A Title Over a Century in the Making

Walk into Daley’s Restaurant on any given morning and you’ll find vintage photos lining the walls, regulars greeted by name before they even sit down, and a menu that hasn’t strayed far from what’s kept people coming back since 1892. That’s not a typo. Daley’s has been feeding Woodlawn for more than 130 years, and since 2017, it’s held the title of the oldest restaurant in Chicago.

The oldest restaurant in Chicago isn’t a downtown institution or a tourist stop. It’s right here on Cottage Grove, in Woodlawn, still serving the same neighborhood it opened in.

From Ironworker’s Diner to Neighborhood Fixture

Daley’s story starts with John Daley, an Irish immigrant who came to Chicago to work construction on the city’s elevated rail line. In 1892, with the University of Chicago, the World’s Columbian Exposition, and the rail line all under construction nearby, Daley spotted an opportunity. Feeding hungry workers made more sense than swinging from steel beams in the Chicago cold, so he opened a small diner at 809 East 63rd Street.

One clarification worth making up front: this Daley has no relation to the Daley political family that includes two former Chicago mayors. It’s a coincidence of names that’s followed the restaurant for over a century.

By 1918, Daley sold the restaurant to two young Greek immigrants, waiter Tom Kyros and cook Paul Emmanuel, who’d both worked there under Daley. They kept it running and growing until 1932, when they set out to rebuild the aging building with a sturdier structure. Financing fell through mid-construction when the bank backing the project failed during the Great Depression. Daley’s sat as an empty lot for five years before Kyros and Emmanuel finally scraped together enough to finish the job in 1937.

A Restaurant Passed Down, Not Sold Off

What makes Daley’s rare isn’t just its age. It’s that the same family has run it since 1918. Ownership passed from Kyros to his son George, then to nephew George Politakis, then to cousin Nick Zee, and eventually to Nick’s son, Mike Zee, who’s led the restaurant since 2005. Zee started working in the Daley’s kitchen at 15 years old, the same way the family before him had.

That kind of continuity matters in a neighborhood that’s been through plenty of change. Woodlawn saw real disinvestment in the decades after the 1960s, and a lot of longtime businesses didn’t make it through. Daley’s did, largely by staying exactly what its regulars needed it to be.

What to Order

The menu at Daley’s reads like a love letter to homestyle cooking. Breakfast runs all day, and dinner starts as early as 10am to serve overnight staff from the nearby University of Chicago Medical Center coming off their shifts. Standouts include:

• Baked chicken with all the classic sides
• Creamy mac and cheese
• Slow-cooked collard greens
• Four different steak options
• Biscuits made from a recipe that’s stayed the same for 40 years

Nothing fancy, nothing overworked. Just food that tastes like it’s been perfected through decades of repetition.

More Than a Meal

Ask anyone who’s spent time at Daley’s and they’ll tell you the food is only half the draw. Staff span generations, students sit next to elders, and regulars slide into their usual booth like they’ve done it a thousand times, because many of them have. It’s the kind of place where a server remembers how you take your coffee before you’ve finished sitting down.

Woodlawn has always needed spaces like this, somewhere steady, familiar, and open to everybody who walks through the door. Daley’s has quietly filled that role for over a century.

Straight From the People

The stories people share about Daley’s tend to span generations, not just visits.

“The last time I visited this restaurant was over 20 years ago with my dad. The food was amazing then and amazing today. The staff, the vibe, and the food were perfect. I ordered biscuits and gravy and a side of bacon. Their biscuits and gravy was the best I’ve ever eaten. I will be going back again soon.”

— Nett Davis

“I have been coming to Daley’s for over 10 years. When they were across the street, I would go inside to stay warm and wait for the school bus. Now as an adult, I must get their fried chicken and waffles when I visit from Michigan. The chicken is so juicy, hot, fresh, and slides right off the bone.”

— Brianna Parks

“There are so many fond memories of this place near and dear to my heart. My grandmother, who transitioned, dined here often, and with my kids in tow when she babysat. The new place across the street looks absolutely amazing and there is so much room now. I’ll be back soon to try more of the menu.”

— Jataun Rollins

Still Standing, Still Serving

In 2019, Daley’s moved into a new building directly across the street, part of the Woodlawn Station development. It was one of the first new buildings the block had seen in decades. The restaurant sits about a mile from the Obama Presidential Center and right at the terminal stop of the CTA Green Line, easy to reach whether you’re coming from Hyde Park, downtown, or just down the block.

Daley’s earned the title of oldest restaurant in Chicago almost by outlasting everyone else, but longevity alone doesn’t explain why people keep coming back. That part comes down to the food, the service, and a family that’s kept showing up for over a hundred years.

Visit Daley’s Restaurant

Address: 6257 S. Cottage Grove Ave., Chicago, IL 60637

Hours: Open daily, 7am to 5pm

Phone: 773-643-6670

Website: daleysrestaurant.com

Social Media

Instagram: @daleysrestaurant

Facebook: Daley’s Restaurant

Delivery available via Uber Eats and Postmates.