Taking I-90 between upstate New York and Cleveland carries a high risk of lake effect snow, as does I-94/I-80 in the Chicago area. If I were making this trip, I'd look at the following first:

Take your route of choice to Toronto.
401/402 to Sarnia
I-69 to Indianapolis
I-70 to St. Louis
I-44/I-40 to Albuquerque
I-25 to Hatch
NM-26 to Deming
I-10 to Tucson