There’s something almost magical about standing at the very beginning of Route 66, right at Adams Street and Michigan Avenue. This is where generations of travelers once pressed the accelerator and set out on an adventure across America. The “Begin Route 66” sign may be modest, but it carries the weight of decades of stories—families, dreamers, and wanderers all leaving the city behind for the open road. Take a moment here. Pause. Snap a photo. Feel the energy of Chicago around you and imagine the long stretch of road ahead, waiting to be discovered. This is your starting line, and every mile from here is part of a journey steeped in history, culture, and Americana.