Cheap flights from Hartford to Caribbean Islands from $111

The month of October is, on average, the cheapest month to fly to Caribbean Islands from Hartford, with most prices found around $120. The month of September is another great option to travel to Caribbean Islands, with average flight prices from Hartford averaging around $127.

The cheapest day to depart from Hartford to Caribbean Islands is on a Tuesday. Travelers who choose to depart for Caribbean Islands on a Tuesday will often find tickets for as low as $355. If your travel schedule is flexible, try to avoid departing on a Friday because tickets tend to average around $406. 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 at noon. momondo users have found flights departing from Hartford to Caribbean Islands at noon for as low as $346. 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 in the morning because they tend to be around $392. 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 Hartford Bradley Intl - Caribbean Islands flight prices

You are more likely to see cheaper flights to Caribbean Islands from Hartford when booking weeks ahead of your departure date. In general, you can expect to find flights to Caribbean Islands for around $364 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Caribbean Islands from Hartford for as low as $345 on momondo.

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

United Airlines, Southwest, and American Airlines are the most popular carriers operating from Hartford Bradley Intl to Caribbean Islands

JetBlue, American Airlines and Avelo Airlines are the top three most popular airlines that fly to Caribbean Islands from Hartford according to our data. JetBlue is the first choice among our users, with 73% of people opting to fly with this airline when traveling to Caribbean Islands. Keep in mind that there are 7 different airlines that fly to Caribbean Islands on a routine basis, so you have a few additional options to choose from.

The number of flights available between Hartford and Caribbean Islands is 3 per day as of June 2026. The most frequent departure time is 11:00AM, with 37% of daily flights leaving at noon.

As of June 2026, 21 flights take off from Hartford and land in Caribbean Islands each week. The most common flight departure day for this route is Mon, with 14% of weekly flights taking off on this day.