What is the distance between Winchester VA and Chicago?

Answer 1

665 miles taking this route:

1. Take I-81 NORTH (towards MARTINSBURG), from Winchester, to I-70 WEST to HANCOCK at EXIT 4B, near Hagerstown, Maryland.
2. Take I-70 WEST to I-76 Pennsylvania TURNPIKE (toll road) - WEST to PITTSBURGH, at BREEZEWOOD, PENNSYLVANIA.
3. Continue on I-76 WEST, on the PENNSYLVANIA TURNPIKE, to OHIO, where I-76 WEST continues as the OHIO TURNPIKE (toll).
4. Continue on the OHIO TURNPIKE (toll) - WEST, on I-76, and then later on I-80, and then I-80/I-90, to Indiana, where I-80/I-90 continue as the Indiana TOLL ROAD.
5. Continue on the TOLL ROAD - WEST, on I-80/I-90 to CHICAGO, via either I-90 SKYWAY or via I-94 WEST.