[wtwo3]

As for all the New York comments. I've lived in Chicago for quite a while now, and just recently went on a short 4 day trip to New York. It's definitely something worth seeing. Yes it's loud and chaotic, but that in itself is a sight to see. Plus with great food options and plenty to see and do, I'd highly recommend checking it out.

I also echo some comments about hiring a car that'll put you in a better position to drive in snow. Definitely look for an AWD, SUV type, and preferably with snow tires. Midwest winters can get very unpredictable. And if you're driving through a lot of Michigan, some of the rural roads off the highway can remain unplowed after a snowstorm.

Also something to consider, if this is a one-way trip through the midwest, car hire prices can skyrocket if you don't return the car back to the same place you hired it. So unless you really want to road trip the midwest United States, you might also consider public transportation options (flying, trains, etc). Those would also be much safer options than driving given the unpredictability of the weather.