Good luck, vrboone. Here are a few other tips that you probably already know, but just in case. Make sure you're carry-on bag(s) fits in the overhead bins. Don't let them 'gate-check' it for you. That takes additional time. Also, see if you can find out in advance what terminal and gate you are landing at from Chicago, and which ones are you departing from for St. Maarten. If the terminals are the same or right next to one another that would be a big advantage. Don't quote me on this, but I believe AA uses Concourse D for their international flights. So, if your flight from Chicago gets off in Concourse B or C you can walk quickly over to Concourse D. Hope it all goes well for you!