Vacation ideas? Montreal, New Brunswick, Nova Scotia, Chicago

[Ser Clegane]

Vacation time is coming soon and I would like again to pick the brains of our community for some recommendations for the trip.

In June Mrs Clegane and me will fly to Montreal and spend a couple of days there. The plan is then to go by car from there through New Brunswick and Nova Scotia to Halifax,
From there we will fly to Chicago to spend a couple of days there before going back home.

Any recommendations what to visit at these places? For the trip from Montreal to Halifax we have 11 days, so enough time for some stops (we did the route Toronto-Montreal before and also went to Quebec City and Gaspé at that time, so that part is "out of scope")
For Montreal and Chicago ideas for places to eat at would be highly welcome (this is the stuff you typically to not find in a travel guide).

Thanks in advance for any ideas!