From Navy Pier, Ryan Chiaverini makes stops at Lou Mitchell's, Lulu's Hot Dogs on Route 66 trek through Chicago to Will County

CHICAGO (WLS) — Route 66 turns 100 in 2026, and ABC 7 Chicago is honoring the milestone with a special feature series titled “Pier to Pier: Celebrating 100 Years of Route 66.”

In early June, Ryan Chiaverini and his traveling team, dubbed the “Sidekicks on 66,” set off from the road’s ceremonial starting point at Navy Pier. Their ride for the journey was a new Hyundai Palisade, showing just 22 miles on the odometer.

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From there, the crew passed the historic 1937 starting location at Michigan Avenue and Adams Street, cruised by Chicago institution The Berghoff, and then made a stop at Lou Mitchell’s, the landmark diner whose glowing neon sign has long promised the “world’s finest coffee.”

“Lou Mitchell really was a pioneer in many ways in what he did,” said Nick Thanas, owner of Lou Mitchell’s. “Skillet eggs and Greek toast: Those things were created really under his wing. I mean a lot of this stuff came from our culture, and he brought it to the table.”

The road trip continued with lunch at Lulu’s Hot Dogs and a sweet stop at Ferrara Bakery before the group left Chicago for Will County. Along the way, they snapped photos at Route 66 Park in Joliet, posed beside the Blues Brothers statues in Elwood and made their way to Wilmington, a community that proudly embraces its place along the Mother Road.

“Wilmington is really one of the first small towns along Route 66, where you really start stretching your legs and getting outside of the city of Chicago,” said Greg Peerbolte, CEO of the Joliet Historical Museum. “So, you have a lot of small-town charm and just a beautiful bunch of small and eclectic shops, art galleries and restaurants.”

Wilmington’s best-known roadside icon is the Gemini Giant, a towering 30-foot “muffler man” originally installed at the Launching Pad Restaurant in the 1960s to draw in visitors. Today, the statue stands at South Island Park, welcoming a new generation of Route 66 travelers with a dedicated gift shop and even a namesake beer served at Nelly’s On Route 66 and Old School Brewing.

“We have our beer, which is ‘Gemini’s Reentry,’ which is a golden ale,” said Jay Hill, bar manager at Old School Brewing. “It utilizes Gemini hops and so we released that beer right when the Gemini came back.”

For Chiaverini and the crew, it was one pier down and one to go in Santa Monica. But there was still plenty more to see over the next 2,300 miles.

“Pier To Pier: Celebrating 100 Years of Route 66” is sponsored by Hyundai.

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