Cheap flights from Hartford to Caribbean from $108

In general, May is the cheapest month to fly from Hartford to Caribbean. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $378. If you don’t want to visit Caribbean in May, then you should wait until January to fly from Hartford, when ticket prices are also cheap, with an average price of $395.

The cheapest day to depart from Hartford to Caribbean is on a Tuesday when prices can be found for as low as $352. If your travel schedule is flexible, try to avoid departing on a Thursday because tickets tend to average around $391. These prices are subject to change though, so be sure to set up a Price Alert for flights to Caribbean.

At noon is the cheapest time of day to fly from Hartford to Caribbean when you can find flight prices for as low as $336. Flying to Caribbean at noon is an ideal time because this is during off-peak travel hours. Flights in the morning are often more expensive with an average ticket price of $403.

Fly from Hartford Bradley Intl to San Juan Luis Munoz Marin Intl for the best Hartford Bradley Intl - Caribbean flight prices

You are more likely to see cheaper flights to Caribbean from Hartford when booking weeks ahead of your departure date. In general, you can expect to find flights to Caribbean for around $359 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Caribbean from Hartford for as low as $325 on momondo.

There are 4 cabin classes available to choose from on Hartford to Caribbean flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Southwest, Delta, and JetBlue are the most popular carriers operating from Hartford Bradley Intl to Caribbean

JetBlue, American Airlines and Avelo Airlines are the top three most popular airlines that fly to Caribbean from Hartford according to our data. JetBlue is the first choice among our users, with 72% of people opting to fly with this airline when traveling to Caribbean. Keep in mind that there are 7 different airlines that fly to Caribbean on a routine basis, so you have a few additional options to choose from.

1 flights are operational daily from Hartford to Caribbean as of September 2026. The most popular departure time for this route is 2:00PM, with 70% of flights per day taking off in the afternoon.

The number of flights available between Hartford and Caribbean is 10 per week as of September 2026. The most frequent departure day is Mon, with 20% of weekly flights leaving on this day.