[Helena]

You’ll need to book early for that route. The best you can do NOW is find something on points to ATL, FLL, Tampa, and Miami and then pay cash from there to GCM on Cayman Airways, JetBlue, AA or Delta

[Vernon]

I did JetBlue from JFK to Grand Cayman last year and it was direct and super easy. I also did Southwest to Fort Lauderdale one year and stayed in Fort Lauderdale and then did another Southwest direct to Caymans. I’ve also done American but that was from Pittsburgh. We’ve been a handful of times. Feel free to message me

[Violette]

I used to work for a company that had offices in Grand Cayman. Flying JetBlue there was super easy

[Agustina]

If you could travel anytime in Feb, AA has flights as low as 8k, but if you have to travel that one weekend that is President’s Day, it’s going to be pricey. However, there is a late flight out of LGA on Thursday, Feb 15 for 25k.

I’m sure you know the rule, but try never to be locked into dates and destinations and booking late on a popular weekend. That never ends well.

[Aubree]

My sisters-in-law are both teachers (bless you all lol) and we’re all trying to get to SJU for that weekend as well. Suggest you set price alerts on Google Flights, and consider booking 2 separate one ways vs a traditional round trip. Allows you to pick different carriers.

[Edy]

We are going to SXM in January. We are flying Southwest to Miami, staying overnight, then flying AA (using BA Avios) to SXM. May want to consider looking at different positioning flights and different airlines – similar to getting to Europe.

[Matilde]

Unfortunately my advice would be to book early if it’s a peak travel time like Jan/Feb to the Caribbean.

I’d also check out AA, who anecdotally has had pretty decent award prices to the Caribbean.

We’re going to Grand Cayman in January at a pretty peak time and doing a cash direct flight from JetBlue O/W and a cheap award with a stop on AA coming back (10k AA + some taxes)

[Clay]

SkyMiles from Toronto. Flew my mom for 15k nonstop