We're finally able to go look at colleges in these three cities, but I am hopelessly confused as to how to do it.

We will fly from Honolulu to Chicago and spend one day looking at 2 schools there.
Next we need to go to Boston for 2 days, then finally NYC for about 3 days.

Is it best to just fly into each city or is there a better way (Maybe fly Chicago to NYC then do a train NYC-Boston & back?)

Is there any reason to choose one airport over another in these cities?

And last, if we wanted to squeeze in DC, agian is the train or plane teh best method?

We'll be attemptimg this March 16 (night flight) to March 24.

Thanks for your help!

I would fly from Chicago to Boston and then train/bus to NYC. There are many discount busses from Boston to NYC for $15 per person and take 3-4 hours. www.chinatown-bus.com From NYC to DC www.easternshuttle.com It can just as fast to bus sometimes as getting to an airport and checking in etc.

Why no earth would you fly from Chicago to NYC if our actual destination was Boston? Fly to Boston, then take ground transport to NYC -- as kybourbon pointed out, the time commitment is about the same, and it's a lot less hassle and expense. Greyhound and Fung Wah buses are reliable and economical; both leave from South Station in Boston.

If you try to add DC, then I would fly from Chicago to NYC, bus to Boston, then fly Boston to DC -- this will spend the smallest amount of your precious time on transportation. Or, if you are definitely flying home from NYC, then fly Chicago - DC - Boston, then bus to NYC.

Chicago-Boston can be done cheaply, around $200. You'll get the best fares out of O'Hare airport, but both of Chicago's airports have train connections to downtown; the trip takes about 40 minutes.

Which colleges are you visiting?

I agree with the advice above, however, don't limit your search for Boston-Chicago airfare to O'Hare. I just flew for $174 roundtrip from Midway a couple months back and both airports are equally accessible from the city.