Well, part of the boredom aspect is that between New England and the Midwest, there’s not anything all that striking to see. I mean, there are plenty of interesting places to visit along the way if you wanted to, but nothing spectacular about the terrain. Except for parts of it being flatter than others, it’s not gonna look that different from home.
We did a month-long road trip over 30 years ago - a memory I still treasure. We were living in North Carolina, and didn’t really feel the trip had begun until the third day when we crossed the Colorado state line. And we were in a Mazda 626 loaded with supplies (camping stuff), luggage, food (cooler + non-cooler snacks) and so on so it was a tight squeeze.
We’ve driven from the DC area to the Chicago area several times and it’s a boring, long, shoot-me-now kind of drive - we wind up taking turnpike after turnpike, with associated traffic jams (seldom with any visible cause, mind you). The first time we did it, it was with a 3 year old who decided that cars were no longer an instant “go to sleep NOW” tool… and a 3 month old who screamed the entire drive. It takes us about 12-14 hours if we make very good time, don’t speed TOO blatantly, and barely stop; I’m guessing for you it’d be 18-20 hours, so if you do make the trip, tell your husband you are NOT doing it one day.
The 24-hours-solid sounds pretty painful - that’s brutal. It’s amazing how exhausting it is to just sit in a car. We drive to Florida periodically (about a thousand miles); we always stop about 2/3 of the way there, and we always find the second day feels as long as the first.
Consider some alternatives: Is physical comfort an issue? I’d hate to make a trip like that in our Civic. Our CRV is more tolerable but you could consider renting a roomier car so you have legroom. You could take a train out to, say, Chicago, and get a car there and road-trip just that part of it. With a train you can walk around while you’re on the move, and no need to worry about finding a bathroom or a gas station.
If you do drive, look up every kind of roadside attraction you can. Many will be cheesy as hell but it can be a diversion to stop at a couple of them.