Hi Andrea,

I'm not nuts about you taking the subway by yourself from subway stations near Columbia. That's something I would not do. You probably will be fine but with your luggage and such, you won't be able to move quickly if you absolutely need to do so.

For me, safety is first. If you can spare the $45 plus tip, take a taxi to JFK. If not, take a taxi to Penn Station and take the LIRR to Jamaica to the Airtrain. If that's too pricey, take a bus but keep in mind, that might take a bit of time as I'm not sure if there are limiteds at that hour. I just looked up some trains for you from Penn: there's a 5:11, 5:26, 5:47, 6:07, 6:36, 6:47, 6:58, 7:10, 7:22, you get the idea.

Go to Jamaica's Airtrain over Howard Beach.

You've picked a great time to travel. Hope this helps. PM me if you'd like.