Chicago, Illinois Must-Eats: Classic Bites and Can’t-Miss Restaurants

Pizza, hot dogs and Italian beef: You haven’t eaten in Chicago if you haven’t tried them. Chicago-style pizzas include several indulgent varieties: deep-dish (meaning deep-molded crusts layered with cheese, toppings and sauce), stuffed (similar to deep-dish but covered with a second crust, then topped with sauce) and thin-crust (featuring a crunchy crust cut into squares). Try Lou Malnati’s, where the buttery crust and meticulously crafted ingredients make it a Chicago institution.

When it comes to the classic Chicago dog, look for tomato slices, relish, onions, mustard, a pickle spear, sport peppers and celery salt on a poppy-seed bun – no ketchup! Get the real deal at Portillo’s. The line is long but moves quickly. Finally, try an Italian beef sandwich at Al’s Italian Beef, the go-to for thinly sliced beef on an Italian roll served with either sweet peppers or spicy giardiniera (pickled vegetables), then dipped in pan juices. Grab extra napkins for this one.

The Midwest is a hub for cattle ranching, influencing Chicago’s long tradition of steakhouses. Dry-aged beef is the standard, with Gibsons Bar & Steakhouse at the forefront. Known for huge cuts of prime angus beef and classy cocktails, Gibsons is the only restaurant in the USA with its own USDA Certified Angus Beef program. Needless to say, it’s a must-try. To sample more of the city’s finest steaks, hop on the Chicago Steakhouse Tours bus to try three quintessential Chicago steakhouses. Part history lesson, part culinary tour, Chicago Steakhouse Tours is the tastiest way to learn about the city’s affinity for beef.

Chicagoans love a good ribeye, but there’s plenty of fresh and leafy cuisine to be found, too. Cindy’s Rooftop at the Chicago Athletic Association Hotel features ultra-fresh, seasonal ingredients along with an innovative menu of chic cocktails. It doesn’t hurt that the open-air terrace boasts one of the most spectacular views in the city, overlooking Millennium Park, the Art Institute of Chicago and Lake Michigan.

Chicago serves as Illinois' and the Midwest’s major transportation hub, with two international airports offering worldwide service. Fly in to O’Hare (ORD) or Midway (MDW); both airports offer multiple transportation options into the city, including trains, shuttles and rental cars.