Cheap flights from Simpson Bay to Caribbean Islands from $134

The month of July is, on average, the cheapest month to fly to Caribbean Islands from Simpson Bay, with most prices found around $76. The month of January is another great option to travel to Caribbean Islands, with average flight prices from Simpson Bay averaging around $80.

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 $383. 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 $234. 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 $352. 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 $301 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 $181 on momondo.

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

Arajet, Winair and Caribbean Airlines are the top three most popular airlines that fly to Caribbean Islands from Simpson Bay according to our data. Arajet is the first choice among our users, with 51% 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 Simpson Bay and Caribbean Islands is 53 per day as of May 2026. The most frequent departure time is 1:00PM, with 75% of daily flights leaving in the afternoon.

The number of flights available between Simpson Bay and Caribbean Islands is 373 per week as of May 2026. The most frequent departure day is Fri, with 16% of weekly flights leaving on this day.