161.5 miles: 3 hours, 50 minutes
It’s all about the open road on this Route 66 journey across Illinois. Along the way, there are plenty of opportunities for photos (with a giant pink elephant, anyone?) and fuel (a stop at Ariston Cafe has been a Route 66 tradition since 1924). Retro gas stations, faded neon signs, drive-in theaters and Abe Lincoln’s hometown—the Americana on this trip can’t be beat.