Chicago, Illinois, is the eastern terminus of the Mother Road-depending on which way you travel, you will either start or end your trip across from Grant Park and Lake Michigan. After leaving the Windy City, the road takes you southwest through rural Midwestern towns full of classic motel neon, vintage filling stations, roadside giants, and historic bridges until you hit the Mississippi River and East St. The stretch of Route 66 from Chicago to St. Louis is home to aluminum-and-chrome diners, historic, family-owned cafes, bizarre attractions, and other reminders of the route’s charming past. You’ll also see plenty of cornfields and flat prairie land between the bustling cities and sleepy towns along this first leg. There are nearly 300 miles of Route 66 in Illinois. The state is also home to many of the country’s most famous Muffler Men, those fiberglass titans of retro roadside kitsch. A lot of the old route has been gobbled up by modern highways, in particular I-55, but there’s still plenty of neon, fiberglass, and chrome to keep any roadtripper happy. Traditionally, travelers begin their journey southwest near the shores of Lake Michigan, not spending too much time in Chicago. The Kansas section of Route 66 is short but sweet, and manages to pack in several must-see stops in a little under 14 miles (13.2 to be exact).
