Chicago is an ideal city to try new foods and drinks. We’ve gathered a few of the most unusual and fun places to eat in the Windy City.

If you need help deciding which one to visit, consider a food tour. You’ll get to sample dishes from several establishments, learn more about Chicago’s rich (and tasty) heritage, and have a memorable experience with your group.

Ultimate Chicago Food Tour: West Loop Neighborhood

The West Loop is a food lover’s paradise, from Chicago classics to modern international cuisine. Unlike other foodie neighborhoods, the West Loop caters to every palette—from comfort food and burgers to fine dining and everything in between. And it goes beyond restaurants: there are remarkable food halls where you can indulge in your favorite treats from around the world; craft cocktail bars that serve up delicious libations inspired by regional flavors; and even gourmet popcorn shops for those with a sweet tooth.

 

Chicago deep-dish pizza

 

West Loop Pizza Walk

The West Loop is a thriving foodie haven. It’s home to the best of Chicago’s pizza parlors—and this tour takes you on a walking tour to sample them all. Learn about the city’s ten styles of pizza and its history from a dough-centered guide. You’ll also get caught up on the history of the West Loop and some of its colorful characters.

 

Alinea

Alinea is a Michelin-starred restaurant that serves molecular gastronomy and experimental cuisine–which means they use cutting-edge scientific techniques to improve traditional cooking methods. It’s a popular destination for locals and tourists alike. Alinea also offers cooking classes where you can learn how to recreate their signature dishes at home.

 

Superdawg Drive-In

Superdawg Drive-In is a classic for Chicagoans. It’s been around since 1948, and to this day, it’s still packed with people who come to eat and hang out. The hot dogs are delicious, the burgers are good, and the shakes are amazing.

A beer tap with a beer glass being filled

Kaiser Tiger

If you love German food and beer, Kaiser Tiger is the place for you. This offbeat restaurant serves traditional fare (schnitzel, sauerbraten, and sauerkraut) in a casual, festive setting with more than 100 varieties of beer on tap. The space is extensive—with a capacity of 250—and there’s a small craft cocktail list if that’s more your thing.

Kaiser Tiger opened in 1986 as a bar with a few tables near Chicago’s Lincoln Park neighborhood. Today it has three locations: Lincoln Park, Old Town, and River North. All three serve the same menu and have similar decor. Still, each has unique features, like outdoor seating at the River North location.

 

Kit Kat Lounge & Supper Club

Kit Kat Lounge & Supper Club is a restaurant and bar with an upstairs speakeasy.

The Kit Kat Lounge & Supper Club has been around since 1934 when it was known as the Kegel Tap Room. The bar closed during Prohibition and reopened after the law was repealed in 1933—but this time as a speakeasy.

 

SafeHouse Chicago

SafeHouse Chicago is a unique dining experience housed in the basement of The Pump Room, a bar that’s been around since Prohibition. Settle into a booth and order some drinks from the speakeasy-style bar. Their cocktails are creative, so it’s hard to choose just one.

The food here is equally as remarkable as their drinks, and the kitchen delivers it quickly. Get started with their signature Hoisin Duck Tacos, Pastrami Sandwich, or Sweet Potato Fries. Then wash it down with an Old Fashioned cocktail made with house-made bitters and citrus zest (or whatever else you’re feeling).

Closeup of the Chicago Theatre sign

 

Carnivale

Carnivale is a Brazilian steakhouse on Montrose Avenue that has everything you desire in a restaurant: great food, excellent service, and a fabulous atmosphere.

The restaurant’s menu offers all kinds of meat cooked to perfection by their expert chefs. Carnivale is also known for its delicious caipirinhas—a potent drink made with cachaça (Brazilian rum) mixed with fruit juice.

 

The Wiener’s Circle

The Wiener’s Circle, located in Chicago’s Ukrainian Village neighborhood, is a hot dog joint that has been around for decades that’s popular for its Chicago-style hot dogs. It has a relaxed and casual atmosphere where you order food at a counter and then find a seat inside or outside. If you go on the weekend, expect to share tables with other customers who are just as enthusiastic about their dogs as you are.

If you want a different experience than just eating one type of hot dog, The Wiener’s Circle also serves up vegetarian options, such as veggie dogs and fries. There are also several beer choices available at this restaurant if you want something other than soda with your meal.