I will be flying:
Canada ---> IAD/ORD ---> Tokyo

Which airport: Chicago (ORD) or Washington DC (IAD) is
a) more convenient (ie less walk from gate to gate, friendly staff)
b) more high-tech (ie free wireless internet in the airport - i dont use lounges)
c) has less chance of snow (dont want my flight to get delayed/cancelled)?

Thank you in advance!

Also, how much of a hassle is it to go from Terminal 1 ---> 2 in Chicago Airport? Is it do-able in 3hours (including, getting luggage, going through security etc)?

Also, which airport will give me a higher chance for upgrade?

Sorry to bombard you with questions...
I dont really know if this is the right place to ask these sort of questions either...