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Simpson Bay

$163+ Cheap flights from San Diego (SAN) to Simpson Bay (SXM)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 3/11. Fares are subject to change and may not be available on all flights or dates of travel.
SAN — SXM
Feb 20 — Feb 271
Fri 2/20
Fri 2/27
1 adult, Economy
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Cheap flight deals from San Diego to Simpson Bay

Cheapest flights from San Diego to Simpson Bay
Explore the most affordable flight options available from San Diego to Simpson Bay. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 21, 2026.

This American Airlines deal was found by Cheapflights users on 1/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/279:57 pm
SAN
-
SXM
1 stop14h 02m
American Airlines
Thu 3/53:17 pm
SXM
-
SAN
1 stop11h 23m
American Airlines
Deal found 1/21$415
This United Airlines deal was found by Cheapflights users on 1/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/118:50 pm
SAN
-
SXM
2 stops13h 00m
United Airlines
Mon 3/163:55 pm
SXM
-
SAN
2 stops20h 52m
United Airlines
Deal found 1/19$420
This United Airlines deal was found by Cheapflights users on 1/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/910:30 pm
SAN
-
SXM
1 stop13h 21m
United Airlines
Sun 3/151:20 pm
SXM
-
SAN
1 stop23h 27m
United Airlines
Deal found 1/20$424
This American Airlines deal was found by Cheapflights users on 1/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/810:25 pm
SAN
-
SXM
1 stop14h 03m
American Airlines
Mon 2/165:01 pm
SXM
-
SAN
1 stop22h 44m
American Airlines
Deal found 1/20$473
This United Airlines deal was found by Cheapflights users on 1/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/810:40 pm
SAN
-
SXM
1 stop11h 10m
United Airlines
Sun 2/154:55 pm
SXM
-
SAN
2 stops22h 43m
United Airlines
Deal found 1/20$478
This American Airlines deal was found by Cheapflights users on 1/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/84:00 pm
SAN
-
SXM
2 stops16h 58m
American Airlines
Sun 2/153:17 pm
SXM
-
SAN
2 stops21h 36m
American Airlines
Deal found 1/20$483
This American Airlines deal was found by Cheapflights users on 1/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/1310:41 pm
SAN
-
SXM
1 stop10h 44m
American Airlines
Mon 11/165:24 pm
SXM
-
SAN
2 stops20h 33m
American Airlines
Deal found 1/20$509
This American Airlines deal was found by Cheapflights users on 1/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/57:30 pm
SAN
-
SXM
2 stops14h 30m
American Airlines
Sun 11/152:51 pm
SXM
-
SAN
2 stops21h 43m
American Airlines
Deal found 1/20$549

Find flight deals from San Diego to Simpson Bay

Discover tips and strategies to find the most affordable flight options for your journey from San Diego (SAN) to Simpson Bay (SXM). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated January 21, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$415
(American Airlines)

One-way from

$144
(Expedia)

Popular in

November

Cheapest in

October

Average price

$746
Provider with most accurate pricing for San Diego-Simpson Bay Princess Juliana flight deals.
Search Deals
Provider most trusted by Cheapflights users for San Diego-Simpson Bay Princess Juliana flights.
Search Deals
From San Diego to Simpson Bay Princess Juliana
Search Deals
One-way flight from San Diego to Simpson Bay Princess Juliana
Search Deals
Highest demand for flights based on searches. 13% potential increase in price ($126 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease ($50 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from San Diego to Simpson Bay that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated January 21, 2026.
Use the filters below to find and compare flights from San Diego to Simpson Bay that are best for you.

Fly from

San Diego

Fly to

Simpson Bay

Route

Depart

Return

Price

San DiegoSimpson Bay

SAN - SXM

SANSXM

San Diego

Fri 2/27

9:57 pm-3:59 pm

1 stop14h 02m

Simpson Bay Princess Juliana

Thu 3/5

3:17 pm-10:40 pm

1 stop11h 23m

$415

San DiegoSimpson Bay

SAN - SXM

SANSXM

San Diego

Wed 3/11

1:37 pm-1:16 pm

1 stop20h 39m

Simpson Bay Princess Juliana

Mon 3/16

4:01 pm-11:44 am

1 stop22h 43m

$415

San DiegoSimpson Bay

SAN - SXM

SANSXM

San Diego

Wed 3/11

8:50 pm-12:50 pm

2 stops13h 00m

Simpson Bay Princess Juliana

Mon 3/16

3:55 pm-9:47 am

2 stops20h 52m

$420

San DiegoSimpson Bay

SAN - SXM

SANSXM

San Diego

Sat 2/28

4:10 pm-1:50 pm

2 stops17h 40m

Simpson Bay Princess Juliana

Thu 3/5

4:55 pm-8:40 am

2 stops19h 45m

$420

San DiegoSimpson Bay

SAN - SXM

SANSXM

San Diego

Sat 2/28

9:57 pm-2:16 pm

1 stop12h 19m

Simpson Bay Princess Juliana

Thu 3/5

5:28 pm-8:44 am

2 stops19h 16m

$420

San DiegoSimpson Bay

SAN - SXM

SANSXM

San Diego

Mon 3/9

10:30 pm-2:51 pm

1 stop13h 21m

Simpson Bay Princess Juliana

Sun 3/15

1:20 pm-9:47 am

1 stop23h 27m

$424

San DiegoSimpson Bay

SAN - SXM

SANSXM

San Diego

Sun 2/8

10:25 pm-4:28 pm

1 stop14h 03m

Simpson Bay Princess Juliana

Mon 2/16

5:01 pm-11:45 am

1 stop22h 44m

$473

San DiegoSimpson Bay

SAN - SXM

SANSXM

San Diego

Wed 3/11

9:41 pm-3:00 pm

1 stop14h 19m

$163

San DiegoSimpson Bay

SAN - SXM

SANSXM

San Diego

Wed 3/11

5:55 pm-2:51 pm

2 stops17h 56m

$163

San DiegoSimpson Bay

SAN - SXM

SANSXM

San Diego

Sat 2/7

9:00 pm-2:23 pm

1 stop13h 23m

$205

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/21

Showing 1-10 of 13 results
1
2

Compare providers for flights from San Diego to Simpson Bay

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from San Diego to Simpson Bay in January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on San Diego-Simpson Bay flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on San Diego-Simpson Bay flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from San Diego-Simpson Bay flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on San Diego-Simpson Bay flights, Cheapflights users trust Expedia the most. Expedia has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for San Diego-Simpson Bay flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from San Diego to Simpson Bay

Have a flexible travel schedule? Discover the best time to fly to Simpson Bay from San Diego with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from San Diego to Simpson Bay

What is the cheapest month to book a flight from San Diego to Simpson Bay?

Currently, October is the cheapest month in which you can book a flight from San Diego to Simpson Bay (average of $266). Flying from San Diego to Simpson Bay in November is currently the most expensive (average of $832). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

How much does it cost to fly round-trip from San Diego to Simpson Bay?

Reviews of airlines servicing Simpson Bay

Get insights into the airlines that provide service to Simpson Bay. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Simpson Bay. Reviews last updated January 21, 2026.
Peruse reviews from past customers who have flown with Delta and American Airlines from San Diego to Simpson Bay to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
8,088 reviews

Boarding

8.1

Overall

7.9

Crew

8.5

Entertainment

7.8

Food

7.2

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Delta
7.9
Good
8,088 reviews
Delta
7.9
Good
8,088 reviews

Boarding

8.1

Overall

7.9

Crew

8.5

Entertainment

7.8

Food

7.2

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
American Airlines
7.2
Good
11,174 reviews
Delta
7.9
Good
8,088 reviews

Boarding

8.1

Overall

7.9

Crew

8.5

Entertainment

7.8

Food

7.2

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

Related info for your journey

Find useful and relevant information for your journey from San Diego to Simpson Bay. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from San Diego to Simpson Bay?

    Airlines like American Airlines and United Airlines fly from San Diego to Simpson Bay in about 13h. The time it takes to get you to your destination can typically vary by up to 1h 02m. The distance between San Diego and Simpson Bay is about 3484 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines flying from San Diego to Simpson Bay round-trip?

    Cheapflights users have booked flights from San Diego to Simpson Bay round-trip from $266. Another airline that can offer you cheap pricing is American Airlines. Users have found that Delta is 66% cheaper than the other options available to this destination.

  • Can I find deals for flights from San Diego to Simpson Bay that include hotel bookings?

    Yes. In addition to deals on San Diego to Simpson Bay flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from San Diego to Simpson Bay?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from San Diego to Simpson Bay.

  • Can I find deals for business class flights from San Diego to Simpson Bay?

    Yes. Cheapflights offers flight deals from San Diego to Simpson Bay by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from San Diego to Simpson Bay?

    Currently, October is the cheapest month in which you can book a flight from San Diego to Simpson Bay (average of $266). Flying from San Diego to Simpson Bay in November is currently the most expensive (average of $832). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Simpson Bay?

Book flights to Simpson Bay if you plan to visit one of these locations
Philipsburg

Browse thousands of different options on Cheapflights for your next trip

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Top 2 airlines flying from San Diego to Simpson Bay

Discover the top 2 airlines that operate flights from San Diego to Simpson Bay. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated January 21, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$266Average$769FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$453Average$835FlexibilityNo cancel feeOn-time71%

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