Illinois
Ok, you are ready to start your trip, and Illinios has a lot to see and do.You will find getting out of Chicago surprisingly easy. In under an hour, you will be through Al Capone's haunts in Cicero, and on the way you'll see Cindy Lou's Motel, Henry's Drive-In, the Castle Car Wash and other classic Route 66 sites.
All of a sudden you'll find yourself in Joliet to see the Rialto Square Theater, Joliet Prison and sculptures of Jake and Elwood Blues atop the Rich & Creamy ice cream stand.
After that, you'll be on rural roads with the interstate hiway system only an afterthought. You'll see The Gemini Giant, the Bunyon Statue with his giant hot dog and the largest covered wagon in the world with a giant Abe Lincoln aboard.
There are small towns with proudly restored gas stations from the 1930s, some of them serving as visitors centers or museums. There roadhouses that were frequented by Al Capone and many restored motels with classic neon signs. There is a lot of old road to follow with many bridges from the 1920s and 30s. There even are some old brick portions of Route 66.
In Springfield, you can visit Abe Lincoln's home, office, presidential library and tomb.
You also will find Springfield to be a super biker town with many biker bars along the Springfield Mile and many motorcycle clubs.
Twelve Illinois towns starting th Joliet and ending in Towanda participate in the Route 66 Red Carpet Corridor. Each of the participating towns puts on an annual festival, many of which feature antique cars and motorcycles.
Route 66 through Illinois is surprisingly rural. Take it slowly and enjoy!
Click here, to see the first town in Illinois, Chicago.