Chicago's Oldest Diner Has Been Serving Food Since 1892

The Windy City is something of a foodie destination — it takes its eats seriously, whether you're looking for an Anthony Bourdain-approved Italian beef or a Chicago-style hot dog, with its striking neon green relish. To that end, Chicago plays host to some pretty historic eateries, like The Berghoff Restaurant, which specializes in German food and opened in 1898, or The Walnut Room, situated on the seventh floor of a Macy's department store and opened in 1907. But for as long as those places have been around, the oldest restaurant in all of Chicago opened in 1892, and it's called Daley's Restaurant.

This historic south-side staple has witnessed some of the country's greatest upheavals and conflicts; it was opened in the late 19th century by an ironworker who had previously immigrated to the States from Ireland, John Daley. His entrepreneurial spirit saw an opportunity to feed his fellow construction workers, who were busy laying railroads, as well as the builders who would raise everything needed to house the 1893 World's Columbian Exposition. The University of Chicago was also being built at the same time, and Chicago was a hive of activity at that point.

John Daley's hard work paid off, and his restaurant quickly established itself as part of the fabric of the Woodlawn neighborhood. However, in 1918, Daley opted to sell the diner to two Greek immigrants, Tom Kyros and Paul Emmanual. Under their ownership, Daley's, whose name they decided not to change, continued to flourish, though the bank through which they had financed a loan failed in the 1930s. Daley's was forced to close, but Kyros and Emmanual managed to save up enough money on their own to reopen the diner in 1937. Daley's would stay in the Kyros family for the foreseeable future; as each older generation has retired, a member of the younger generation has stepped in to take their place.

The current co-owner, Mike Zar, has overseen some major changes at Daley's, most recently the 2019 move from its old East 63rd Street location to its current address just across the street on Cottage Grove Avenue, in a modern development called Woodlawn Station. With its contemporary design and industrial facade, as well as chandeliers hanging inside and TVs mounted on the walls, Daley's is a diner reimagined. However, if there is one thing that wouldn't change, Zar was determined to keep the expansive menu, which is a mix of diner classics and soul food, fully intact.

For it to stay in business for more than a century, Daley's Restaurant has had to bring the flavor through the decades. The current menu reflects classic diner dishes and soulful Southern staples, with its chicken and waffles standing out in particular. Part of the breakfast menu, the dish features a large Belgian waffle with plenty of butter and homemade syrup, plus five fried wings. One Google reviewer stated they were "sad to see the pile of empty bones, syrup[,] and crumbs when I was done. The waffle was crisp and tasty and the wings were crunchy and well seasoned."

The rest of the menu is just as packed with comfort food favorites, offering everything from golden cornmeal-crusted catfish fillets and homemade salmon patties to slow-cooked pot roast and shrimp and grits; you can even order a plate of liver and onions. Finally, if you need a sweet treat to finish off your meal, Daley's peach cobbler has been described as "amazing" by one Google reviewer, while someone on TripAdvisor said they "can't just buy one" because it's so delicious.