Route 66 part 1: Chicago to Springfield | Illinois Road Trip

Route 66 part 1: Chicago to Springfield | Illinois Road Trip

📍 Part 1 — Chicago to Springfield

  • Starting Point: Chicago, Illinois (Route 66 “Begin” Sign)
  • Main Highlights: Millennium Park, The Bean, Crown Fountain
  • Route 66 Stops: Joliet · Pontiac · Springfield
  • Must-Visit: Route 66 Hall of Fame Museum · Gemini Giant · Abraham Lincoln Presidential Museum
  • Distance: Approx. 200 miles (320 km)
  • Travel Mood: Light-hearted, excited, free — the joy of finally beginning the long-held dream
  • Theme of the Day: Leaving behind the weight of routine and stepping into quiet wonder
Route 66 map showing the full stretch from Chicago to Santa Monica, the historic Mother Road of America.

Following the Echoes of Time — My Journey on Route 66

Route 66, often called The Mother Road, has long stood as a symbol of America’s restless spirit — a ribbon of highway that carried dreamers, wanderers, and hopeful hearts across the country. Stretching 2,448 miles from Chicago to Santa Monica, it moves through eight states, connecting landscapes filled with memory, history, and wide-open skies.

For me, this wasn’t simply a road trip — it felt like a quiet pilgrimage. Crossing America had been a dream tucked away for years, hidden beneath responsibilities and everyday routines. But sometimes, a small inner voice whispers, “It’s time.” And so, with our old car packed and our hearts surprisingly light, we set off.

Route 66 Begin sign in downtown Chicago marking the official starting point of the Mother Road.
Chicago — The Beginning of Route 66

We stood before the Route 66 “Begin” sign in downtown Chicago — a small sign, yet a powerful symbol. Behind us, the city hummed with its usual rhythm, but in that moment time seemed to slow. Walking past familiar places — the Bean at Millennium Park, Crown Fountain, and the soaring skyline — I felt a mix of excitement and calmness, as if I were both leaving and returning at once.

There was something liberating about that morning. The weight I had carried for so long felt lighter, as if the simple act of stepping onto this road opened a small window of freedom inside me. The anticipation of the unknown made me feel almost childlike again — curious, hopeful, and ready.

As we drove out of Chicago and into Illinois, the scenery shifted from city streets to quieter landscapes. We passed through Joliet, Pontiac, and Springfield, stopping at some of Route 66’s beloved icons: the Route 66 Hall of Fame Museum in Pontiac, the Abraham Lincoln Presidential Museum in Springfield, and the towering Gemini Giant, standing under the wide Illinois sky. Each stop carried echoes of the past — stories of travelers who once followed the same hopeful road west.

Route 66 Hall of Fame and Museum in Pontiac, Illinois, a classic landmark along the Illinois stretch of Route 66.
Pontiac, Illinois — Route 66 Hall of Fame Museum

Somewhere along that long stretch of highway, I realized that the meaning of this journey wasn’t tied to reaching Santa Monica. It lived in the simple moments — the sound of wind through open windows, sunlight flickering across the dashboard, and the quiet presence of forgotten towns slowly passing by.

Like life itself, the beauty wasn’t in the destination, but in the stillness of the moments we often overlook.

“Sometimes, the road doesn’t lead us somewhere new — it simply brings us back to ourselves.”


👉 Continue to Day 2: Springfield → St. Louis ----Back to Route 66 Series

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