Travel from Chicago to Nova Scotia

You should have no problem. I'd take I-90 to 295 to 495 to 95 to Bangor. Then take 9 to rt 1 in Canada.

There is now a ferry that goes from Portland to Yarmouth but it's $$$.

Not to differ - but - I-90 to I-495 in MA will get you to I-95 north of Boston. Then it turns onto I-95 in NH for a short stretch, then it's up to you either stay on 95 or take I-295 in Portland, 295 is 12 miles shorter. Back onto I-95 to Bangor and then I-395 for a couple of miles to catch rte.9 to rte. 1 to Calais for the crossing into Canada. If you have not yet purchased a "Doers & Dreamers Travel Guide", I highly recommend you pick one up at tourist info as you enter the province of Nova Scotia. This is a beautiful trip, so drive safely and enjoy.

you might want to plan it to miss boston beltway rush hour
for a smooth sail.
Donna...did that trip last year

Just a suggestion: Have you considered going up through Canada? You can cross into Canada in either Detroit or Port Huron, MI and then catch 401 through Toronto. We've only crossed at Port Huron as we shy away from Detroit if at all possible. We took this route back in 2009 on our way to Bar Harbor, ME. Toronto is a bit busy, but not as bad as Cleveland or Boston, etc.

Thanks to all for their replies.