Chicago Must-Eats: Food in The Windy City

Chicago Must-Eats: Food in The Windy City best restaurants and bars in the Second City

Chicago is a great destination for foodies! But with so many iconic dishes to choose from, it is easy to get overwhelmed. Let us help you plan a trip to the windy city, with our selection of Chicago must-eats. 

Chicago Staples

Chicago Staples iconic foods deep dish pizza, Chicago-style hot dogs, Italian beef sandwiches, and gourmet popcorn

The city is famous for certain foods, and you would be remiss not to try them while you are in town. 

An obvious one is deep dish pizza. The thick bready base stuffed with gooey cheese and topped with a rich tomato sauce is a hearty meal for hungry travelers. This unique style of pizza was first introduced at Pizzeria Uno in 1943, and it is now popular across the city (and the world). Almost casserole-like, the inverted pizza (crust, cheese, toppings, then tomato sauce) has changed the way people think about pizza. Pizzeria Uno is still open if you want to taste deep dish pizza at its source. However, the city has a lot of restaurants that claim to have perfected the dish. Some favorites include Lou Malnati’s Pizzeria, Pequod’s Pizza, Giordano’s, and Pizano’s Pizza & Pasta.

Italian beef is another must-try foodstuff in the windy city. This tasty hot sandwich features thin slices of roast beef soaked in a rich seasoned au jus. The meat is served on French bread and topped with giardiniera – an Italian relish consisting of vegetables (typically bell, olives, carrots, and cauliflower) pickled in vinegar or oil. Most Chicagoans go a step further and dip their entire sandwich in a bowl of au jus. Many Chicago eateries claim to serve the best Italian beef sandwich, but some standouts include Al’s #1 Italian Beef (which has operated since 1938), Johnnie’s Beef, Buona, and Tony’s Italian Beef.

Don’t leave the city without biting into a Chicago-style hot dog. It is an all-beef frankfurter on a poppy seed bun, topped with mustard, relish, chopped raw onions, tomato slices, pickled sport peppers, a dill pickle spear, and a dash of celery salt. Most importantly, a Chicago-style hot dog never has ketchup! This tasty treat is not just for sports fans. You can find it at a variety of street vendors and fast-food restaurants around the city. Some popular hot-dog spots include Gene & Jude’s (which claims to have the best hot dog in the United States), Portillo’s, Redhot Ranch, and Superdawg Drive-In.

Another unmissable Chicago treat is gourmet popcorn. Garrett Popcorn has been popping small batches of corn since 1949. It is famous the world over for its mixture of cheddar and caramel popcorn.

Award-Winning

Award-Winning restaurants and bars such as Michelin-starred eatery Alinea and Au Cheval's top burger in America

Both Bon Appetit and the Food Network have declared that Au Cheval has the top burger in America! We have tasted the fantastic hamburger ourselves and certainly agree it’s a contender. 

In the West Loop neighborhood of Chicago, you step into an unassuming diner-style restaurant (we recommend sitting at the counter to watch the magic happen) and order a cheeseburger. If you order a single, you will be presented with two prime beef patties cooked medium, but the restaurant offers a double cheeseburger with three (yes three!) patties. Each is topped with a slice of Kraft American cheese. The bun is toasted on both sides and dressed with Dijonnaise and house-made pickles. To make your burger even more decadent, we recommend topping it with Au Cheval’s thick-cut peppered bacon and a fried egg. The impressive sandwich arrives with a sharp knife down the middle, to hold all the toppings in place. 

Please note, Au Cheval does not take reservations, but the line tends to move quickly. Trust us, the burger (especially with the peppered bacon) is worth the wait. 

Alinea is a James Beard Foundation Award winner, AAA Five Diamond Award winner, and the restaurant boasts three Michelin stars! The creative kitchen produces whimsical, experimental items that are a feast for the senses as well as the palate. The chef incorporates aromas, music, and theater into the multi-course meal.

One of Alinea’s most famous dishes is its colorful, deconstructed dessert that is spread across the table like a Jackson Pollock painting. Depending on your budget, you can choose from three different experiences at Alinea: the Kitchen Table, The Gallery, and The Salon. They vary in terms of seating arrangement and number of courses, but at a minimum, you should expect to spend $200+ per person. If you love modern food and have the funds to splurge, you can certainly do so in Chicago.

The second city often hosts pop-up bars and restaurants featuring award-winning brands from around the world. For example, during our upcoming trip we will be heading to the Four Seasons Hotel Chicago because it has partnered with Mexico City’s Handshake Speakeasy. It is #1 on The World’s 50 Best Bars list. If you have read our article Raise A Glass: Best Bars In Mexico City, you will know that we have sampled Handshake’s magical concoctions and highly recommend the bar. The Chicago pop-up cocktail experience is held at the Four Seasons’ intimate Mile High Cocktail Club (a suite that has been converted into a speakeasy) and features a welcome glass of champagne and two specialty cocktails. The event runs from November 14, 2024 to March 1, 2025, so if you are lucky enough to travel during that time…cheers! If not, here’s hoping there is a similar food or drink event when you visit. 

Personal Favorites

Personal Favorites dishes in Chicago such as stone crab claws, prime rib and cocktails at Lazy Bird.

Chicago has restaurants that serve some of our favorite types of food. It is a foodie mecca where you can find delicacies from across America. 

A must-eat when we visit the USA is prime rib. It is a dish that is hard to find in other countries, and something we always find satisfying. The windy city has some fantastic steakhouses that serve prime rib, including Chicago Chop House, Boeufhaus, Carson’s Ribs Prime Steaks & Famous Barbecue Chicago, and Gibsons Bar & Steakhouse. By the way, Gibsons also has a mouth-watering macadamia turtle pie for dessert.  

Despite being landlocked, Chicago has some delicious seafood. In fact, our favorite Miami restaurant Joe’s Seafood, Prime Steak & Stone Crab has a branch there. Joe’s carries fresh stone crab claws in various sizes, and its staff crack the shells for you. The crab is paired with a tasty mustard cream dipping sauce. A meal at Joe’s isn’t complete without a slice of tangy key lime pie. If you are looking for a taste of Florida in Illinois we highly recommend it!

If you are in search of the perfect tipple, head to Lazy Bird. Hidden in the basement of The Hoxton hotel is a speakeasy with wonderful cocktails and a hip vibe. The extensive menu resembles a periodic table — it is impossible to order just one cocktail. You can stick to a classic such as a negroni, whisky sour, old fashioned, or French 75. Alternatively, you can opt for a unique Lazy Bird creation like “5 pm in Chicago,” “Jazz Lingo,” or “Emerald City.” The trick is to look on the right side of the menu to find seasonal cocktails and bartender specials. 

We have not even scratched the surface of Chicago’s food and drink scene. However, we hope we have sparked your interest in the city, so you plan a trip there soon! If you have visited and have some personal favorite eateries, please comment below.

If you are interested in content aimed at foodies, please check out our articles 27 Dishes: Popular Food In Each EU Country, Best Places for Coffee Connoisseurs, and How To Eat Your Way Through Paris

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