Navy Pier (Chicago Start)
Google flags Navy Pier as the symbolic Route 66 starting selfie spot, but the real Mother Road begins a mile west at Adams & Michigan. Treat it as a half-day Chicago kid-stop: 200-ft Centennial Ferris wheel, the free Chicago Children's Museum (Thursday evenings 4-8 PM), and Lake Michigan boat rides. Park here, photograph the actual 'Begin Route 66' sign downtown, then come back for dinner.