5 Things You Must Eat When in Chicago

Jul 30, 2024 at 2:25 pm

Chicago has more to offer than baseball season and record-breaking winter weather. The Windy City brims with life across its lively streets of commingling cultures, its iconic architecture and its outrageously delicious food. So if you’re a foodie in need of a culinary adventure in a walkable city, you’ve come to the right place.

We’ve curated a list of five iconic Chicago eats that will turn your visit into a flavor-packed extravaganza. We’ve got you covered from light snacks to a full feast!

  1. Relish in a Chicago-Style Hot Dog

Everyone knows there’s no city more passionate about hot dogs than Chicago, and Chicago dogs are just built different. First of all, skip the ketchup. Instead, you get a parade of mustard, onions, relish, tomato slices, pickles and a sprinkle of celery salt topped on a beef frankfurter resting in a poppy seed bun. That’s how Chicago spices up its most famous street eat.

Chicagoans refer to this iconic dish as “dragging the dog through the garden." | (Photo/Portillo’s)

For an authentic taste, head to Portillo’s, where hot dogs are served with a side of hots and a friendly face. Or, if you like your meal served with some of that unique Chicago attitude, visit The Wiener's Circle.

  1. Deep-Dish Pizza — That’s Basically a Pie

With a thick, buttery crust that cradles layers of gooey cheese and luscious tomato sauce, this pizza is practically a meal within a meal. Just one slice of this savory pie goes a long way.

Deep cheesy tomato pizza dish roasting on an open fire | (Photo/Lou Malnati’s)

You might wonder if it is a tomato cheese pie or just a big pizza with the toppings flipped upside down. One thing’s for sure: Deep dish pizza is best enjoyed with a big group of friends and family.

Pizza in Chicago is a hotly debated topic. Many would say Lou Malnati’s is the reigning champion of this cheesy concoction. But if you're a fan of crispy, caramelized edges, Pequod’s Pizza is a must-try.

  1. Italian Beef: A Sandwich Worthy of a Drama Series

The Italian beef sandwich is a flavorful mess crafted by the city's Italian immigrant community in the early 1900s that today has become a Chicago staple.

Stuffed with tender, seasoned beef and drenched in a savory, spicy jus, it’s a sandwich that requires a bib, gloves, and possibly a mop.

Al’s beef has won over 150 culinary & critic awards as Chicago’s favorite sandwich for over 83 years | (Photo/Al’s Beef)

You know a sandwich is good when it comes with its own lore. Al’s Italian Beef, named after the founder's son, is reported to be the birthplace of this iconic sandwich. For an authentic taste of Chicago's beef heritage, visit Mr. Beef on Orleans. This establishment, featured in the acclaimed TV series The Bear, boasts a casual dive-bar atmosphere and serves beef that is nothing short of extraordinary.

  1. Kettle Corn: Popcorn’s Fancy Cousin

We’re not talking about just any regular popcorn here. On the spotlight is kettle popcorn popped to perfection and mouth watering flavors, from plain and butter classics to the innovative Spicy Cheese Corn and Caramel Crisp recipes that come with four options — pecan, macadamia, cashew and almond.

Garrett Popcorn cooks small batches throughout each day to ensure the freshness in each bucket | (Photo/Garret Popcorn)

But the crown jewel among them is an indulging blend of cheddar cheese and caramel—a sweet and savory duo that’s poppin’ with joy. Garrett Popcorn Shops are your go-to for this gourmet popcorn extravaganza.

  1. Rainbow Cone: Ice Cream So Good They Froze It In Time

This last treat is so photogenic that haters will say it’s Photoshop. Rainbow Cone is a literal slice of history. Five flavors pile high in slices, not scoops, perched atop a sugar cone.

The shop continues to stack the same five flavors in the same order, slicing and not scooping them into a cup or cone | (Photo/Original Rainbow Cone)

A Chicago staple since 1926, a Rainbow Cone stacks up chocolate, strawberry, Palmer House (a vanilla concoction with cherries and walnuts), pistachio and orange sherbet in one epic tower of sweetness. It’s truly a dessert worthy of the Chicago skyline.

For the ultimate Rainbow Cone experience, visit the Original Rainbow Cone in Beverly or its Navy Pier location.

So the next time you hit up the Midwest for a gastronomy adventure, remember that Chicago takes its food seriously as it does its sports. Dive into this culinary tour and leave with your stomach satisfied in this Windy City that will take your food cravings away.