Chowing Down in the Windy City: A Food Lover’s Tour of Chicago

Chicago is a city that is renowned for its architecture, culture, and sports. However, the Windy City is also a foodie’s paradise, with an eclectic mix of cuisines that range from deep-dish pizza to haute cuisine. If you’re a food lover visiting Chicago, you’ll be spoiled for choice. In this article, we’ll take you on a tour of some of the best places to chow down in the Windy City. 

Deep Dish Pizza 

When it comes to Chicago cuisine, deep-dish pizza is a must-try. This hearty pie is characterized by its thick crust, ample cheese, and chunky tomato sauce. There are many places to indulge in this local specialty, but one of the most famous is Lou Malnati’s Pizzeria

With locations throughout the city, Lou Malnati’s has been serving deep-dish pizza since 1971. The crust is flaky and buttery, the cheese is gooey and plentiful, and the sauce is tangy and robust. Be sure to try the “Malnati Chicago Classic,” which is topped with Lou’s exclusive sausage blend, extra cheese, and vine-ripened tomato sauce. 

Hot Dogs 

Chicago-style hot dogs are a beloved local specialty that can be found at street carts and restaurants throughout the city. The classic Chicago-style hot dog is a beef frankfurter topped with yellow mustard, chopped onions, sweet pickle relish, tomato wedges, pickled sport peppers, and a sprinkle of celery salt. 

One of the most famous purveyors of Chicago-style hot dogs is Portillo’s, which has locations throughout the city and suburbs. In addition to hot dogs, Portillo’s also offers Italian beef sandwiches, char-broiled burgers, and decadent chocolate cake. 

Craft Beer 

Chicago’s craft beer scene has exploded in recent years, with dozens of microbreweries and brewpubs popping up throughout the city. One of the best places to sample local brews is Revolution Brewing, which has two locations in Chicago. 

The brewery’s flagship beer is the Anti-Hero IPA, a hoppy and refreshing brew that has won numerous awards. The brewpubs also serve up delicious food, with a menu that features pub classics such as burgers, sandwiches, and loaded fries. 

Italian Beef Sandwiches 

Another Chicago specialty is the Italian beef sandwich, which is made with thinly sliced roast beef, Italian seasoning, and au jus on a crusty roll. One of the best places to try this local favorite is Al’s Beef, which has been serving up Italian beef sandwiches since 1938. 

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The beef is cooked to perfection and sliced paper-thin, then piled high on a fresh-baked roll. Be sure to ask for the sandwich “dipped” or “wet” for a more flavorful experience. Al’s Beef also offers hot dogs, burgers, and sausage sandwiches.


For those with a sweet tooth, Chicago has plenty of options to satisfy your cravings. One of the most popular spots for donuts is Do-Rite Donuts, which has locations throughout the city. Their donuts are made from scratch daily, with a variety of creative flavors such as maple bacon, key lime pie, and Nutella. Do-Rite Donuts also offers gluten-free and vegan options, so there’s something for everyone. 


If you’re in the mood for a hearty steak dinner, Chicago has some of the best steakhouses in the country. One of the most iconic is Gibsons Bar & Steakhouse, which has been serving up prime cuts of meat since 1989. 

The menu features everything from filet mignon to bone-in ribeye, all cooked to perfection and served with classic sides such as creamed spinach and garlic mashed potatoes. In addition to steak, Gibsons also offers seafood and pasta dishes, as well as an extensive wine and cocktail list. 

Cocktails and Spirits in Chicago 

Chicago is not just a foodie’s paradise, it’s also a cocktail lover’s dream destination. The city has a thriving cocktail scene, with numerous bars and lounges serving up creative and innovative drinks. Whether you prefer classic cocktails or modern twists, there’s a cocktail bar in Chicago that will satisfy your cravings. 

The Aviary 

Among the shortlist of the best cocktail bars in downtown Chicago is The Aviary, which is located in the West Loop neighborhood. This award-winning bar is known for its inventive drinks that push the boundaries of traditional mixology. The Aviary’s cocktail menu features unique creations such as the “In the Rocks,” which is a drink served inside a hollow ice sphere, and the “Science A.F.,” which is a cocktail made with gin, citrus, and a science-inspired garnish. 

The Violet Hour 

Another iconic cocktail bar in Chicago is The Violet Hour, which is located in Wicker Park. This speakeasy-style bar is known for its intimate atmosphere, classic cocktails, and extensive spirit selection. The Violet Hour’s cocktail menu features drinks such as the “Old Fashioned,” “Manhattan,” and “Sazerac,” as well as creative seasonal offerings. 

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Lost Lake 

For those who love tropical cocktails, Lost Lake is a must-visit destination. Located in Logan Square, this tiki-themed bar is known for its exotic drinks that transport you to a tropical paradise. The menu features drinks such as the “Jungle Bird,” “Piña Colada,” and “Zombie,” all served in elaborate tiki mugs and garnished with tropical fruits and umbrellas. 

Three Dots and a Dash 

Another tiki-themed bar in Chicago is Three Dots and a Dash, located in River North. This Polynesian-inspired bar is known for its creative drinks, such as the “Painkiller” and “Missionary’s Downfall,” which are served in tiki mugs and garnished with tropical flowers and fruits. The atmosphere is also impressive, with dim lighting and a tropical decor that transports you to a faraway island. 

The Barrelhouse Flat 

If you prefer classic cocktails with a modern twist, The Barrelhouse Flat is the place to be. Located in Lincoln Park, this cocktail bar offers a range of drinks, from classic cocktails such as the “Negroni” and “Martini” to unique creations like the “Smokey Robinson,” which is made with scotch, mezcal, and lapsang souchong tea.

Mexican Cuisine 

Chicago is home to a vibrant Mexican community, and the city is known for its delicious Mexican cuisine. One of the best places to indulge in authentic Mexican flavors is La Chaparrita, located in the Little Village neighborhood. 

The menu features traditional dishes such as tacos, tamales, and chiles rellenos, as well as more exotic offerings such as cow’s tongue and goat stew. Be sure to try the homemade salsas and guacamole, which are the perfect accompaniments to any dish. 

Something for Everyone

Chicago’s food scene is diverse and delicious, with options to satisfy every palate. From deep-dish pizza to craft beer to authentic Mexican cuisine, there’s something for everyone in the Windy City. So, the next time you’re visiting Chicago, be sure to come hungry and chow down on some of the city’s best culinary delights.