Cheap flights from Connecticut to Caribbean from $108

In general, May is the cheapest month to fly from Connecticut to Caribbean. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $377. If you don’t want to visit Caribbean in May, then you should wait until January to fly from Connecticut, when ticket prices are also cheap, with an average price of $390.

The cheapest day to depart from Connecticut 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 Connecticut 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 Tweed-New Haven to San Juan Luis Munoz Marin Intl for the best Connecticut - Caribbean flight prices

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

You could potentially save up to 10% on your flight if you consider stops on a Connecticut to Caribbean flight.

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

JetBlue, Frontier and American Airlines are the top three most popular airlines that fly to Caribbean from Connecticut according to our data. JetBlue is the first choice among our users, with 46% 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.

As of September 2026, 1 flights take off from Connecticut and land in Caribbean each day. The most common flight departure time for this route is 2:00PM, with 64% of daily flights taking off in the afternoon.

The number of flights available between Connecticut 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.