Cheap flights from Connecticut to Caribbean Islands from $74

The month of January is, on average, the cheapest month to fly to Caribbean Islands from Connecticut, with most prices found around $303. The month of May is another great option to travel to Caribbean Islands, with average flight prices from Connecticut averaging around $305.

The cheapest day to depart from Connecticut to Caribbean Islands is on a Sunday. Travelers who choose to depart for Caribbean Islands on a Sunday will often find tickets for as low as $341. If your travel schedule is flexible, try to avoid departing on a Friday because tickets tend to average around $388. These prices are subject to change though, so be sure to set up a Price Alert for flights to Caribbean Islands.

According to our data, the cheapest time of day to fly to Caribbean Islands is in the afternoon. momondo users have found flights departing from Connecticut to Caribbean Islands in the afternoon for as low as $339. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. Try not to purchase tickets at noon because they tend to be around $395. Of course, these prices can vary depending on the time of year and what airport you fly to.

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

There are 2 cabin classes available to choose from on Connecticut to Caribbean Islands flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

No. A direct flight is the cheapest option for a flight between Connecticut to Caribbean Islands.

Delta, United Airlines, and Southwest are the most popular carriers operating from Connecticut to Caribbean Islands

JetBlue, Frontier and American Airlines are the top three most popular airlines that fly to Caribbean Islands from Connecticut according to our data. JetBlue is the first choice among our users, with 52% of people opting to fly with this airline when traveling to Caribbean Islands. Keep in mind that there are 8 different airlines that fly to Caribbean Islands on a routine basis, so you have a few additional options to choose from.

As of March 2026, there are 81 flights per day flying from Connecticut to Caribbean Islands. The most common time of day flights depart is 9:00AM, with 78% of flights taking off at noon.

567 flights are operational weekly from Connecticut to Caribbean Islands as of March 2026. The most popular departure day for this route is Wed, with 20% of flights per week taking off on this day.