5 Must Eats in Chicago

A hot, buttery scent drifting through the air in the Windy City is a surefire sign that you’re within walking distance of a Garrett’s Popcorn Shop. Eagerly devoured by hungry Chicagoans since 1949, the impossible-to-resist snack is hot air-popped and mixed with unique flavors that range from sweet caramel to savory cheese.  

The first Garrett’s Popcorn Shop opened in the Loop, in Chicago’s busy downtown, with a crispy caramel popcorn that soon had customers queuing out the door. The tangy CheeseCorn followed, and by the 1970s it was common for customers to mix the 2, creating what is now the famous “Garrett Mix.” There are a multitude of branches in Chicago, including several on the fabled Magnificent Mile.

Think of the Chicago food scene, and it’s impossible not to think of deep-dish pizza. These deliciously cheesy, heavily laden pizzas are as synonymous with the Windy City as the Chicago Flag. Supposedly, it was invented in 1943 at Pizzeria Uno, a nationwide chain with an enduringly popular branch in Chicago today, and the distinctive pizzas are notable for their buttery, pie-style crust that encases layers of cheese, fillings, and rich tomato sauce.

It’s worth taking a walk around the Windy City to build up an appetite for this deep-dish deliciousness, which can be savored at spots across the city, including the famous Uno, and other renowned spots like Pequod’s, Lou Malnati’s, and The Art of Pizza.

If you're looking for a naturally gluten-free sandwich that packs a real flavor punch, try the jibarito. As quintessentially Chicagoan as deep-dish pizza and rib-eye steak, this supremely satisfying sandwich reflects the enduring influence of Puerto Rican flavors on Chicago’s culinary scene.

This true modern classic exploded onto the food scene as recently as the 1990s and sees thin-cut steak, salad, cheese, and a hit of garlic oil sandwiched between slices of twice-fried plantain. It’s a less carb-heavy version of the traditional sandwich, although the richness of the filling means one jibarito is enough to satisfy the heartiest appetite. Top places to try the dish include Jibaritos y Mas, Jibarito Time, and there’s a vegetarian version, which features seitan, at Ground Control.

Carnivores, prepare for foodie heaven when you visit Chicago, because this is a city that takes its steaks seriously. And it’s not without good reason that Chicago-style steak has found favor with beef lovers across the United States and beyond.

Deliciously charred on the outside and cooked to your preference inside, Chicago-style steak is most commonly made with bone-in ribeye steak although other lean cuts can be used. The steak is then simply seasoned and cooked over a high heat. The quality of the meat is paramount to the success of this in-demand dish, so be sure to try it at a well-established steakhouse such as Gibsons Bar & Steakhouse, where it makes the perfect partner to a classic martini.

A huge hit with children and grownups alike, Chicago’s Original Rainbow Cone ice creams have been thrilling visitors since they were first sold from a humble shack in 1926. The winning formula combines 5 distinct but equally delicious flavors: chocolate, strawberry, orange sherbet, pistachio, and “Palmer House,” which is vanilla with nuts and cherries. The surprisingly tasty confection is then piled precariously onto a traditional cone.

There are now multiple branches of Original Rainbow Cone across Chicago, but for the ultimate ice cream pilgrimage it’s best to visit the branch where it all began, South Western Avenue. If you need further proof that Chicago is a destination for ice cream lovers, check out the city’s famous Museum of Ice Cream.