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Where Route 66 Begins: Exploring the Start Sign in Chicago

  • Jenny Wallace
  • May 18
  • 2 min read

There’s something timeless and magnetic about beginnings—and for America’s most iconic road trip, it all begins at the corner of Adams Street and Michigan Avenue in the heart of downtown Chicago, Illinois.

Here, under the watchful eye of the city’s skyscrapers and the steady hum of urban life, the “Begin Historic Route 66” sign stands as a beacon to wanderers. It might look like just a street sign to passersby, but for Route 66 travelers, it’s a symbol of adventure, history, and the open road ahead.


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A Humble Marker with a Massive Legacy

Officially commissioned in 1926, Route 66 has become much more than just a highway—it’s a living story stitched across America’s landscape. The Chicago start sign isn't just a tourist stop; it’s the gateway to over 2,400 miles of nostalgic roadways, stretching across eight states and ending in sunny Santa Monica, California.

Standing at this sign, you’re stepping into a cultural corridor filled with retro diners, neon-lit motels, vintage gas stations, and small towns that still carry the soul of mid-century Americana. It’s a road that has inspired novels, songs, films, and even revival movements—each anchored to this single starting point.

Soak in the Surroundings

Don’t rush your visit. This isn’t just a photo op—it’s a moment. Take a breath and absorb the energy of the city before heading westward.

Within walking distance, you’ll find:

  • Millennium Park – Home of the famous “Bean” sculpture and sprawling public art.

  • The Art Institute of Chicago – A world-renowned museum housing masterpieces from Van Gogh to Warhol.

  • Lake Michigan’s shoreline – A beautiful backdrop that frames the city in shimmering blues.

Whether you’re starting a full cross-country journey or simply stopping by for a taste of Route 66, the experience starts here—with culture, history, and inspiration on every corner.

Insider Tip:

Go early in the morning to catch the golden light of sunrise illuminating the skyline. You’ll beat the crowds and capture stunning photos with that nostalgic, cinematic glow that perfectly suits the start of a legendary road.

Why It Matters

Route 66 is seeing a cultural revival—with film projects, augmented reality storytelling, and preservation efforts by organizations like the National Trust for Historic Preservation breathing new life into the route. What better time to explore its roots than now?

The “Begin Route 66” sign in Chicago isn’t just a location—it’s a launchpad for stories, both old and new. And your journey starts the moment you find yourself standing at that historic corner.

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