You have made a great choice! ORD/MDW-BOS is one of the most inexpensive routes on most airlines to/from Boston.
To get to NYC, there's Amtrak ($100 roundtrip per person if booked in advance) and NYC is a short hop away if flying, and that generally costs $150 per person regardless of airline. If JetBlue's promo fare for LGA holds up until April, you can fly BOS-LGA for as little as $61 roundtrip.