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Simpson Bay

$157+ Cheap flights from Fort Myers (RSW) 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 2/8. Fares are subject to change and may not be available on all flights or dates of travel.
RSW — SXM
Feb 20 — Feb 271
Fri 2/20
Fri 2/27
1 adult, Economy
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Cheap flight deals from Fort Myers to Simpson Bay

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

This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/297:36 pm
RSW
-
SXM
2 stops41h 34m
Multiple Airlines
Fri 2/64:20 pm
SXM
-
RSW
1 stop19h 07m
Multiple Airlines
Deal found 1/20$542
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/22:25 pm
RSW
-
SXM
1 stop23h 52m
Multiple Airlines
Sat 2/73:20 pm
SXM
-
RSW
2 stops28h 21m
Multiple Airlines
Deal found 1/20$550
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/111:25 am
RSW
-
SXM
1 stop23h 30m
Multiple Airlines
Sat 2/73:20 pm
SXM
-
RSW
2 stops28h 21m
Multiple Airlines
Deal found 1/20$553
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/167:09 pm
RSW
-
SXM
1 stop18h 35m
JetBlue
Fri 3/204:50 pm
SXM
-
RSW
1 stop25h 56m
JetBlue
Deal found 1/20$555
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/227:20 am
RSW
-
SXM
1 stop6h 20m
Southwest
Thu 4/302:35 pm
SXM
-
RSW
1 stop7h 10m
Southwest
Deal found 1/20$565
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/17:36 pm
RSW
-
SXM
2 stops17h 39m
Multiple Airlines
Fri 2/64:20 pm
SXM
-
RSW
1 stop19h 07m
Multiple Airlines
Deal found 1/20$570
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.
Wed 4/226:00 am
RSW
-
SXM
2 stops9h 20m
American Airlines
Thu 4/304:35 pm
SXM
-
RSW
2 stops20h 25m
American Airlines
Deal found 1/20$572
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.
Mon 3/164:19 pm
RSW
-
SXM
2 stops21h 02m
American Airlines
Fri 3/204:01 pm
SXM
-
RSW
1 stop29h 54m
American Airlines
Deal found 1/20$582
This Southwest deal was found by Cheapflights users on 1/18. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/196:40 am
RSW
-
SXM
1 stop7h 45m
Southwest
Sat 4/251:20 pm
SXM
-
RSW
2 stops19h 40m
Southwest
Deal found 1/18$590
This American Airlines deal was found by Cheapflights users on 1/18. 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 4/197:41 pm
RSW
-
SXM
1 stop17h 40m
American Airlines
Sat 4/253:32 pm
SXM
-
RSW
1 stop18h 04m
American Airlines
Deal found 1/18$592
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/309:11 pm
RSW
-
SXM
2 stops15h 59m
Multiple Airlines
Fri 2/64:20 pm
SXM
-
RSW
1 stop19h 07m
Multiple Airlines
Deal found 1/20$593

Find flight deals from Fort Myers to Simpson Bay

Discover tips and strategies to find the most affordable flight options for your journey from Fort Myers (RSW) 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

$550
(Kiwi.com)

One-way from

$157
(Kiwi.com)

Popular in

August

Cheapest in

November

Average price

$720
Provider with most accurate pricing for Fort Myers SW Florida Intl-Simpson Bay Princess Juliana flight deals.
Search Deals
Provider most trusted by Cheapflights users for Fort Myers SW Florida Intl-Simpson Bay Princess Juliana flights.
Search Deals
From Fort Myers SW Florida Intl to Simpson Bay Princess Juliana
Search Deals
One-way flight from Fort Myers SW Florida Intl to Simpson Bay Princess Juliana
Search Deals
Highest demand for flights based on searches. 9% potential increase in price ($69 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($17 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 Fort Myers 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 Fort Myers to Simpson Bay that are best for you.

Fly from

Fort Myers

Fly to

Simpson Bay

Route

Depart

Return

Price

Fort MyersSimpson Bay

RSW - SXM

RSWSXM

Fort Myers SW Florida Intl

Mon 2/2

2:25 pm-3:17 pm

1 stop23h 52m

Simpson Bay Princess Juliana

Sat 2/7

3:20 pm-6:41 pm

2 stops28h 21m

$550

Fort MyersSimpson Bay

RSW - SXM

RSWSXM

Fort Myers SW Florida Intl

Sun 2/1

11:25 am-11:55 am

1 stop23h 30m

Simpson Bay Princess Juliana

Sat 2/7

3:20 pm-6:41 pm

2 stops28h 21m

$553

Fort MyersSimpson Bay

RSW - SXM

RSWSXM

Fort Myers SW Florida Intl

Wed 4/22

7:20 am-1:40 pm

1 stop6h 20m

Simpson Bay Princess Juliana

Thu 4/30

2:35 pm-9:45 pm

1 stop7h 10m

$565

Fort MyersSimpson Bay

RSW - SXM

RSWSXM

Fort Myers SW Florida Intl

Mon 3/16

4:19 pm-1:21 pm

2 stops21h 02m

Simpson Bay Princess Juliana

Fri 3/20

4:01 pm-9:55 pm

1 stop29h 54m

$582

Fort MyersSimpson Bay

RSW - SXM

RSWSXM

Fort Myers SW Florida Intl

Sun 4/19

6:40 am-2:25 pm

1 stop7h 45m

Simpson Bay Princess Juliana

Sat 4/25

1:20 pm-9:00 am

2 stops19h 40m

$590

Fort MyersSimpson Bay

RSW - SXM

RSWSXM

Fort Myers SW Florida Intl

Sun 4/19

7:41 pm-1:21 pm

1 stop17h 40m

Simpson Bay Princess Juliana

Sat 4/25

3:32 pm-9:36 am

1 stop18h 04m

$592

Fort MyersSimpson Bay

RSW - SXM

RSWSXM

Fort Myers SW Florida Intl

Wed 2/4

5:23 pm-2:15 pm

2 stops19h 52m

Simpson Bay Princess Juliana

Mon 2/9

4:20 pm-10:55 am

1 stop19h 35m

$597

Fort MyersSimpson Bay

RSW - SXM

RSWSXM

Fort Myers SW Florida Intl

Sat 2/28

6:26 pm-2:19 pm

2 stops18h 53m

Simpson Bay Princess Juliana

Sat 3/14

4:28 pm-11:26 am

2 stops18h 58m

$615

Fort MyersSimpson Bay

RSW - SXM

RSWSXM

Fort Myers SW Florida Intl

Sun 2/8

7:36 pm-2:15 pm

2 stops17h 39m

$157

Fort MyersSimpson Bay

RSW - SXM

RSWSXM

Fort Myers SW Florida Intl

Fri 2/6

7:31 am-2:15 pm

2 stops29h 44m

$203

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/19

Showing 1-10 of 19 results
1
2

Compare providers for flights from Fort Myers 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 Fort Myers to Simpson Bay in January.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*1 star
ExpediaPrice Accuracy2 starsTrust Score*3 stars
AranGrantPrice Accuracy2 starsTrust Score*3 stars

*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 Fort Myers-Simpson Bay flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Fort Myers-Simpson Bay flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Fort Myers-Simpson Bay flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Fort Myers-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 Fort Myers-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 Fort Myers to Simpson Bay

Have a flexible travel schedule? Discover the best time to fly to Simpson Bay from Fort Myers 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.

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 Fort Myers 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

Entertainment

7.8

Comfort

7.9

Crew

8.5

Food

7.2

Reviews

1 / 20
6.0
Good

pilar,May 2025

RSW - ATL

The stewardess was not very nice because I requested two glasses of water. She didn’t even offer the snacks to me. She seemed angry and I felt very bad about her reaction. Also, the flight was full and you could not move. The airline should provide seats for obese people in consideration to the rest pf the passengers.
Delta
7.9
Good
8,088 reviews
Delta
7.9
Good
8,088 reviews

Boarding

8.1

Overall

7.9

Entertainment

7.8

Comfort

7.9

Crew

8.5

Food

7.2

Reviews

1 / 20
6.0
Good

pilar,May 2025

RSW - ATL

The stewardess was not very nice because I requested two glasses of water. She didn’t even offer the snacks to me. She seemed angry and I felt very bad about her reaction. Also, the flight was full and you could not move. The airline should provide seats for obese people in consideration to the rest pf the passengers.
American Airlines
7.2
Good
11,174 reviews
Delta
7.9
Good
8,088 reviews

Boarding

8.1

Overall

7.9

Entertainment

7.8

Comfort

7.9

Crew

8.5

Food

7.2

Reviews

1 / 20
6.0
Good

pilar,May 2025

RSW - ATL

The stewardess was not very nice because I requested two glasses of water. She didn’t even offer the snacks to me. She seemed angry and I felt very bad about her reaction. Also, the flight was full and you could not move. The airline should provide seats for obese people in consideration to the rest pf the passengers.

Related info for your journey

Find useful and relevant information for your journey from Fort Myers 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 Fort Myers to Simpson Bay?

    There are many flights that can get you from Fort Myers to Simpson Bay in 6h 20m. Fly via Southwest or American Airlines to get the fastest option. Airlines will cover a distance of 1326 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines flying from Fort Myers to Simpson Bay round-trip?

    According to our current data, Delta ($494), and American Airlines ($514) offers the cheapest pricing from Fort Myers to Simpson Bay. Delta is priced at 25% lower than the current average price of a flight leaving 3 months from now.

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

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

  • How can I find direct flights from Fort Myers to Simpson Bay?

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

  • Can I find deals for business class flights from Fort Myers to Simpson Bay?

    Yes. Cheapflights offers flight deals from Fort Myers 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.

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

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Top 2 airlines flying from Fort Myers to Simpson Bay

Discover the top 2 airlines that operate flights from Fort Myers 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$494Average$662FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$514Average$610FlexibilityNo cancel feeOn-time71%

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