The fair place to meet is Kansas City, MO — the city closest to the midpoint of Dallas and Milwaukee. From the farther side that’s about 9 hr 31 min of driving.
Recommended midpoint
Kansas City, MO
From Dallas
9 hr 31 min
454 mi to Kansas City
From Milwaukee
9 hr 15 min
441 mi to Kansas City
That’s an even split — both sides drive within 16 min of each other. Dallas and Milwaukee are about 858 miles apart.
Dallas and Milwaukee are about 858 miles apart by road. Split the difference and you arrive near Kansas City, the city closest to the halfway point between them. That splits the trip almost evenly — about 9 hr 31 min from Dallas and 9 hr 15 min from Milwaukee.
Over this distance most people will fly rather than drive the whole way. Kansas City still makes a fair, central place for Dallas and Milwaukee 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 Omaha are also close to the midpoint and worth a look — each keeps the drive reasonably balanced between Dallas and Milwaukee.
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 →
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 →
Milwaukee is the most populous city in the U.S. state of Wisconsin. It is located on the western shore of Lake Michigan at the confluence of the Milwaukee, Menomonee, and Kinnickinnic Rivers. 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.