The problem is that IU is a good 1+ to the Indy airport, and the Indy itself is not a massive hub. It's probably easiest just to get to Chicago because you can just drive. It's about 4 hours, which is not a nice drive, but certainly doable for weekend trips.
You're going to have to fly with the other two, and given that I'd reckon its slightly easier to get into NY because there will be more flights headed that way. But either way, I don't think you could do the weekend trip thing with either. You're probably looking at a half to full day travel.
It will be especially hard if you plan on going the other way, from NY or Philly to Bloomington. Then you'd have to not only get ground transportation on the way there, but you'd probably need to a rental as well. There are shuttles, but I wouldn't rely on those.
This is pretty much right on. You can make it to the airport in an hour as long as you drive aggressively and you have a good route.
Chicago is a straight 4 hour drive that is pretty easy.
For NY and Philly: you'll have more flight options for NYC (airlines and airports), but it won't be cheaper or shorter than Philly. For Philly, its pretty much just US Air flight, but it is never too expensive. Your total time in transit may actually be better for PHL depending on how far you would live in NYC from JFK, LGA, or EWR.
If you are the one coming in to Bloomington, then that would mean that someone would have to pick you up from the airport (whereas if you were in Chicago, you could presumably drive directly to Bloomington). There is a shuttle, but it takes way too long and doesn't run often enough.
That pain when it comes to the airport would make me favor Chicago.
It is one thing for someone who goes to school here to drive to the airport (it only adds an hour to the trip, and airport security is always very quick, so I don't mind the tradeoff). But for people coming in to Bloomington, it will be tougher.
Future 1L here - I am looking for the best gym that's close to campus, I want to be able to work out between/after/before classes without having to drive anywhere. Suggestions?
The HPER is a 10 minute walk and is not what I would call "the best gym." The SRSC is a 25 minute walk (or 5 minute drive) and is the better of the 2 IU gyms.
There is definitely a private gym on College Ave, but that wouldn't be a quicker walk than the HPER.
I drive to the SRSC and just accept it as one the few places that I drive to in this town.