SXM - BOS

$184 Find Cheap Flights from Simpson Bay to Boston

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Simpson Bay to Boston departing on 5/1. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Boston

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Simpson Bay to Boston, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Simpson Bay to Boston, as well as popular online travel agencies
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

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Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Everything you should know

Cheapest round-trip
$276
Typical prices: $335-$381
American Airlines
Wed 5/6Tue 5/12
SXM - BOS • 1 stop
Cheapest non-stop
$361
JetBlue
Sun 3/29Sun 4/5
SXM - BOS • Non-stop
Top airlines
American Airlines
Cheapest • from $276 (round-trip)
American Airlines
Best reviews • 7.1 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Every day
You can fly direct with JetBlue. Average duration is 4h 24m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top layover airports
Washington, D.C. (IAD)
Cheapest • Avg $315 (round-trip)
Washington, D.C. (IAD)
Shortest trip • 8h 09m (one-way)
Insights
Insights
Insights
Insights
When to travel
May
Cheapest • 28% price drop
June
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Boston!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Simpson Bay to Boston (SXM-BOS)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Simpson Bay to Boston that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Simpson Bay to Boston

Wed, May 6 - Tue, May 12
American Airlines Logo
4:35 pm - 12:59 am
SXM
-
BOS
8h 24m
1 stop
American Airlines Logo
6:00 am - 3:22 pm
BOS
-
SXM
9h 22m
2 stops
$276American Airlines
Wed, May 6 - Tue, May 12
Southwest Logo
2:25 pm - 8:05 am
SXM
-
BOS
17h 40m
2 stops
Southwest Logo
4:45 pm - 1:30 pm
BOS
-
SXM
20h 45m
2 stops
$292Southwest
Thu, Mar 26 - Wed, Apr 1
American Airlines Logo
2:21 pm - 10:40 pm
SXM
-
BOS
8h 19m
1 stop
American Airlines Logo
5:00 am - 1:21 pm
BOS
-
SXM
8h 21m
1 stop
$305American Airlines
Wed, Jun 24 - Sun, Jun 28
United Airlines Logo
1:35 pm - 9:39 am
SXM
-
BOS
20h 04m
2 stops
United Airlines Logo
7:19 am - 12:33 pm
BOS
-
SXM
29h 14m
2 stops
$338United Airlines
Wed, Jul 1 - Tue, Jul 14
American Airlines Logo
4:43 pm - 6:50 pm
SXM
-
BOS
26h 07m
2 stops
American Airlines Logo
6:00 am - 3:46 pm
BOS
-
SXM
9h 46m
2 stops
$345American Airlines
Wed, Jun 24 - Mon, Jul 6
United Airlines Logo
1:35 pm - 9:53 pm
SXM
-
BOS
8h 18m
1 stop
United Airlines Logo
8:00 am - 2:43 pm
BOS
-
SXM
6h 43m
1 stop
$346United Airlines
Thu, May 7 - Sat, May 16
American Airlines Logo
2:21 pm - 10:02 am
SXM
-
BOS
19h 41m
1 stop
American Airlines Logo
5:40 pm - 1:21 pm
BOS
-
SXM
19h 41m
1 stop
$347American Airlines
Thu, Apr 2 - Mon, Apr 6
Spirit Airlines Logo
2:35 pm - 11:59 pm
SXM
-
BOS
9h 24m
1 stop
Spirit Airlines Logo
5:45 am - 1:30 pm
BOS
-
SXM
7h 45m
1 stop
$349Spirit Airlines
Thu, Apr 16 - Wed, Apr 22
American Airlines Logo
2:24 pm - 11:07 pm
SXM
-
BOS
8h 43m
1 stop
American Airlines Logo
5:40 pm - 11:37 am
BOS
-
SXM
17h 57m
2 stops
$350American Airlines
Tue, Mar 31 - Mon, Apr 6
American Airlines Logo
4:28 pm - 10:01 am
SXM
-
BOS
17h 33m
1 stop
American Airlines Logo
5:30 pm - 1:21 pm
BOS
-
SXM
19h 51m
1 stop
$352American Airlines
Booking Insights

KAYAK's insights & trends for Simpson Bay to Boston flights

Get data-powered insights and trends into flights from Simpson Bay to Boston to help you find the cheapest flights, the best time to fly and much more.

What’s the cheapest day of the week to fly from Simpson Bay to Boston?

The average price of all round-trip flights from Simpson Bay to Boston clicked on KAYAK for each day over the last 12 months.

If your flying dates are flexible, you should consider flying to Boston on a Tuesday, as we generally find the cheapest rates on that day for this route. On the other hand, Saturday is the most expensive day to fly from Simpson Bay to Boston. For your return ticket, we recommend flying on a Wednesday and avoiding Saturdays for the best deals.

What is the cheapest month to fly from Simpson Bay to Boston?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Simpson Bay to Boston, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Simpson Bay to Boston is May, where tickets cost $335 (return) on average. On the other hand, the most expensive months are November and February, where the average cost of round-trip tickets is $829 and $573 respectively.

Can I save money by flying with a layover from Simpson Bay to Boston?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $315 on average.

Find deals

Good to know

Low seasonAugust
Cheapest flight$184
Best time to beat the crowds with an average 9% drop in price.
Most popular time to fly and prices are also 28% lower on average.
Flight from Simpson Bay to Boston

When to book flights from Simpson Bay to Boston

Are your dates flexible? Find out the best times to travel from Simpson Bay to Boston based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking flights from Simpson Bay to Boston

  • What is the cheapest flight from Simpson Bay to Boston?

    In the last 3 days, the lowest price for a flight from Simpson Bay to Boston was $184 for a one-way ticket and $276 for a round-trip.

  • Do I need a passport to fly between Simpson Bay and Boston?

    Yes, you’ll need a passport to travel to Boston from Simpson Bay.

  • Which airports will I be using when flying from Simpson Bay to Boston?

    When flying out of Simpson Bay you will be using Simpson Bay Princess Juliana. You will be landing at Boston, also known as Boston Logan Intl.

  • Which airlines offer Wi-Fi service onboard planes from Simpson Bay to Boston?

    Only Delta offers inflight Wi-Fi service on the Simpson Bay to Boston flight route.

  • Which aircraft models fly most regularly from Simpson Bay to Boston?

    The Airbus A321-100/200 is the aircraft model that flies most regularly on the Simpson Bay to Boston flight route.

  • Which airline alliances offer flights from Simpson Bay to Boston?

    oneworld is the only airline alliance operating flights between Simpson Bay and Boston.

  • On which days can I fly direct from Simpson Bay to Boston?

    There are nonstop flights from Simpson Bay to Boston on a daily basis.

  • How does KAYAK find such low prices on flights from Simpson Bay to Boston?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Simpson Bay to Boston.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Simpson Bay to Boston?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Boston from Simpson Bay is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Simpson Bay to Boston?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Boston with an airline and back to Simpson Bay with another airline. Booking your flights between Simpson Bay and BOS can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Simpson Bay to Boston?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Boston from Simpson Bay up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Simpson Bay to Boston

  • Looking for a cheap flight? 25% of our users found flights on this route for $259 or less one-way.

Prefer to fly direct from Simpson Bay to Boston?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Simpson Bay Princess Juliana to Boston Logan Intl.
Find which airlines fly direct from Simpson Bay Princess Juliana Airport to Boston Logan Intl Airport, which days they fly and book direct flights.

Direct departures

Simpson Bay Princess Juliana to Boston Logan Intl

Monday

JetBlue

JetBlue

Tuesday

JetBlue

JetBlue

Wednesday

JetBlue

JetBlue

Thursday

JetBlue

JetBlue

Friday

JetBlue

JetBlue

Saturday

JetBlue

JetBlue

Sunday

JetBlue

JetBlue

See more direct flights

Direct returns

Boston Logan Intl to Simpson Bay Princess Juliana

Monday

JetBlue

JetBlue

Tuesday

JetBlue

JetBlue

Wednesday

JetBlue

JetBlue

Thursday

JetBlue

JetBlue

Friday

JetBlue

JetBlue

Saturday

JetBlue

JetBlue

Sunday

JetBlue

JetBlue

See more direct flights

Reviews of the top airline flying from Simpson Bay to Boston

 
See real verified KAYAK customer reviews for airlines flying from Simpson Bay to Boston. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Simpson Bay to Boston? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.1
American AirlinesOverall score based on 11472 reviews
6.9Entertainment
7.5Boarding
6.4Food
7.9Crew
7.2Comfort
Airline reviews

After changing the departure gate 5 times making us mo e from one side of the airport to the other and then back the flight was delayed nearly 2 hours. The male flight attendant had a bad attitude with the guest being condescending, disrespectful with people who were already on edge.

2.0 Mediocresteven, Mar 2026
MIA - CLE
Read more American Airlines reviews

After changing the departure gate 5 times making us mo e from one side of the airport to the other and then back the flight was delayed nearly 2 hours. The male flight attendant had a bad attitude with the guest being condescending, disrespectful with people who were already on edge.

Easy boarding. Rows are smaller but that may be an older and bigger me now :)

It would have been nice if American tried to care.

American Airlines did everything they could with the high Spring Break crowd. I was frustrated to be changed from 1st class to a middle seat at the back of the plane. This has happened before, not sure booking 1st class and paying the extra actually works.

I booked 1st class, my flights were changed and I was sitting in the middle at the back of the plane. A far cry from the 1st class I purchased for my flights. I am grateful I arrived on time.

Movie selections were very limited. Meals were not f So good.

Older airplane with worn out seats. No entertainment system at all. Connecting to Wi-Fi was problematic and hit and miss.

AA is flying sub par aging 787's to Tokyo. I fly other 787's long haul and these are at the bottom. Seats don't work well, tray tables don't work well and were dirty. The flight was great, the plane was not.

There was no beverage service and the only time I saw a crew member walk through the cabin is when we were preparing to land.

Our flight was delayed 3 times and this is why I am giving such low reviews. Everything else was okay but being in the airport at 4:30pm for my initial flight at 7pm to not leave until after 9:30pm is insane,

Everything you need to know for your flight from Simpson Bay to Boston

Information on your arrival and departure airports

Simpson Bay (SXM)
Boston (BOS)