1. Start in Chicago – Skydeck at Willis Tower
Kick off your Route 66 journey by stepping onto The Ledge at the Skydeck of Willis Tower (formerly Sears Tower). It’s a glass balcony that extends 4.3 feet from the building at 1,353 feet high—a thrilling start!
2. Route 66 Raceway (Joliet, IL)
If you love speed, check out Route 66 Raceway, which hosts drag racing and other motorsports events.
3. Old Joliet Prison Tour
Take an eerie, self-guided or guided tour through this abandoned prison, famous from The Blues Brothers movie and other legends.
4. Gemini Giant (Wilmington, IL)
A classic Muffler Man statue turned astronaut—perfect for those who love quirky roadside Americana.
5. Exploring the Bridges of Route 66
Kern Bridge (Pontiac, IL) – A historic, iron bridge great for photography.
Old Chain of Rocks Bridge (Madison, IL) – A mile-long bridge crossing the Mississippi River; you can walk or bike it.
6. Pontiac – Route 66 Hall of Fame & Swinging Bridges
Visit the Route 66 Hall of Fame Museum for classic car history.
Try the swinging pedestrian bridges over the Vermilion River.
7. Lincoln’s Ghost Walk & Tomb (Springfield, IL)
Take a nighttime ghost tour in Springfield about Abraham Lincoln’s eerie legends.
Visit Lincoln’s Tomb and try the tradition of rubbing his nose for good luck.
8. World’s Largest Catsup Bottle (Collinsville, IL)
A massive 170-foot water tower shaped like a ketchup bottle—it’s bizarre but worth a stop for adventure seekers.
9. Cahokia Mounds State Historic Site
A UNESCO World Heritage Site, this ancient city has 120+ mounds built by Native Americans over 1,000 years ago. Climb Monks Mound, the largest prehistoric earthwork in the Americas.
10. Chain of Rocks Bridge & Mississippi River Overlook (Madison, IL)
Walk or bike this historic bridge, which once carried Route 66 traffic. The unique 22-degree turn in the middle is a cool architectural quirk.