Lord Colliers Active Retirement Life

It has been twenty years since my last visit to Chicago—a snowy Thanksgiving trip that couldn’t be further from the spring energy I’m feeling today. Chicago has always been one of my favorite cities; there is an undeniable “high-performance” energy here, a mix of architectural muscle and deep-rooted history that makes it the only fitting place to begin a journey like this.

The Chicago Send-Off

Before hitting the road, I revisited the skyline that defines American architecture. Chicago is a city born of fire; after the Great Blaze of 1871, it reinvented itself as the birthplace of the skyscraper, a legacy you feel standing among the giants:

• The River Tour: An essential “canyon” perspective of the city’s growth and engineering marvels.
• The Giants: Contrasting the modern glass of Trump Tower with the dark, historic frame of the Willis (Sears) Tower.
• The Tribune Tower: Embedded in its walls are stones from across the globe. I sought out the fragments from Edinburgh Castle and St. Andrews—my mother was born in Scotland, and touching those pieces of her heritage felt like a vital bridge between my family’s past and this new American adventure.

Fueling Up: Lou Mitchell’s

You can’t officially start Route 66 on an empty stomach, so I headed to the legendary Lou Mitchell’s on Jackson Boulevard. Serving hungry travelers since 1923—three years before Route 66 was even commissioned—it is the quintessential “first stop.” There’s nothing quite like their world-famous omelets and the tradition of getting a Milk Dang and a donut hole while you wait. It feels like stepping back into the golden age of travel.

The First 100 Miles

The drive from Chicago to Pontiac is roughly 100 miles, a stretch that follows the historic “Pontiac Trail.” Leaving the “L” behind, I followed the alignment down Ogden Avenue through Cicero, eventually connecting to Route 4—the paved predecessor to the Mother Road. Passing through Joliet and Dwight, the hum of the city is replaced by the steady pulse of the Illinois cornfields.

Arrival in Pontiac: A Town that Embraces the Road

Pontiac (founded in 1837 and named after the legendary Ottawa Chief) was a vital stop on the Chicago & Alton Railroad long before the pavement arrived. Even Abraham Lincoln spent time here, famously once getting snowbound and needing a rescue by sled!

Today, the town lives and breathes the road:

• Route 66 Association Hall of Fame & Museum: A treasure trove of artifacts, including Bob Waldmire’s legendary “Road Yacht” bus.
• The Murals & Bridges: I spent the afternoon walking the downtown “Walldogs” murals and crossing the historic swinging bridges over the Vermilion River—a quiet, bouncing relic of the early 1900s.

First Night Under the Stars

To truly ground this experience, I’ve traded a hotel room for a campsite at Livingston County. My first night on Route 66 isn’t spent in a city, but under a wide Illinois sky. There is a specific kind of stillness out here that tells me the “Third Act” of this journey is going to be something special.