There are old Chicago restaurants, and then there are classic ones—old in a way that captures a piece of the city’s history, or even its soul. These 10 local institutions feature delicious food and warm atmospheres that have kept their doors open and chairs full for decades. From steak to deep dish pizza, these classics go beyond food to sum up where this city came from.
Gene & Georgetti
Opened in 1941. The city’s oldest Italian steakhouse is home to politicos, fixers and other Chicago types, with a menu that’s a museum of vintage Chicago dining (wedge salad, Shrimp DeJonghe). Non-regulars are almost always sent to the less desirable second floor, but snag a downstairs spot by heading straight for the bar and dining there.
Opened in 1898. Last survivor of an era when hearty German food and beer was the epitome of a fine night out. Today the menu at this restaurant mixes German and contemporary American dishes. Hoist a lager at the bar on the side, which was known as the Men’s Bar (strictly enforced) until 1969, when the bartenders finally admitted women—by pretending not to notice and calling them “Sir.”
Opened in 1927. A multi-level complex launched at the height of Prohibition (when we’re sure you couldn’t have had a glass of Chianti there). Get romantic at wildly contemporary Vivere, feel nostalgic at old school pasta joint The Village, or go traditional with seafood and chops in the basement La Cantina Enoteca.
Manny's Coffee Shop and Deli
Opened in 1942. Last remaining sign of a onetime Jewish enclave just south of downtown, this cafeteria-style deli has been steaming and slicing its own corned beef and pastrami since the 1940s, along with comfort food favorites like short ribs. Banter with Gino, king of corned beef slicers, to get your sandwich just the way you want it.
Opened in 1977. Famous for baby back ribs, but really patronized for the whole range of American classics from chops to Caesar salads, Carson’s passes on the power-dinner atmosphere of most Chicago steakhouses for the everybody’s-welcome attitude of a midwestern supper club. Get comfy with two especially good comfort food sides: au gratin potatoes and the freshly-baked cornbread.
Gibsons Bar & Steakhouse
Opened in 1989. Steakhouses are everywhere in Chicago, but the city’s high-rollers know that if you’re making a big deal, you make it over red meat at Gibsons. (And if you want to land a high-roller as your next husband, Gibsons is where you go for that, too.) Share the 48-oz. porterhouse, the signature mega-cut since it opened defying the low-fat trends of the day.
Harry Caray's Italian Steakhouse
Opened in 1987. With the help of the legendary Cubs broadcaster, this restaurant found the perfect midpoint between Chicago steakhouse and sports bar on opening day—and has filled the bleachers ever since. Scout out some remarkable sports memorabilia on display, like the foul ball that cost the Cubs the playoffs in 2003. The building that houses the restaurant is itself a piece of history, an architectural landmark that was also once the home of Frank Nitti, Al Capone's infamous "enforcer."
Opened in 1984. The line between neighborhood red sauce Italian joints and artisanal Italian fine dining in Chicago was marked by the opening of Spiaggia, which still sets the standard for Italian with finesse and grace as it approaches its 30th anniversary. On a budget, Cafe Spiaggia offers a more casual version with the same spectacular lake view. Savor the unimprovably delicate pastas made in house every day by pretty much the same ladies in the kitchen since it opened.
Opened in 1991. Several local pizza chains can legitimately claim descent from the invention of Chicago deep dish by Rudy Malnati Sr. at Pizzeria Uno in the 1940s, but this one’s original location has the added bonus of Rudy Jr. himself holding court in its traditional Rat Pack-era tavern atmosphere. Warm up before your pizza (which takes a half hour plus) arrives with the wonderfully gooey spinach artichoke dip.
Mr. Beef on Orleans
Opened in 1978. Savory, juicy Italian-seasoned beef on a hard roll is Chicago’s distinctive local sandwich, and Jay Leno’s endorsement confirmed for visitors what locals already knew about this top-tier beef stand in River North. Pile on the giardinera, the spicy, oily mix of celery, peppers and other vegetables that’s unique to every Italian beef stand—and the neverending source of who’s-got-the-best? debates.
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