The 10 Most Iconic Restaurants in Chicago – Time Out

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Timeless and revered, these iconic spots haven't skipped a beat over the years.
Chicago’s incredible wealth of restaurants make the city a world-class dining destination—and although buzzy newcomers get much of the attention, it’s the longstanding spots that keep the city fueled and running. Some of them are among the best restaurants in Chicago, while others are hot dog experts. They’ve all been around for decades (or more than a century in a few cases) and are classic time capsules that belong on the dining bucket list of locals and tourists alike. Several of Chicago’s most famous dishes are represented, like Italian beef and Polish sausages. There’s even a James Beard-recognized seafood shack that smokes its own fish on site, as well as a prohibition-era cocktail lounge once frequented by Al Capone. So start mapping out a route, because this guide to the most iconic restaurants in Chicago will take you everywhere from Norwood Park to South Deering.
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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.
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.
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.
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. 
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