The fair place to meet is Denver, CO — the city closest to the midpoint of Los Angeles and Milwaukee. From the farther side that’s about 19 hr 8 min of driving.
Recommended midpoint
Denver, CO
From Los Angeles
17 hr 24 min
830 mi to Denver
From Milwaukee
19 hr 8 min
913 mi to Denver
Los Angeles has the shorter trip; the split is off by about 1 hr 44 min. The alternatives below can even it out. Los Angeles and Milwaukee are about 1,741 miles apart.
Los Angeles and Milwaukee are about 1,741 miles apart by road. Split the difference and you arrive near Denver, the city closest to the halfway point between them. That puts roughly 17 hr 24 min of driving on the Los Angeles side and 19 hr 8 min on the Milwaukee 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. Denver still makes a fair, central place for Los Angeles and Milwaukee to converge, splitting the travel instead of asking one side to cross the country.
If Denver doesn't have what you're after, Albuquerque and Oklahoma City are also close to the midpoint and worth a look — each keeps the drive reasonably balanced between Los Angeles and Milwaukee.
Denver is the capital and most populous city of the U.S. state of Colorado. Officially a consolidated city and county, it is located in the South Platte River valley on the western edge of the High Plains, and is just east of the Front Range of the Rocky… Read more →
Los Angeles (LA) is the most populous city in the U.S. state of California, and the commercial, financial, and cultural center of Southern California. 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.