No tips for the Canadian side, if you like the Baseball HOF in Cooperstown you might also consider the Basketball HOF in Springfield, or the Football HOF in Canton? I’d like to hit all three someday.
Summer might also be a good time to catch a ball game, lots of stops/options along the way.
Chicago has some fun stuff to do and see with kids; my stomach would love to go back someday.
Good luck, sounds like it’s a great opportunity to make some memories
