The fair place to meet is Chicago, IL — the city closest to the midpoint of Cincinnati and Omaha. From the farther side that’s about 9 hr 3 min of driving.
Recommended midpoint
Chicago, IL
From Cincinnati
5 hr 17 min
252 mi to Chicago
From Omaha
9 hr 3 min
431 mi to Chicago
Cincinnati has the shorter trip; the split is off by about 3 hr 46 min. The alternatives below can even it out. Cincinnati and Omaha are about 621 miles apart.
Cincinnati and Omaha are about 621 miles apart by road. Split the difference and you arrive near Chicago, the city closest to the halfway point between them. That puts roughly 5 hr 17 min of driving on the Cincinnati side and 9 hr 3 min on the Omaha 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, Indianapolis and Milwaukee are also close to the midpoint and worth a look — each keeps the drive reasonably balanced between Cincinnati and Omaha.
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 →
Cincinnati is the most populous city in Hamilton County, Ohio, United States, and its county seat. Read more →
Omaha is the most populous city in the U.S. state of Nebraska. It is located in the Midwestern United States along the Missouri River, about 10 mi (15 km) north of the mouth of the Platte River. 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.