May 1, 2009, through Labor Day, American Eagle will add 109 weekly flights from San Juan to eight Caribbean destinations. These flights were cut in half last year due to higher fuel prices and a floundering economy.

The new schedule from San Juan looks like this:
- 3 daily flights to St. Maarten, up from 1
- 7 daily flights to Tortola, St. Croix and St. Thomas, up from 3
- 1 daily flight to Guadeloupe, up from 4 a week
- 1 daily flight to Martinique, up from 3 a week
- 1 daily flight to Trinidad, up from 4 a week
- 4 weekly flights to Grenada, up from 3