Where to Eat

The Best Bites In Chi-Town: Savoring Chicago’s Street Food Scene

Eat like a local when you’re in the Windy City

The Vacationeer
Stunning aerial image, Chicago skyline, clear blue skies, Lake Michigan shoreline, Illinois.

There’s a long list of reasons to love Chicago — from epic sports teams and sky-high shopping experiences to miles of waterways and architectural wonders. But the Windy City is also in a league of its own when it comes to iconic street foods. Famous for Italian beef sandwiches, deep-dish pizzas and fully loaded hot dogs (sans ketchup), Chi-town is a solid choice for foodies with an appetite for stand-out, budget-friendly street eats.

So, as you start to plan your trip and set the stage for adventure at Chicago Magnificent Mile, a Hilton Grand Vacations Club, remember to dig in and enjoy these must-try snacks and signature dishes during your stay.

The Chicago Dog: A Second City Staple

The Chicago-style hot dog has a storied past with working-class roots. It was created out of necessity during the Great Depression as an affordable option for penny-pinching families. To make the meal more nutritious, street-cart vendors added vegetables like tomatoes, peppers and onions. Today, a fully loaded Chicago dog is a beloved culinary creation with a signature aesthetic. It’s been described as a frankfurter with a salad on top.

Chicago-style hot dog, street food.    

For some, it’s a classic snack. For others, it’s a full meal — especially in Chicago. That’s because a true Chicago dog has a specific set of ingredients:

  • An all-beef hot dog
  • A steamed, never toasted, poppy seed bun
  • Yellow mustard
  • Bright green relish
  • Chopped white onions
  • Tomato slices
  • Spicy sport peppers
  • A dill pickle spear (laid parallel to the dog)
  • A dash of celery salt
  • And most importantly: No ketchup.

You can find this famous creation in stands dotted across the city. Here are three popular spots:

Gene & Jude’s

This unassuming, standing-room-only hot dog stand is a Chicago-area institution that’s been serving up the classics since 1946. Gene & Jude’s is known for its masterfully simple menu and well-known rules — “No seats. No ketchup. No pretense. No nonsense.” The only extra flare they bring to the table is the sprinkling of hand-cut fries they add to the top of each hot dog.

Insider tip: It’s a cash-only stand.

Jimmy’s Red Hots

Known for its old-school charm, Jimmy’s Red Hots has been delighting locals and visitors with no-frills counter service and Chicago-style dogs since 1954.

Insider tip: Jimmy’s is open until 1 a.m. every day, and they are strong supporters of the “no ketchup” rule. They don’t even offer packets for your fries.


When it comes to crave-worthy hot dogs, Portillo’s continues to reign supreme in the Second City. There’s a reason this Chicago born-and-based stand (once known as The Dog House) has grown to more than 70 locations across the United States.

The Italian Beef Sandwich: Seasoned Goodness

Like the Chicago-style dog, the Italian beef sandwich has humble, depression-era beginnings. Created in the kitchens of immigrants looking to stretch a serving of meat, this savory sandwich is more than just meat and bread.

Italian roast beef sandwich, Chicago street food.    

The classic dish calls for a few key ingredients. The heart of the sandwich is its thinly sliced and seasoned roasted beef. The veggies come next, as the meat is strewn with optional add-ons such as sweet peppers and giardiniera — a spicy, Italian-style relish made of pickled vegetables.

Then it’s all served on fresh-baked French bread, which you can dunk, dip or sprinkle with the beef stock from the roasting process (a.k.a. the jus, juice or gravy).

Consider stopping by these well-known spots for an authentic Italian beef experience:

Johnnie’s Beef

You’ll find this family-owned gem just outside of the city in Elmwood Park. Johnnie’s Beef is a small, no-frills, cash-only spot that’s been serving Italian beef sandwiches for more than 60 years. Their classic recipes have carried on through generations and continue to beckon loyal customers and visitors alike.

Al’s Beef

The original location of Al’s Beef set up shop in 1938 and claims to have invented the iconic sandwich. You can order nearly any version here, too. Get it dry (a splash of gravy) or dry with gravy on the side. Enjoy it dipped (loaded with gravy) or order it wet (extra gravy).

Chicago-Style Popcorn: Handcrafted Happiness

Let’s start with a fun fact: Popcorn is the official snack food of Illinois. And Chicago takes it to a whole new level. The Windy City put its own spin on the beloved snack with a signature mix that blends sweet and salty in perfect harmony:

  • Caramel corn. Fresh popcorn coated in a sweet and buttery caramel glaze with a delightfully crunchy and sticky texture.
  • Cheese popcorn. Popcorn covered in a savory cheese-flavored seasoning with a tangy flavor, cheesy aroma and natural crunch.
Flat lay image, Chicago street food, cheese and caramel popcorn.    

This classic mix has become a big part of the Chicago’s culinary character, and you can find it sold by the bucket throughout the city. But there’s one brand that’s been delighting fans for generations: Add Garrett Popcorn to the list of street eats you want to sample during your visit.

Garrett Popcorn

Garrett has been handcrafting popcorn in Chicago for over 70 years. You’ll find multiple locations across the city, many with lines out the door. Their most famous flavor is The Garrett Mix, a blend of sweet CaramelCrisp and savory CheeseCorn. And every morning, they cook small batches of their secret family recipe using old-fashioned copper kettles.

Deep-Dish Pizza: Stuffed With Flavor

Any way you slice it, Chicago is a deep-dish pizza town. And you’ll need a fork and knife to dig in. Because deep-dish isn’t made to fold like an NYC-style slice. It’s a thick, slow-cooked, cheesy and sauce-covered dish that you’ll want to sit down to experience.

Here’s what sets a deep-dish pie apart from the thin-crust variety:

  • It’s baked in a high-sided metal pan.
  • The two- to four-inch-tall crust is thick, buttery and almost biscuit-like.
  • Toppings are added in reverse order (for an upside-down approach) — with cheese on the bottom, then meat and veggies on top of the cheese.
  • Finally, everything is covered with fresh sauce on top.

It’s the kind of deliciousness that makes you want to mark your calendar for National Deep Dish Pizza Day, which is celebrated on April 5th every year. So, when you’re ready to try this culinary masterpiece, check out these two popular pizzerias:

Lou Malnati’s Pizzeria

With over 60 locations, Lou Malnati’s is one of the Windy City’s most recognizable pizza brands. Every pie is handmade from scratch, and the secret family recipe for their trademarked butter crust has been passed down for generations.

Bartoli’s Pizzeria

When it comes to deep-dish, Bartoli’s stands out with multiple awards. This family-run gem is all about using fresh, high-quality ingredients and making everything from scratch. Consider ordering Nonna Bartoli’s special spinach and cheese deep-dish for a tasty spin on a classic.

Read “Chi-Town Foodies Reveal Chicago's Hidden Gems” for more delicious ideas on where to eat in the Windy City.

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The Vacationeer

The Vacationeer is a collective of Hilton Grand Vacations storytellers whose goal is to inspire travelers to go further. We're always on the lookout for new destinations to explore, useful travel tips, and unique ideas to help you plan the most memorable vacations possible.

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