The fair place to meet is Chicago, IL — the city closest to the midpoint of Kansas City and Milwaukee. From the farther side that’s about 8 hr 39 min of driving.
Recommended midpoint
Chicago, IL
From Kansas City
8 hr 39 min
412 mi to Chicago
From Milwaukee
2 hr 2 min
81 mi to Chicago
Milwaukee has the shorter trip; the split is off by about 6 hr 37 min. The alternatives below can even it out. Kansas City and Milwaukee are about 441 miles apart.
Kansas City and Milwaukee are about 441 miles apart by road. Split the difference and you arrive near Chicago, the city closest to the halfway point between them. That puts roughly 8 hr 39 min of driving on the Kansas City side and 2 hr 2 min on the Milwaukee side — the fairest single meeting point among the cities near the middle.
That's a half-day drive from each side, so Chicago suits an overnight or a weekend rather than a quick coffee — long enough to want a reason to stay, short enough to drive.
If Chicago doesn't have what you're after, Omaha and Indianapolis are also close to the midpoint and worth a look — each keeps the drive reasonably balanced between Kansas City and Milwaukee.
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 →
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 →
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.