The fair place to meet is Columbus, OH — the city closest to the midpoint of Chicago and Richmond. From the farther side that’s about 7 hr 12 min of driving.
Recommended midpoint
Columbus, OH
From Chicago
5 hr 47 min
276 mi to Columbus
From Richmond
7 hr 12 min
343 mi to Columbus
Chicago has the shorter trip; the split is off by about 1 hr 25 min. The alternatives below can even it out. Chicago and Richmond are about 619 miles apart.
Chicago and Richmond are about 619 miles apart by road. Split the difference and you arrive near Columbus, the city closest to the halfway point between them. That puts roughly 5 hr 47 min of driving on the Chicago side and 7 hr 12 min on the Richmond side — the fairest single meeting point among the cities near the middle.
That's a half-day drive from each side, so Columbus suits an overnight or a weekend rather than a quick coffee — long enough to want a reason to stay, short enough to drive.
If Columbus doesn't have what you're after, Cincinnati and Cleveland are also close to the midpoint and worth a look — each keeps the drive reasonably balanced between Chicago and Richmond.
Columbus is the capital and most populous city of the U.S. state of Ohio. With a population of 905,748 at the 2020 census, it is the 14th-most populous city in the U.S., second-most populous city in the Midwest, and third-most populous U.S. state capital. Read more →
Chicago is the most populous city in the U.S. state of Illinois and in the Midwestern United States. Located on the western shore of Lake Michigan, it is the third-most populous city in the United States, with a population of 2.74 million at the 2020 census. Read more →
Richmond is the capital city of the U.S. state of Virginia. Incorporated in 1742, Richmond has been an independent city since 1871. It is the fourth-most populous city in Virginia, with a population of 226,610 at the 2020 census. Read more →
City descriptions adapted from Wikipedia (CC BY-SA); photos via Wikimedia Commons, credited above.
Estimates use straight-line distance and typical road speeds; real drive times vary with route and traffic.