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, Illinois: The iconic "BEGIN Route 66" sign. This small, yet powerful, symbol marks the moment we leave behind the routine of everyday life and embark on a journey of memory and quiet wonder.

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. The urban energy of Chicago serves as a dramatic launchpad for the historic highway. Standing beneath the iconic "Begin" sign felt less like a simple start and more like a symbolic shedding of the urban hustle. The metallic curves of the Cloud Gate (The Bean) and the interactive nature of the Crown Fountain represented the modern, vibrant America we were leaving behind, while the open road promised the nostalgic past. This contrast—between the towering, glossy city and the humble two-lane road—is what makes the Illinois start so powerful. It grounds the entire journey in a moment of significant transition.

Cloud Gate (The Bean) Chicago

Chicago's Cloud Gate, the modern mirror reflecting the urban life left behind for the historic journey on Route 66.

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. Each stop carried echoes of the past—stories of travelers who once followed the same hopeful road west.


                                              

Bob Waldmire Van at Rt 66 Museum

Pontiac, Illinois: Bob Waldmire's iconic van, a centerpiece at the Route 66 Hall of Fame Museum, represents the free spirit and history recorded along the Mother Road.
Source: Wikimedia Commons, Creative Commons Attribution-ShareAlike 2.0 Generic


1. The Route 66 Hall of Fame Museum: A Living Archive of Memories

The Route 66 Hall of Fame Museum felt less like a simple display of highway artifacts and more like a living archive preserving the time and memory of the people who built their lives along this road. I was particularly moved by the stories of hope and disappointment embedded in the faded letters, photographs, and old license plates donated by countless travelers. Writing my own hopes for Route 66 in the guest book by the entrance felt like a precious moment, emphasizing how deeply this road is intertwined with personal history. I recommend giving yourself at least an hour and a half to wander, and make sure to listen to the staff's stories—they are the living history of the Mother Road.


Gemini Giant , Wilmington ILL

Wilmington, Illinois: The iconic Gemini Giant, a classic "Muffler Man" statue, symbolizes the mid-century optimism of the Mother Road. Its sheer size highlights the quiet wonder found along the route.

2. The Towering Gemini Giant: Space Age Optimism

In Wilmington, the towering fiberglass astronaut known as the Gemini Giant greeted us with a slightly faded but cheerful wave. This "Muffler Man" roadside advertising statue is a perfect example of the quirky, memorable icons that brought the highway's history to life. The Gemini Giant truly symbolizes the space-age optimism of the 1960s, standing as a massive, almost whimsical landmark against the wide Illinois sky. The contrast between the sheer scale of the statue and the quiet, flat landscape offered a moment of quiet wonder, perfectly matching our theme for the day.


The Abraham Lincoln Presidential Museum

Springfield, Illinois: A statue of Abraham Lincoln. This profound historical symbol connects the freedom of the open road with the weight of American identity explored at the Presidential Museum.

3. The Abraham Lincoln Presidential Museum: Profound Historical Identity

Further south in Springfield, the capital city offered a powerful historical contrast. Visiting the Abraham Lincoln Presidential Museum wasn't just a detour; it was a deeply moving experience that connected the Route 66 journey—a symbol of American mobility—to the profound history of American identity and the Civil War era. The museum’s immersive and emotional exhibits force you to reflect on the true weight of American history, offering a profound perspective that enriched the entire road trip experience.  

Collinsville, Illinois: The World's Largest Catsup Bottle. This colossal, whimsical landmark perfectly captures the unique, surprising roadside culture that makes the journey along Route 66 an adventure of quiet discovery.

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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