The fair place to meet is Columbus, OH — the city closest to the midpoint of Milwaukee and Raleigh. From the farther side that’s about 7 hr 51 min of driving.
Recommended midpoint
Columbus, OH
From Milwaukee
6 hr 57 min
331 mi to Columbus
From Raleigh
7 hr 51 min
374 mi to Columbus
Milwaukee has the shorter trip; the split is off by about 54 min. The alternatives below can even it out. Milwaukee and Raleigh are about 704 miles apart.
Milwaukee and Raleigh are about 704 miles apart by road. Split the difference and you arrive near Columbus, the city closest to the halfway point between them. That puts roughly 6 hr 57 min of driving on the Milwaukee side and 7 hr 51 min on the Raleigh 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 Indianapolis are also close to the midpoint and worth a look — each keeps the drive reasonably balanced between Milwaukee and Raleigh.
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 →
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 →
Raleigh is the capital city of the U.S. state of North Carolina. It is the second-most populous city in the state, tenth most populous city in the Southeast, the largest city in the Research Triangle area, and the 39th-most populous city in the U.S. 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.