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  1. Sep 21, 2023 · Visit Chicago's most iconic restaurants for some top-notch Italian beef, steaks, corned beef and much more.

    • Jim's Original

      A little walk-up shack on the UIC Campus with no seating,...

    • Twin Anchors Restaurant & Tavern
    • Italian Village
    • Orange Garden Restaurant
    • Lou Mitchell’s
    • Green Door Tavern
    • Pompei
    • The Walnut Room
    • The Berghoff Restaurant
    • Daley’s Restaurant
    • The Takeaway

    photo source: Flickr The Twin Anchors Restaurant & Tavernhas remained a classic since it opened in 1932, even though it changed owners in the late 70s. Since it opened, it’s been famous for baked, Chicago-style prime baby back ribs. The décor of the restaurant is nautical themed and has always been that way. The old speakeasy was turned into a bar,...

    photo source: Flickr This won’t be the last time Little Italy peeks in on our list. This downtown Chicago restaurant has the décor to match its history as a 1927 historical Italian villa in the heart of the windy city. They’re known for classic Italian fare such as their meat sauce, cannelloni, Bolognese, sausage, ravioli, and more. The oldest Ital...

    photo source: Flickr The Orange Garden Restaurantis the oldest Chinese restaurant in Chicago, opening its doors back in 1926. It has become famous for traditional Cantonese cooking, old-fashioned décor, and huge portions. Predating the People’s of Republic of China by decades, the Orange Garden Restaurant’s food is rooted in the classics. Favorites...

    photo source: Flickr Since 1923, Lou Mitchell’shas been a famous neighborhood hotspot for visiting celebrities, journalists, politicians, and sports figures. The restaurant sports a variety of fare, including skillet breakfasts, homemade savory and sweet pies, game meat, fresh oysters, and more. The smell of baked bread drifting down W Jackson Blvd...

    photo source: Wikimedia Commons The Green Door Tavernis arguably Chicago’s oldest drinking establishment, with a building that goes all the way back to 1872. The restaurant and bar that currently resides there, however, opened in 1921. It’s named for the green door that became its most famous attribute during Prohibition, when it served as a signal...

    photo source: Pompeiusa Pompei, like many neighborhood restaurants, is an Italian eatery known for fresh pizza, daily baked bread, and amazing Italian desserts. They’ve moved twice over the years throughout Chicago’s Little Italy and have three separate locations. However, the fourth generation Davinos that run the oldest location, founded in 1909,...

    photo source: Flickr The Walnut Roomis an eclectic, slightly more upscale dining room known for being the first restaurant ever opened in a department store. The Walnut Room is now a Macy’s institution. Eating there is like sightseeing in the 1800s, since the wood paneling, high ceilings, marble fountains, and other décor have remained trapped in t...

    photo source: Flickr The Berghoff Restaurantwas opened in 1898 by a family man named Herman Berghoff. It’s stayed in his family since then, serving signature German lager in steins and offering up authentic cuisine from his homeland. After a brief closure in 2006, the restaurant reopened with three distinct sections, including a bar, restaurant, an...

    photo source: Yelp The oldest restaurant in Chicago is Daley’s Restaurant. This old family-run city staple had been at the same location on 63rdstreet since it opened in 1892. In 2019, it relocated across the street to a modern location, but is still run by the same family and still serves the same classic food. John Daley, an Irish immigrant, open...

    The oldest Chicago restaurants have been feeding their regular patrons and celebrity guests for decades, some over a century. Though many have moved or changed hands from their original digs down in the old neighborhood, they remain institutions that define the windy city for its regulars and tourists. They are the beating heart of Chicago, from th...

  2. Oct 26, 2023 · Hidden in the middle of a residential block in Old Town, Twin Anchors is a family-friendly restaurant that’s crowded on the weekends, with seasonal cocktails, and barbecue ribs that come with a...

  3. Old Town Restaurants - Chicago, IL: See 2,316 Tripadvisor traveler reviews of 2,316 restaurants in Chicago Old Town and search by cuisine, price, and more.

  4. Book now at Historic restaurants near me in Chicago on OpenTable. Explore reviews, menus & photos and find the perfect spot for any occasion.

  5. 18 hours ago · Manny’s Deli. South Loop. Chicago’s quintessential Jewish deli is a cafeteria-style affair that’s been serving up piled-high pastrami sandwiches, matzo ball soup and brisket since 1942. The diverse crowd includes a mix of locals, tourists and usually a stumping politician or two. 1141 S. Jefferson St.

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  7. May 17, 2023 · Restaurants. Old-School Chicago Is Alive and Well at These Classic Restaurants. These Windy City institutions include century-old cafeterias, drive-ins, and more. By Matt Kirouac. Updated on...

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