The 15 most iconic restaurants in Chicago

The most prominent Jewish deli in Chicago has operated for eight decades and though it received a facelift in 2016, little else about the experience has changed. Grab a tray and get in line, because the food is served cafeteria-style. The reason to come here is the famous corned beef, generously piled high on rye bread, but other standouts include the pastrami, potato pancakes and matzah ball soup. No matter what you order, you’re certain to leave full and satisfied.

The history of the humble Italian beef sandwich is murky but its popularity can be traced back to Al’s on Taylor Street. Though there are outposts all around Chicagoland, the original location—opened in 1938—remains a must-visit for both locals and tourists alike. The classic recipe calls for simmering thin slices of heavily seasoned roast beef in gravy and then loading it onto French bread, preferably alongside sweet or hot peppers. Eat it in the proper upright position while leaning over a counter to avoid getting messy.

Take a trip back in time to the Prohibition era at this vintage cocktail lounge in Uptown. Featuring live jazz every evening, the Green Mill has hosted celebrated names such as Billie Holiday and Von Freeman, and was also a favorite haunt of Al Capone. If you don't arrive early, long waits to get inside should be expected. But tough it out and you’ll be rewarded with enthralling musical performances, mean martinis and maybe even a seat at Capone’s old booth.

It may not be home to Chicago’s best burger (we’ll leave that open to debate), but there’s no denying the fact that the Billy Goat Tavern is a world-renowned restaurant, thanks in part to an appearance on Saturday Night Live as well as owner Billy Sianis placing a supposed Curse of the Billy Goat on the Chicago Cubs back in 1945. Today, it remains a reliable spot to get a no-frills “Cheezborger,” dressed with the toppings you want from the condiment station, plus a cold beer. And the flagship Michigan Avenue outpost is a bit of a hidden secret, tucked away in an underpass beneath the Mag Mile.

When you think of fried chicken in Chicago, the first place that usually comes to mind is Harold’s. Though the quality may vary between locations, the local chain is one of the city’s most famous institutions, with celebs, athletes and even President Obama among its countless fans. The food’s made to order, so you can expect the meat to turn out juicy, tender and enveloped by perfectly crisp skin every time. Of course, the chicken’s not complete without a dousing of mild sauce—a vinegary hot sauce that adds a bit of acidic zip and helps cut through the grease.

There are old-school spots, and then there’s the Berghoff. Family-owned and run for over 120 years, the German restaurant is notable for having secured the city’s first two liquor licenses after the repeal of prohibition and operating a mens-only bar until 1969. Today, the 45,000-square-foot space not only houses a restaurant, bar and (currently closed) café, but a microbrewery as well. Downtown office workers and those interested in a bit of Chicago history stop in regularly for cold pints and hearty plates of wiener schnitzel, sauerbraten and sausages.

Chicagoans head to this revered smoke shack next to the Calumet River on the far South Side for some of the city’s finest seafood. Whether it’s smoked salmon and trout or fried shrimp and scallops, you can’t go wrong with anything on the menu. Bring money as it’s cash only and be ready to eat on the sidewalk or in the car. The James Beard Foundation deemed the shack an American Classic in 2010.

Although Marshall Field’s is long gone, the wood-paneled restaurant inside the iconic local department store lives on. It’s one of the oldest eateries in Chicago, having been established in 1907, and also a popular destination once the holiday season rolls around. No visit to the Walnut Room would be complete without trying Mrs. Hering’s chicken pot pie, a recipe named after a former sales clerk that dates back to 1890.

A staple for late-night eats and hungry UIC students, Jim’s is beloved for its budget-friendly prices. The stand claims to be where the Maxwell Street Polish was born and you’ll find countless customers at all hours of the day enjoying the iconic sausage topped with mustard, grilled onions and hot peppers. Another must-try is the pork chop sandwich, which is unique because the meat is served bone-in on the bun—be careful where you bite!

Service with a smile and complimentary doughnut holes and Milk Duds attract folks to one of the oldest restaurants in Chicago. This greasy spoon is on the National Register of Historic Places, as it's in close proximity to the starting point of Route 66. The kitchen turns out reliable diner fare like jumbo omelets, fluffy pancakes and house-made baked goods.

Chicago isn’t exactly best known for barbecue, but the city’s South Side certainly has an identity of its own when it comes to smoking meats. At Lem’s, rib tips—a preferred cut in Chicago for its flavor and value—cooked in a custom glass smoker that looks like an aquarium is the specialty. Just follow the smells coming out of the smokestack and prepare to wait in line—the reward is worth it.

Now nearing its hundredth birthday, the Original Rainbow Cone has delighted generations upon generations of Chicagoans. The Beverly scoop shop–with additional locations at Navy Pier and the suburbs–is a requisite visit in the summertime. Pull over when you spot the bright pink building on Western Ave and head inside to discover the city’s most Instagram-friendly frozen treat. The namesake Rainbow Cone is a kaleidoscope of colors, containing slices of chocolate, strawberry, pistachio and Palmer House (vanilla with cherries and walnuts) ice cream plus orange sherbet.

Meat and potatoes are a Midwesterner’s best friends and there’s an abundance of steakhouses in the city to cut into prime beef. None, however, have been doing it longer than Gene & Georgetti. Opened in 1941, the timeless institution still ranks among the quintessential Chicago experiences. The steaks are wet-aged for at least three weeks and then simply broiled before being served in a classic, white-tablecloth setting.

Twelve-foot hot dog mascots, named after the original owners Maurie and Flaurie Berman, sit atop this legendary stand to welcome passersby in for a quick bite. Drive-in restaurants may be a relic of yesteryear but Superdawg has been around since 1948 and shows no signs of slowing down. Pull into an open space and place an order through the intercom; carhops will bring the food out so you don’t have to leave your vehicle. The signature item is, of course, the Superdawg, a pure beef hot dog dressed with mustard, green relish, Spanish onions, hot peppers, dill pickle spear and a wedge of pickled green tomato. 

Opened in 1921, this old school ice cream parlor is a charming time warp back to yesteryear. Nostalgic photos and Beatles memorabilia line the shelves, while the surprisingly lengthy menu boasts a variety of sundaes, banana splits, ice cream floats and more. If you’re looking for an experience you won’t soon forget, bring a group and order the 25-scoop sundae—you may need to be rolled out afterwards.