Cheap flights from Simpson Bay to Caribbean Islands from $132

The month of June is, on average, the cheapest month to fly to Caribbean Islands from Simpson Bay, with most prices found around $160. The month of August is another great option to travel to Caribbean Islands, with average flight prices from Simpson Bay averaging around $165.

The cheapest day to depart from Simpson Bay to Caribbean Islands is on a Saturday. Travelers who choose to depart for Caribbean Islands on a Saturday will often find tickets for as low as $203. If your travel schedule is flexible, try to avoid departing on a Monday because tickets tend to average around $357. 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 Simpson Bay to Caribbean Islands in the afternoon for as low as $237. 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 $336. Of course, these prices can vary depending on the time of year and what airport you fly to.

Fly from Simpson Bay Princess Juliana to Santo Domingo Las Americas for the best Simpson Bay Princess Juliana - Caribbean Islands flight prices

You are more likely to see cheaper flights to Caribbean Islands from Simpson Bay when booking weeks ahead of your departure date. In general, you can expect to find flights to Caribbean Islands for around $270 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Caribbean Islands from Simpson Bay for as low as $173 on momondo.

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

FlexFlight, Hahn Air, and Arajet are the most popular carriers operating from Simpson Bay Princess Juliana to Caribbean Islands

Winair, Arajet and Frontier are the top three most popular airlines that fly to Caribbean Islands from Simpson Bay according to our data. Winair is the first choice among our users, with 62% of people opting to fly with this airline when traveling to Caribbean Islands. Keep in mind that there are 6 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 Simpson Bay and Caribbean Islands is 72 per day as of March 2026. The most frequent departure time is 7:00AM, with 73% of daily flights leaving at noon.

The number of flights available between Simpson Bay and Caribbean Islands is 505 per week as of March 2026. The most frequent departure day is Mon, with 15% of weekly flights leaving on this day.