You are probably right odyssey06 , it might be better to stay on either USA side or the Canadian side but not both. My son who was 26 did San Francisco, Los Angles and Vegas ourselves four years ago, four days in each and it was great. We are both doing this trip too but am not sure how many days is enough in say Boston or Washington or Chicago . Perhaps leave Canada for another time or with the Travel Dept or some other tour group. Would you say one day in Washington is enough ?
I suppose it depends on whether you think you will be back to North America soon, if so I think just pick a country and leave the other cities for a coach tour.
Chicago to the east coast cities is a considerable distance... Montreal, Quebec, Ottawa, Toronto\Niagara is a nice chain; as is Boston, New York, Philadelphia, Washington.
There's probably more variety between the Canadian cities, and if ye haven't been to Canada before, nice to tick that box.
I liked visiting Independence Hall and the Liberty Bell in Philadelphia.
It depends on what kind of holiday you are interested in, if you want to see the famous monuments and museums then you should allow more time in Washington.
If you are more interested in seeing the sights in the afternoon & kicking back in the evening somewhere relaxed with a few beers, then Boston is better.
Try to avoid giving yourself a tight schedule such that you are in a different hotel every night. On the coach tours I was ok if it was 2 nights here, 2 night there, or 1-4-1, but a sequence of one nighters is a bit much.
Might be nice to include a stop somewhere 'mid-sized', so not a famous metropolis, somewhere random like Atlantic City!