The fair place to meet is Kansas City, MO — the city closest to the midpoint of Chicago and Dallas. From the farther side that’s about 9 hr 31 min of driving.
Recommended midpoint
Kansas City, MO
From Chicago
8 hr 39 min
412 mi to Kansas City
From Dallas
9 hr 31 min
454 mi to Kansas City
Chicago has the shorter trip; the split is off by about 52 min. The alternatives below can even it out. Chicago and Dallas are about 805 miles apart.
Chicago and Dallas are about 805 miles apart by road. Split the difference and you arrive near Kansas City, the city closest to the halfway point between them. That puts roughly 8 hr 39 min of driving on the Chicago side and 9 hr 31 min on the Dallas side — the fairest single meeting point among the cities near the middle.
Over this distance most people will fly rather than drive the whole way. Kansas City still makes a fair, central place for Chicago and Dallas to converge, splitting the travel instead of asking one side to cross the country.
If Kansas City doesn't have what you're after, Memphis and Nashville are also close to the midpoint and worth a look — each keeps the drive reasonably balanced between Chicago and Dallas.
Kansas City, abbreviated KC or KCMO, is the largest city in the U.S. state of Missouri by both population and area. It is located on the Missouri River at its confluence with the Kansas River, within Jackson, Clay, Platte and Cass counties. 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 →
Dallas is a city in the U.S. state of Texas. Located in the state's northern region, it is the ninth-most populous city in the United States and third-most populous city in Texas, with a population of 1.3 million 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.