We went earlier this year, so here's my experience:
- we flew out of Wpg to Montreal, and then from Montreal to Newark airport in NJ. This eliminated any delays and all flights were on time. I would definitely recommend this route - avoid Toronto at all costs as flights to NYC from there always get delayed. Same goes for La Guardia and JFK airports in NYC - avoid if possible. If you do go to Newark Airport as your destination - there is a bus shuttle service (called Newark Airport Express - you can buy tickets in advance on their website) that takes you from the airport to Manhattan (3 different stops, very convenient) - by far the best and cheapest way to get FROM/TO the Airport (was around $16 CAD/person - one way, if I remember correctly.)
Travelling in the city - if you've never used subway before, it may be a bit confusing, especially because it's NYC (I have been to quite a few large cities with subway) and it still took a day or so to get it all worked out. Taxi is probably the best and fastest way to travel in Manhattan over short distances, fairly cheap too.
We stayed in hotel - The Court (corner of Lexington Ave and E 39th St), managed to get a good deal - 4 nights for $650 USD. Not the top of the line hotel, can tell it's a bit older building, but nicely renovated and clean. Happy with the stay, all-in-all. You could also try and look into B&B - check out AirBnB and see what's available.
As to places to eat - a must go is Italian restaurant "Carmines" near Times Square - enormous portions of great food, and cheap too! Great place!
Things to see: Central Park, Museum of Natural History, go to 86th or 101st floor observatory of Empire State Building - breathtaking views. Visit 9/11 memorial, Brooklyn Bridge and the High Line. Take a boat tour around the island. NYC is a fantastic city with soooo much to do and see, make the most of it! Loved every minute of it, will definitely be back!