Chicago holiday plus another centre?

[m0therofdragons]

We want to visit my family in milwaukee so we are thinking about flying into Toronto, seeing niagra falls, driving to Chicago over a few days stopping in hotels on the way, a few days in Chicago then up to milwaukee with a week in a house on the lake. Max 3 weeks in total.
Does this sound insane? Anyone have better suggestions? This would be with 3dc who will be 9 and twins almost 6.

You will need to ensure that the rental car company will allow you to take the car into the US from Canada. Also if you drive there, where will you leave the car - in Chicago or Milwaukee?. This part of it needs to be sorted out properly.

I would therefore look at flying into Chicago from Toronto instead of driving there or even starting and ending your trip in Chicago.

I would also look at chains like the Embassy Suites in Chicago as these are ideal for families; the rooms are suite based and thus bigger in size.

Thank you. I'm starting to think we should just focus on the big lakes and chicago.