Cheap flights from Boston to Simpson Bay from $94

In general, September is the cheapest month to fly from Boston to Simpson Bay. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $419. If you aren’t able to travel to Simpson Bay during the month of September, then flying in March is also cheap. Prices for this month can be found on momondo for an average of $451.

Our data shows that Monday is the least expensive day to fly to Simpson Bay. Tickets to fly out on this day can be as low as $440. Flights from Boston to Simpson Bay on a Saturday will generally be more expensive and average around $704. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

Fly from Boston Logan Intl to Simpson Bay Princess Juliana for the best Boston Logan Intl - Simpson Bay Princess Juliana flight prices

You are more likely to see cheaper flights to Simpson Bay from Boston when booking weeks ahead of your departure date. In general, you can expect to find flights to Simpson Bay for around $533 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Simpson Bay from Boston for as low as $435 on momondo.

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

As of October 2026, prices for Boston to Simpson Bay flights are approximately 116% more expensive when compared to flights at the same time last year.

United Airlines and JetBlue are the most popular carriers operating from Boston Logan Intl to Simpson Bay Princess Juliana

JetBlue, American Airlines and United Airlines are the top three most popular airlines that fly to Simpson Bay from Boston according to our data. JetBlue is the first choice among our users, with 64% of people opting to fly with this airline when traveling to Simpson Bay. Keep in mind that there are 5 different airlines that fly to Simpson Bay on a routine basis, so you have a few additional options to choose from.

Miami (MIA) was the most common stop: 50% of momondo users choosing 1-stop flights on this route connected there.

Flights via Newark (EWR) offer the lowest average round-trip price of $285.

Flights connecting via Newark (EWR) have the shortest average one-way travel time: 6h 50m.

Miami (MIA) has the shortest average layover time for this route: 1h 25m.