you fancy something a little more traditional, sample some classic buttery corn, or one of the shop’s many nutty combinations.

Local tip: Garrett’s downtown shop acts as its flagship store with locals and visitors stopping by as they take a walk by Lake Michigan’s shores.

A sandwich of generous proportions celebrating Chicago’s Southside

A sandwich of generous proportions celebrating Chicago’s Southside

Breaded steak sandwich

A slither of breaded and fried steak is dipped in marinara sauce and smothered in stringy mozzarella to make the foundations of this sturdy sandwich. This hearty snack combines quintessential Chicago ingredients, served in a sub-style bun and complemented by a fiery dash of giardiniera relish and hot peppers.

Local tip: Get back to the roots of this tasty treat in its birthplace, Ricobene’s Restaurant in the Bridgeport district.

A spicy Mesoamerican treat jam-packed with flavour

A spicy Mesoamerican treat jam-packed with flavour

Chicago tamales

A little parcel of spiced ground meat filling wrapped in masa, or cornmeal, tamales should always be served in a banana leaf or corn husk. Once unwrapped, they can be garnished with anything from mild 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 that he’ll turn up in bars late at night when revellers are at their hungriest!

A unique take on a beef sandwich

A unique take on a beef sandwich

Chicago Italian beef

The beloved Italian beef sandwich is hearty if slightly messy, affair. Thin layers of roast beef are doused in the meat’s cooking juices before being placed in an Italian bread roll, then dipped again. You can opt for sweet or hot peppers to be put on top before a dash of tangy giardiniera relish is added.

Local tip: Locals tend to favour the sandwich dipped not once but twice — but if you prefer your sandwich not to be dipped, ask for it “dry” when you order.

Home-grown beer with a European flavour

Home-grown beer with a European flavour

Goose Island Beer

Goose Island’s tasty bourbon-aged blends were inspired by craft beers first made popular across the pond. Brewed in Chicago from hops grown in the lush landscape of Northern Idaho, the beer has a fruity feel without being too sweet. Signature fusions include their tasty IPA, Saison Ale or Pils.

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

Upgraded hot dogs with a medley of toppings

Upgraded hot dogs with a medley of toppings

Chicago style hot dog

Chicago takes its hot dogs very seriously and eateries across the city outdo one another with their colourful concoctions of garnishes. The general theory is the more toppings, the better. The result is a beef sausage encased in a poppy-seed bun and “dragged through the garden”, as the local saying goes – topped with yellow mustard, bright green relish, onion, celery salt, tomato wedges, a chilli pepper and a pickle spear.

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.

A sausage sandwich that goes way back

A sausage sandwich that goes way back

Maxwell Street Polish

This simple snack’s popularity hasn’t faltered during its 70-year history. Polish beef and pork-mix 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 French fries. The recipe has stayed true to its origins and queues continue to format Jim’s every lunchtime.

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

A flaming tasty slice of savoury Greektown goodness

A flaming tasty slice of savoury Greektown goodness

Flaming saganaki

Starting out as a block of sweet Graviera cheese, this Greek dish is dramatically flambéed with brandy and extinguished with a squeeze of lemon juice. Diners order this as a tasty starter with bread to soak up the creamy mix.

Local tip: A serving of flaming saganaki is often greeted by diners and waiters with an exclamation of “Opa!” as it arrives at the table.

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