Chicago to Bangor Maine

Going to visit a friend in Maine with my 2 teenage daughters. We will only have a week. Want to get most out of our week. Plan to stop in Niagra to see the falls then get back on road. Would like to do whale watching. Thinking of spending part of day near Boston to do this and see Plymouth Rock.
Then head up to Maine to spend a few days with my friend. Thinking of Fairfield Inn in Bangor. Plan to head to Bar Harbor for day trip too.
On way home thinking of different route to stop and see something different. Suggestions? I know it will be a whirlwind!

Hi, and Welcome to the Great American Roadtrip Forum.

At 1200 miles, this is going to be two long days on the road each way without any significant stops, other than the essentials. Visiting Niagara, Boston and whale watching, and a day trip while in Bangor, is going to leave you precious little time to spend with your friend.

As an alternative route on the way back you could head through Ontario to Sarnia, assuming your passports are in order.

Lifey

The shortest (in terms of time) possible route between Chicago and Bangor, is just I-90/I-95 in essence, and would take a little over two days one way without any major stops. Niagara Falls and Boston (Plymouth is actually a good bit south of Boston) would both add just a few miles, but also a few hours, to get to from that main route. The shortest (in terms of mileage) route would be, very roughly, US-2 into Canada, ON-401 over the tops of Lakes Ontario and Erie through Toronto, then I-69/I-94 from Sarnia ON to Chicago. But that alternative adds considerably to the time needed to drive and as Lifey points out requires that all your passports be in order.

The long and the short of it is that you need to budget 4½ to 5 days of just driving to make a round trip to Bangor which doesn't leave a whole lot of time for sightseeing along the way or to spend with your friends once you get there. This is particularly true given the two stops that you've indicated you'd like to make. Both Niagara and Boston require a considerable amount of time just to get into and out of, and then you have to spend enough time there to make the detour worth the effort.

However, if you could make use of both weekends and make this a nine day trip, then all sorts of opportunities open up, both along your route and in New England in general.
Getting the most out of your week doesn't necessarily mean getting to the most places in the least amount of time, but instead should mean making the best memories for your daughter's lifetimes. And that takes time.

AZBuck