by Benny · 14 places · 11 dishes · Updated Aug 6, 2026
The old guard of Chicago dining: century-old dining rooms, the birthplace of deep dish, the first Italian beef, and the taverns and diners that made the city's food famous.
to track which of these you’ve been to.
Loop German $$
German restaurant in the Loop founded in 1898 by Herman Berghoff and still run by the family, with its stained glass and checkerboard floors intact.
What to order
The German classic both guides call out on the menu.
Logan Square Dessert / Bakery $$
Bucktown ice cream parlor and candy shop serving sundaes since 1921, complete with Tiffany lamps and tabletop jukeboxes.
What to order
The retro parlor classic The Infatuation highlights.
Hyde Park American $$
Cafeteria-style Hyde Park restaurant open since 1921, famous as a favorite of Barack Obama during his Hyde Park years.
What to order
The tray-line order Tasting Table calls out.
Near West Side American $$
Diner at the start of Route 66 open since 1923, on the National Register of Historic Places and still handing out free donut holes to waiting guests.
Loop Italian $$$
The original 1927 dining room of the Loop's Italian Village complex — Chicago's oldest Italian restaurant, run by four generations of the same family.
Near West Side Italian $$
Family-owned Little Italy restaurant since 1930 — no sign, chalkboard menus — recognized by the James Beard Foundation as one of America's Classics.
What to order
The signature dish both guides name.
Lincoln Park American $$
Old Town tavern serving ribs since 1932, famously a Frank Sinatra hangout.
What to order
The ribs with zesty sauce the tavern has been known for since the 1930s.
Near North Side American
The original subterranean location under Michigan Avenue, open since 1934 — home of the Cubs curse legend and the tavern that inspired SNL's 'cheezborger' sketch.
Near West Side American $
The original Taylor Street stand, opened in 1938 and credited as possibly the first Italian beef in Chicago.
What to order
The sandwich the stand is credited with originating.
Near North Side Italian $$$
Chicago's oldest steakhouse, open in River North since 1941, with vintage decor and decades-long regulars.
What to order
The house specialty The Infatuation names alongside the steaks.
Near West Side American $$
Family-owned Jewish deli in the South Loop since 1942, still serving cafeteria-style off the line.
What to order
The carving-station classic Manny's is known for.
Near North Side Italian / Pizza
Opened in 1943 by Ike Sewell and Ric Riccardo; widely credited as the birthplace of Chicago deep-dish pizza (authorship of the recipe is debated), and the original location still operates.
What to order
The dish first served here in 1943 that defined Chicago-style pizza.
Norwood Park American $$
Carhop drive-in at Milwaukee and Devon since May 1948, still ordering through speaker boxes under the rooftop hot dog statues.
What to order
The namesake all-beef hot dog served in its signature box.
The house cheeseburger named on Superdawg's own site.
Loop American $$
Opened in 1907 inside Marshall Field's (now Macy's) — the oldest operating department-store restaurant in the country, famous for its holiday Christmas tree.
Curated by
Caprarius
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