You'll adore Pontiac. The Route 66 Association of Illinois Hall of Fame and Museum is located here and it's an incredible repository for thousands of pieces of historic memorabilia from the glory days of the Mother Road. Mooch through a treasure trove full of kitsch and nostalgia AND great photo ops!
Pontiac is also famous for its Murals on Main Street. The 23 outdoor murals depict the city's varied local history. Most of the murals can be seen by car, but grab a mural map from the museum and do a self guided walking tour. Start with the largest mural, the Route 66 shield, found right on the back of the Hall of Fame and Museum. At its base are bricks from the original Route 66 alignment that ran through Pontiac.