🏁 1. Chicago – The Official Start of Route 66

  • Route 66 Begin Sign (Adams St & Michigan Ave): Get your iconic starting photo!

  • Art Institute of Chicago: Not Route 66-specific, but a treasure trove of American and world art.

  • Lou Mitchell’s Restaurant (open since 1923): Historic diner where many began their Route 66 journey.

  • Union Station: Step into classic 1920s architecture—think "The Untouchables."

🏙️ 2. Joliet – Blues, Cars & Prisons

  • Joliet Area Historical Museum & Route 66 Welcome Center: Fantastic intro to the Illinois stretch of the road.

  • Rialto Square Theatre: Gorgeous 1926 vaudeville-era theater.

  • Old Joliet Prison: Infamous site from The Blues Brothers and full of real history—tours available!

🛠️ 3. Wilmington – Gemini Giant

  • Stop at the Launching Pad Drive-In and see the Gemini Giant, a preserved “Muffler Man” from the space race era.

  • Learn about mid-century pop culture’s role in shaping roadside America.

🕵️ 4. Dwight – Sinclair & Gangster Ties

  • Ambler-Becker Texaco Station (1933): One of the longest-running service stations on Route 66.

  • Historic Downtown Dwight: Includes a train depot and ties to Al Capone, who reportedly visited here.

🏛️ 5. Pontiac – Murals, Museums, and the Mother Road

  • Route 66 Hall of Fame & Museum: Full of personal stories and artifacts.

  • Pontiac Oakland Auto Museum: A treat for classic car lovers.

  • Livingston County War Museum: Excellent local military history resource.

  • Don’t miss the Route 66 murals all over town—they tell the story visually.

🛤️ 6. Atlanta – Giant Paul Bunyan & Clock Tower

  • The Paul Bunyan Hotdog Statue is quirky, but the town has deeper roots.

  • Visit the Atlanta Public Library & Clock Tower (built in 1908).

  • The Downey Building has been around since 1867 and hosted Lincoln as a young lawyer.

🧱 7. Springfield – Lincoln’s Hometown

  • Abraham Lincoln Presidential Library & Museum: A history buff’s dream.

  • Lincoln Home National Historic Site: Tour Lincoln’s actual residence.

  • Old State Capitol: Lincoln served here as a legislator and delivered part of his "House Divided" speech.

  • Cozy Dog Drive-In: Birthplace of the corn dog and classic Route 66 grub.

🌽 8. Litchfield – Drive-In and Downtown

  • Litchfield Museum & Route 66 Welcome Center: Focused on the town’s role in 66 history.

  • Sky View Drive-In (since 1950): One of the last remaining original Route 66 drive-ins.

🕰️ 9. Edwardsville / Mitchell / Chain of Rocks Bridge

  • Cahokia Mounds (nearby): If you want deep history, explore this pre-Columbian Native American city.

  • Old Chain of Rocks Bridge: Historic crossing of the Mississippi River into Missouri, with that iconic bend.

Bonus:

📚 Look for historic Route 66 plaques and restored buildings along the way. Illinois has invested in preserving as much of the original road and its structures as possible.