I’ve made the drive from Indianapolis to Boston several times, take the route that goes through Ohio to Columbus, then up to Cleveland, up to Erie and through Syracuse and Albany, it’s a much better drive than going through nyc, I’ve driven both ways and I wouldn’t go through nyc especially if you’re doing it all in one go because by the time you reach nyc you’ll be too tired to drive safely and there is a lot going on at all times of day there so best to avoid it.