Every American city worth its salt now features a cluster of craft cocktail bars, farm-to-table restaurants, and artisanal coffee shops. But missing from a lot of this urban renewal is real history—places that connect generations in a city. Chicago, thankfully, has brought in the new while still embracing the old. So instead of sending you to Aviary, Publican and Intelligentsia for the new Chicago, we’re keeping it old school. These classic spots will take you back decades, to when Windy City and the rest of the country had much different ideas about going out for dinner and what we considered to be good food. Most of these places have changed very little over the years, though the hot dog shack without running water is no longer a shack—and now has running water.
Billy Goat Tavern
The Chicago Cubs may never win a World Series thanks to this restaurant’s goat. William Sianis founded the place in 1934, and shortly after, a goat fell off a passing truck and wandered in. Like any restaurant owner, he adopted it, and like any Cubs fan, he bought it a ticket for Game 4 of the World Series against the Detroit Tigers in 1945. He and the goat were turned away from Wrigley Field due to the goat’s odor, and so he cursed the team, saying “The Cubs ain’t gonna win no more.” Both the curse and the restaurant have lived on; the latter moved to its current home, in 1964, where it quickly became popular with journalists thanks to its location between the Tribune Tower and the old Sun-Times building. It’s a restaurant with better ambience and folklore than actual food, but do yourself a favor and order a “cheezborger” anyway. Just don’t expect to get any fries.
Since 1962, Nuevo Leon has served some of the best traditional Mexican food in a city chock full of great Mexican food. The Guitérrez family, which still runs the restaurant, opened the place right at the start of the boom in the Mexican population in Pilsen. Since then, Nuevo Leon has specialized in Northern Mexican cuisine, like chilaquiles, which make a perfect breakfast, and tacos de sabinas with ribeye, served on house-made tortillas.
There’s a lot of folklore swirling around gyros, and some of it says they originated in Chicago, where the country’s main gyros factories have been based since the 70s. Before the cylinders of meat were mass-produced, they were made in only a few restaurant kitchens, including the Parthenon, a favorite for Greek food since it opened in 1968. The Parthenon also plays host to another origin story—that of flaming saganaki, the fried cheese soaked in brandy lit on fire tableside, accompanied by waiters’ shouts of “opa!”
Harold’s Chicken Shack
Two years before Colonel Sanders franchised his first Kentucky Fried Chicken, Harold Pierce opened his chicken shack on Chicago’s South Side. The restaurant, founded in 1950, grew out of Pierce’s first venture, H&H, a restaurant specializing in dumplings and chicken feet. Pierce thought he might adapt his recipe for fried chicken proper, and Gene Rosen, owner of a neighborhood poultry shop, gave Pierce some chickens to try it out. Once he did, he opened the first Harold’s, at 47th and Greenwood, bringing fast food to a mostly black neighborhood that fast-food chains avoided.
The exact recipe doesn’t endure today, but that’s what Pierce wanted; each franchise owner is given control over cooking, prices, and the menu itself. His only regulation, at first, was that franchisees got their chickens from Rosen. Today, there are more than 62 Harold’s, most of them in Chicago, leaving plenty of room for debate over the best one. Mike Sula, in the Chicago Reader, tried 35 of them, and called a narrow victory for number 55.
Gene and Georgetti
This throwback steakhouse in River North is still popular with politicians and the business crowd. The steaks are straightforward—little seasoning or butter—big, and tender. The restaurant is still owned by family of one of the founders, Gene Michelotti, who started the restaurant in 1941 with Alfredo Federighi (nicknamed Georgetti, after an Italian cyclist). The place has kept its 1941 decor, sticking with the wood paneling and red-leather booths. The building itself has a longer pedigree; the wood structure was built in 1873, a year after the Chicago Fire, and right before the no-wood-buildings ordinance went into effect.
Around the corner from the old Playboy Club’s is Geja’s, the original fondue place and Chicago’s first wine bar. The restaurant has been in its current basement space since 1971. In 1969, four years after he founded Geja’s, John Davis founded Geja’s Wine Society, laying the groundwork for the restaurant that today is known as one of Chicago’s most romantic spots. The place claims to have been the scene of more than 127,671 first dates; at those and other less stressful meals, its served more than 290 tons of cheese fondue and 926,187 bottles of wine.
Twin Anchors is one of Chicago’s longest lasting ribs places for a reason. The ribs are delicious, the meat falls off the bone and the barbecue sauce adds the perfect amount of flavor without being overpowering. And this spot has been around before the Anchors even existed. In the early 1900s Schlitz donated the bar to the building’s original owners. Then during Prohibition, the space became a not-so-subtly named speakeasy called Tante Lee Soft Drinks, and then, in 1932, Twin Anchors. It started out as just a bar and became a restaurant after the owner and his wife realized the ribs they served on Sunday nights could sustain a full-fledged eatery. In the 1950s, it became one of Frank Sinatra’s favorites; his presence is still felt in the jukebox. But before picking any song to play, be advised of the restaurant’s “positively no dancing!” rule.
Chiu Quon Bakery
The best place to get barbecue pork buns is also the best place to get sweet coconut buns and also the best place to get pickled chicken feet. There’s quite a bit more in this bakery’s bakery cases, whose harsh lighting is done a favor by the buns, whose dough casts a warm reflection, and most of it is delicious—especially those buns, whose fillings you can discern by the colors dotted on their tops. The original location, opened in 1988, is the oldest bakery in Chinatown and is now joined by an offshoot in Uptown.
Richard Melman began his Lettuce Entertain You restaurant empire with R.J. Grunt’s. Like Geja’s, it’s just around the corner from the last Playboy Club, and also like Geja’s, it has its eye on romance—or at least once did. Melman intended for the restaurant, opened in 1971, to be a bumping singles scene. Now, it’s frequented by all sorts of people, including families who head there after a trip to the Lincoln Park Zoo. They come for the fried-onions-and-bleu-cheese-topped Gruntburgers, on the menu since the place opened, and the lengthy salad bar, one of the world’s firsts.
The Berghoff was originally intended to be a showcase for Berghoff’s Beer, made by Herman Berghoff and his sons in Indiana. They brought their beer to Chicago for the 1893 World’s Fair and, five years later, opened the Berghoff café, where a beer was a nickel and sandwiches were free. It stayed open during Prohibition, when it served near beer and Bergo soda, including the still-popular Berghoff root beer. When Prohibition was repealed, the Berghoff got Chicago’s first liquor license, and things returned to normal—that is, if normal was a restaurant with a men’s only bar. The restaurant’s sex segregation ended in 1969 after a Gloria Steinem-led group of NOW members insisted on being served at the men’s bar. Not much has changed since then, with the restaurant serving men and women alike standard German fare like wiener schnitzel and beer.
The original Portillo’s, a trailer in Villa Park then called The Dog House, didn’t have any running water when it opened in 1963; the owner, Dick Portillo, relied on a 250-foot hose. The place has come a long way since then, with locations now in Illinois, Indiana, California, and Arizona. But there’s nothing like the original, which, unfortunately, isn’t technically in the city but in Villa Park, a suburb west of the city originally built as a place for Ovaltine factory workers to live. There, you can get a Chicago-style hot dog with a Vienna Beef wiener made specifically of Portillo’s. The snappy dog comes with classic Chicago fixings: pickle, relish, yellow mustard, tomato, sport peppers, chopped white onions, all in a poppy seed bun—and under no circumstances with ketchup.