Where it all begins—or ends, depending on where you call home. Route 66, aka the "Main Street of America," opened in 1926 and runs from Chicago, Illinois, to Santa Monica, California. Just outside of Grant Park, facing west on Adams Street in Chicago, you'll find the original Begin Historic Illinois Route 66 sign. The end sign is just a block away, at Jackson Boulevard and South Michigan Avenue. Like generations before you, be sure to grab a bite at Lou Mitchell's, a diner established in 1923 that was put on the National Register of Historic Places in 2006.