Hartford and Omaha are about 1,200 miles apart by road. Split the difference and you arrive near Detroit, the city closest to the halfway point between them. That puts roughly 11 hr 11 min of driving on the Hartford side and 14 hr on the Omaha 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. Detroit still makes a fair, central place for Hartford and Omaha to converge, splitting the travel instead of asking one side to cross the country.
If Detroit doesn't have what you're after, Columbus and Cleveland are also close to the midpoint and worth a look — each keeps the drive reasonably balanced between Hartford and Omaha.
City descriptions adapted from Wikipedia (CC BY-SA); photos via Wikimedia Commons, credited above.