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. We’re talking Chicago-style hot dogs, deep-dish pizza and the beloved Italian beef sandwich, but that’s only the beginning.
For a memorable experience, stop by one of Chicago's classic steakhouses or embrace local Puerto Rican traditions with a jibarito. 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.”
Expect extra toppings: chopped onions, sweet pickle relish, sliced tomatoes, sport peppers and celery salt. Chicago favors Vienna Beef, so expect a snappy hot dog with a hint of garlic.
There is no shortage of hot dogs in the Windy City. Take a stroll downtown and you’ll see plenty of hot dog stands, plus dedicated restaurants that offer original takes on the classic Chicago dog.
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.
If you’re ready for something new, try the memorable dogs at local favorite Devil Dawgs (767 S. State Street and other locations), where hot dogs can be topped with green chiles or even remoulade.
Deep-Dish Pizza
In Chicago, the hot dog is far from the only food to get its own unique spin. Pizza is another local icon and, in Chicago, it can look a lot different from your typical pie. 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 and for a good reason: 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 of this reverse-engineered pizza? A double helping of delicious flavors atop a bowl-like crust that is crisp and sometimes buttery on the outside. Tavern-style is actually more popular among most residents, but for the true Chicago experience, you have to try at least one deep dish pizza.
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. (1120 N State St).
Join the legions of Pequod's enthusiasts and try the caramelized crust. Visitors debate whether it qualifies as deep dish or pan pizza, but there's no denying it's delicious. The Lincoln Park location (2207 N. Clybourn Ave) is always busy, so be prepared to order a drink next door at Beck’s while you wait. Otherwise, skip the line and head north to the Morton Grove location (8520 Fernald Ave), which, although still busy, offers its own charm with its retro digs.
Italian Beef
Move over hot dog: the Italian beef sandwich is even more memorable in all its juicy, messy glory. It’s packed with thinly-sliced, seasoned beef — 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.) also gets raves for its Italian beef.
Johnnie's Beef (7500 W North Ave, Elmwood Park) is also worth a visit, although you’ll need to bring cash. Amp up your order with the Italian Sausage Combo, which decks out your Italian beef sandwich with a juicy, char-grilled sausage.
Jibarito
There's no sandwich quite like the jibarito and no better place to enjoy one than in Chicago (and, specifically, the Humboldt Park neighborhood). Replacing bread with fried green plantains, this culinary wonder is often credited to Juan "Peter" Figueroa, who saw opportunity in the form of a Puerto Rican-American sandwich fusion.
As the home of the original jibarito, Borinquen (3811 N. Western Ave) remains a top destination, although Omarcito's Latin Cafe (3801 W. Fullerton Ave) also gets rave reviews. Pair your jibarito with an agua fresca for a refreshing summer meal.
Snacks
When the urge to snack strikes, head to one of many Garrett Popcorn Shops (like the 173 N. Michigan Ave. store near Grant Park). This beloved shop has been popcorn heaven since 1949. Year-round varieties include plain, buttery and nut-and-caramel mixes, but nothing beats the sweet-and-salty Garrett Mix, featuring rich caramel and cheese flavors.
If hot summer strolls have 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.
Chicago residents also love a rich cheesecake and, when cravings hit, nothing satisfies quite like Eli's. Cheesecake's available by the slice, but, once you have a taste, you'll want to order a full cake.
Steak
Chicago's history was heavily influenced by the meatpacking industry, as you can tell by its sandwich specialties. That being said, not all culinary greats are enclosed in a bun. Go classy with an upscale steakhouse and add a Martini for good measure.
Step into Chicago's past as you enjoy a dry-aged Prime steak at Chicago Chop House (60 W. Ontario St.), where the oak-paneled walls are adorned with over 1,400 historic photos. Otherwise, stop by Gibsons Bar & Steakhouse (1028 N. Rush St.) for tender, Prime-aged steaks in an old-fashioned steakhouse atmosphere.
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