The fair place to meet is Oklahoma City, OK — the city closest to the midpoint of Chicago and Tucson. From the farther side that’s about 16 hr 51 min of driving.
Recommended midpoint
Oklahoma City, OK
From Chicago
14 hr 31 min
692 mi to Oklahoma City
From Tucson
16 hr 51 min
803 mi to Oklahoma City
Chicago has the shorter trip; the split is off by about 2 hr 20 min. The alternatives below can even it out. Chicago and Tucson are about 1,443 miles apart.
Chicago and Tucson are about 1,443 miles apart by road. Split the difference and you arrive near Oklahoma City, the city closest to the halfway point between them. That puts roughly 14 hr 31 min of driving on the Chicago side and 16 hr 51 min on the Tucson 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. Oklahoma City still makes a fair, central place for Chicago and Tucson to converge, splitting the travel instead of asking one side to cross the country.
If Oklahoma City doesn't have what you're after, Kansas City and Dallas are also close to the midpoint and worth a look — each keeps the drive reasonably balanced between Chicago and Tucson.
Oklahoma City, often shortened to OKC, is the capital and most populous city in the U.S. state of Oklahoma. It is the 21st-most populous U.S. city and 8th largest in the Southern United States, with a population of 681,054 at the 2020 census. 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 →
Tucson is the county seat of and the most populated city in Pima County, Arizona, United States. 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.