Finding great places to eat is never a problem during a Chicago vacation; the problem is how to fit them all in! If it’s your first trip to this destination, you’ll want to make sure to sample its iconic eats: Chicago-style hot dogs, deep-dish pizza and the Italian beef sandwich. Indulge in dinner at one of the city’s classic steakhouses, and when you’re ready for a snack, crunch on a unique popcorn blend or cool off with a rainbow of ice cream flavors.
Chicago-Style Hot Dogs
When you order a hot dog in Chicago, be prepared for something a little different than your average ballpark frank. The Chicago-style dog is typically an all-beef frankfurter on a steamed poppy seed bun, topped with mustard—never ketchup— and “dragged through the garden,” meaning it gets additional toppings including chopped onions, sweet pickle relish, sliced tomatoes, sport peppers and celery salt. Portillo’s (100 W. Ontario St. and other locations) serves up a great classic version with a juicy Vienna Beef dog. Got a car? Head to Superdawg Drive-In (6363 N. Milwaukee Ave.). This drive-in restaurant has been serving up its version of the Chicago-style dog, sans tomatoes, since 1948.
Deep-Dish Pizza
As with the hot dog, when in Chicago, get ready for something a little different when it comes to pizza. For example, where’s the cheese? Don’t worry, there’s plenty of gooey, stretchy melted mozzarella. It’s just under the sauce. The ingredients in a Chicago deep-dish pizza are assembled in reverse for a couple of reasons. The thick pie requires a longer baking time than thinner-crust pizza, so the cheese would burn if it were on top. Also, placing the cheese under the sauce keeps it from soaking into the crust and making it soggy. The result? A double helping of delicious pizza flavors atop a bowl-like crust that is crisp and sometimes buttery on the outside. Giordano’s Famous Stuffed Pizza (223 W. Jackson Blvd.) offers an especially unique version, with a layer of crust beneath the cheese that hides a middle layer of filling. For a truly classic deep-dish pizza with a flaky, buttery crust, try Lou Malnati’s Pizzeria. (There are multiple locations, but chances are you’ll be near the 805 S. State St. store during your trip as it’s near Grant Park.)
Italian Beef
You’ll find various versions of the origin of this Chicago sandwich staple, but the end result is the same: spicy roast beef sliced thin, soaked in its own pan juices and served on an open Italian roll. Order it “sweet,” with roasted or grilled sweet peppers, or “hot,” with a spicy pickled vegetable mixture known as giardiniera. Finally, choose “dry” or “dipped” in beef pan juices. You can’t go wrong with Al’s No. 1 Italian Beef (1079 W. Taylor St.), which has been serving up Italian beef sandwiches since 1938. Portillo’s (100 W. Ontario St.), home of the excellent Chicago-style hot dog mentioned above, also gets raves for its Italian beef.
Snacks
When the urge to snack strikes, head to one of the locations of Garrett Popcorn Shops (the 173 N. Michigan Ave. store is near the Grant Park attractions). This iconic shop has been offering varieties of freshly made gourmet popcorn since 1949. Year-round varieties include plain, buttery and nut-and-caramel mixes, but the most popular flavor is the sweet-and-salty Garrett Mix, a blend of caramel and cheese flavors. If touring this walkable city on a hot summer day has you screaming for ice cream, cool off at Original Rainbow Cone (9233 S. Western Ave.) with the Original: a waffle cone topped with layers of flavors including chocolate, strawberry, Palmer House (vanilla with cherries and walnuts), pistachio and orange sherbet.
Steak
Chicago has a history as the heart of the meatpacking industry, and as you can tell by its sandwich specialties, it’s still a beefy kind of town. But the best the city offers is not all served on a bun. Some of the country’s greatest steakhouses can be found here, so make sure you have one on your list of local restaurants to visit during your vacation. Surround yourself with Chicago's past as you enjoy a wet- or dry-aged Prime steak at Chicago Chop House, where oak-paneled walls feature more than 1,400 historic photos. Locals and tourists alike love Gibsons Bar & Steakhouse (1028 N. Rush St.), which offers tender, Prime-aged steaks in an old-fashioned steakhouse atmosphere.