Keep in mind that Jamaica customs will pull you aside for health screening if you’ve been to another country within the last 6 months. However, they then let you cut the entire line which can be pretty long.
Gogo offers in-flight internet access for $49.95/monthly unlimited on all Gogo equipped flights. Boingo is terrific for land hotspots. For $9.99/monthly, you get unlimited usage and they’ve made it easier for you to access Gogo through the service. However, you’ll be charged according to length of flight — full flights are usually $21.95.