Answer: The obvious answer is 5 miles.The not-so-obvious part is it depends on where he is when he starts. If he is on the equator, he is five miles from his point of origin. If his starting point was the south pole, and he drives five miles north, then west, then south, he will arrive back at his starting point. Before you disagree, consider that he is driving on a sphere not a flat plain.
Answer: It is 1,671 miles according to Google Maps, or you could take a route that is a bit longer, but would bypass more major cities than you would have to go through with the shorter route (at least from Charlotte to the Chicagoland area). This route is, in fact just under 80 miles longer, and is approximately 1,755 miles taking this route:
Take I-77 NORTH, from Charlotte, to I-80 OHIO TURNPIKE (toll road) at EXIT 146 in OHIO; follow signs on the exit ramp to I-80 WEST to TOLEDO.
Take I-80 WEST, across the OHIO TURNPIKE, and across the Indiana TOLL ROAD (EXIT 21 off the Indiana Toll Road to continue on I-80), into ILLINOIS, where you will exit onto I-294 TOLLWAY - NORTH to WISCONSIN.
Take I-294 NORTH, on the TOLLWAY, to I-90 TOLLWAY - WEST to ROCKFORD.
Take I-90 WEST to I-94 WEST to ST. PAUL at EXIT 45 in WISCONSIN. To bypass ST. PAUL/MINNEAPOLIS, take I-694 NORTH (& WEST) (EXIT 249 off I-94 in MINNESOTA to get onto I-694 NORTH ; EXIT 27 off I-694 WEST to continue WEST on I-94 towards ST. CLOUD).
Continue on I-94 WEST across to EXIT 256 in NORTH DAKOTA, which is the U.S. 52 WEST - TRUCK ROUTE around Jamestown. Follow signs off the exit ramp to U.S. 52 WEST.
Answer: The driving distance is about 200-210 miles. Since there is sometimes more than one route, including back roads, this is an approximate but accurate distance. It is based on the most well-known routes between these two locations.