We're tentatively looking at a ~2 week adventure to Chicago, NYC, and possibly Boston following Columbus Day.

This Monday would work better for me.

Is that a problem? :D

I assume you're flying from Chicago to NYC? They're not very close together you know...

Yes, the plan was to fly (the cities were not chosen for proximity but simply because they were the cities we wanted to visit).

But it is a pretty nice road trip, particularly if it is early (or late) summer and you go up north through Canada.

My drive from Chicago, through Michigan, into Canada, crossing back over at Niagara Falls, side tripping to Cooperstown for a visit to the Baseball Hall of Fame, and then on to New York City (which we bypassed but drove close enough to to see the Statue of Liberty on our way to Boston) was a very nice drive. Except for the monster mosquitoes at an uncivilized campground (which was beautiful at dawn but horrible through the night of being consumed) somewhere in upstate New York.

A long road trip is in the cards one of these days, probably involving stops at baseball stadiums along the way. But seeing 2 major cities in under 2 weeks leaves little travel time so it will have to wait until another year.

Yes, but as GD said, given the 2 week time frame, there's no time left to explore Chicago and NYC.

Alex, you visited my stomping grounds! Sorry about the mosquitoes.