The fair place to meet is Chicago, IL — the city closest to the midpoint of Cleveland and Omaha. From the farther side that’s about 9 hr 3 min of driving.
Recommended midpoint
Chicago, IL
From Cleveland
6 hr 27 min
307 mi to Chicago
From Omaha
9 hr 3 min
431 mi to Chicago
Cleveland has the shorter trip; the split is off by about 2 hr 36 min. The alternatives below can even it out. Cleveland and Omaha are about 738 miles apart.
Cleveland and Omaha are about 738 miles apart by road. Split the difference and you arrive near Chicago, the city closest to the halfway point between them. That puts roughly 6 hr 27 min of driving on the Cleveland 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, Milwaukee and Indianapolis are also close to the midpoint and worth a look — each keeps the drive reasonably balanced between Cleveland 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 →
Cleveland is a city in the U.S. state of Ohio and the county seat of Cuyahoga County. Located along the southern shore of Lake Erie, it is situated across the lake from Ontario, Canada, and is approximately 60 miles west of the Ohio–Pennsylvania state line. 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.