8/11/25

24 Hours in Chicago, thebigda Style

A 24-Hour Walk Through Chicago’s Streets, Memories, and Unexpected Salads
24 Hours in Chicago, thebigda Style

What happens when the downtown West Palm Beach ‘walk and talker’, private equity powerhouse, and hot dog world record holder returns to his hometown of Chicago for just 24 hours?

You get a whirlwind of business, nostalgia, and a whole lot of steps.

The Mission: Business (But Make It Brief)

Dan Abbate—aka thebigda—landed in Chicago with one goal: a meeting with the CEO of 😉😊  Bank. Mission accomplished. Handshakes, strategy, vision. Done.

But Dan doesn’t just fly in and out. He walks in and out. Literally.

The Walk Begins

With business wrapped, thebigda did what he does best: walk. Six hours of it. Through the city he once called home, phone in hand, wife Kelly on the line, and memories around every corner.

From the Wicker Park/Bucktown to the lakefront, from old neighborhoods to the statue of Harry Caray at Wrigley Field, Dan retraced the steps of his younger self. He noticed the changes—like the mega-building near Wrigley that replaced the cozy neighborhood vibe—and the things that hadn’t changed at all, like the shabby little parking booth on Clark Street that somehow survived unknown decades of Chicago winters and Cubs seasons.

A Toast to the Past (Sort Of)

One bittersweet moment: discovering that Chicago’s Blarney Stone, a college-era foosball-and-beer haunt, had closed its doors. RIP to the memories (and the foosball victories).

Bowling, But Make It Healthy

The evening brought Dan back to business—sort of. He reconnected with the bank crew at Diversey Bowl, where they roll strikes in a Monday night league. Dan didn’t bowl, but he did embark on a different kind of challenge: finding a healthy meal on a bowling alley menu. After scanning for something green, he landed on a Cobb salad. Respect. “In West Palm, you can get a great salad on every corner,” Dan said. “In Chicago? You’ve got to work for it.”

The Hot Dog King Returns

Of course, if Dan had wanted to go full Chicago, he could’ve hit Lou Malnati’s for deep dish, Pequod’s for that caramelized crust, or literally any corner for a Vienna Beef hot dog—which, by the way, he insists are superior to New York’s. And he would know. He’s the Guinness World Record holder for the largest commercially available hot dog ever made. (Yes, really. Here’s the proof).

Walk. Talk. Think.

Whether in West Palm or walking the streets of Chicago, Dan’s mission is the same: help people do what they love. He’s built businesses, mentored entrepreneurs, and learned that success doesn’t always equal happiness—but authenticity does. And sometimes, authenticity looks like a six-hour walk, a salad at a bowling alley, and a quiet moment in front of a statue of Harry Caray.

Coming soon: thebigda Podcast
Where walking, wisdom, and wild stories collide.

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