Puerto Rico is still on the long road to recovery after Hurricane Maria and tourism numbers are starting to creep back up. Aguadilla, while impacted by the hurricane still sports great beaches.
This is a great deal from Chicago with a bunch of dates to choose from. Just note that this is not a direct route, and you’ll be stopping in Fort Lauderdale. As always with Spirit and low cost carriers, the base fare only comes with a personal item. If you’re unable to travel with only a small bag, this deal will not be as attractive.
There are some great dates on here, including Valentine’s weekend (2/11-2/15). Hopefully one of them works for you!
Note that these prices are accurate as of the time of writing and subject to change.