North East Loop Start/Finish in Chicago

Hi there, I'm looking at doing a road trip starting and finishing in Chicago with approximately the following stops.

Chicago
Detroit
Toronto
Ottowa
Montreal
Boston
New York
Philly
Washington DC
Chicago

Now I realise that there is a large amount of road between a few of these stops and that's why I come to you, dear forum. Could you recommend some good places to stop for maybe one night or so on the longer portions of the road. Would be looking for probably something off the beaten track a little, towns with good character I guess you'd say.

Also, how difficult is it to hire a car under the age of 25? I am 22 and will have an international drivers permit but have been told I wouldn't be able to hire at all. Is this true? Or will they just slap on an under 25 surcharge? Also, If it is actually possible, do you know what the better car hire companies are in the states?

One last thing, is it too broad a trip to even ask how much time you would allow for such a road trip? I'm thinking probably close to a month.

Thanks so much for your help!

Luke

Welcome to the RTA Forum!

You should be able to rent a car, but you will certainly have a surcharge that will run about $25 per day per driver. The other issue may be getting permission to cross the border. Either one of those shouldn't be a problem, but trying to do both could potentially be an issue. You'll really just have to shop around, because there is no "better" company for every situation, and that's especially true when you've got a lot of fairly unusual specifics like you do.