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Simpson Bay

$322+ 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 9/22. Fares are subject to change and may not be available on all flights or dates of travel.
RSW — SXM
Oct 16 — Oct 231
Thu 10/16
Thu 10/23
1 adult, Economy
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Cheap 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 September 16, 2025.

Round-trip from

$463
(Expedia)

One-way from

$322
(Kiwi.com)

Popular in

August

Cheapest in

November

Average price

$601
From Fort Myers SW Florida Intl to Simpson Bay Princess Juliana
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One-way flight from Fort Myers SW Florida Intl to Simpson Bay Princess Juliana
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Highest demand for flights based on searches. 10% potential increase in price ($74 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($18 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find 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 September 16, 2025.

This Expedia deal was found by Cheapflights users on 9/14. 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 11/106:13 amRSW - SXM
1 stop9h 25mJetBlue
Thu 11/135:44 pmSXM - RSW
1 stop28h 00mJetBlue
Deal found 9/14$463
This Expedia deal was found by Cheapflights users on 9/16. 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.
Sat 11/156:13 amRSW - SXM
1 stop9h 25mJetBlue
Thu 11/204:15 pmSXM - RSW
1 stop18h 58mJetBlue
Deal found 9/16$485
This Expedia deal was found by Cheapflights users on 9/16. 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 12/86:00 amRSW - SXM
1 stop9h 38mJetBlue
Mon 12/154:10 pmSXM - RSW
2 stops29h 35mJetBlue
Deal found 9/16$517
This American Airlines deal was found by Cheapflights users on 9/14. 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 11/97:21 pmRSW - SXM
1 stop17h 29mAmerican Airlines
Wed 11/122:51 pmSXM - RSW
1 stop9h 38mAmerican Airlines
Deal found 9/14$539
This American Airlines deal was found by Cheapflights users on 9/14. 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 11/106:33 pmRSW - SXM
2 stops20h 49mAmerican Airlines
Thu 11/132:51 pmSXM - RSW
1 stop10h 36mAmerican Airlines
Deal found 9/14$544
This American Airlines deal was found by Cheapflights users on 9/15. 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.
Tue 11/188:40 amRSW - SXM
1 stop28h 10mAmerican Airlines
Wed 11/262:51 pmSXM - RSW
1 stop10h 57mAmerican Airlines
Deal found 9/15$548
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 12/811:45 amRSW - SXM
1 stop26h 36mWestJet
Mon 12/154:20 pmSXM - RSW
1 stop19h 40mWestJet
Deal found 9/16$561
This American Airlines deal was found by Cheapflights users on 9/16. 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 12/86:25 pmRSW - SXM
2 stops18h 55mAmerican Airlines
Mon 12/155:25 pmSXM - RSW
2 stops20h 07mAmerican Airlines
Deal found 9/16$569
This Mytrip deal was found by Cheapflights users on 9/14. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/97:11 pmRSW - SXM
2 stops18h 59mSpirit Airlines
Wed 11/124:28 pmSXM - RSW
3 stops26h 38mSpirit Airlines
Deal found 9/14$593
This Mytrip deal was found by Cheapflights users on 9/15. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/107:11 pmRSW - SXM
3 stops42h 59mMultiple Airlines
Thu 11/131:05 pmSXM - RSW
2 stops22h 55mMultiple Airlines
Deal found 9/15$651
This WestJet deal was found by Cheapflights users on 9/15. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/3011:45 amRSW - SXM
1 stop26h 36mWestJet
Thu 11/64:20 pmSXM - RSW
1 stop19h 40mWestJet
Deal found 9/15$760

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 September 16, 2025.
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

Sat 11/15

6:13 am-4:38 pm

1 stop9h 25m

Simpson Bay Princess Juliana

Thu 11/20

4:15 pm-10:13 am

1 stop18h 58m

$485

Fort MyersSimpson Bay

RSW - SXM

RSWSXM

Fort Myers SW Florida Intl

Sun 3/8

7:30 pm-11:15 am

1 stop15h 45m

Simpson Bay Princess Juliana

Wed 3/11

3:45 pm-10:54 am

1 stop19h 09m

$515

Fort MyersSimpson Bay

RSW - SXM

RSWSXM

Fort Myers SW Florida Intl

Mon 12/8

6:00 am-4:38 pm

1 stop9h 38m

Simpson Bay Princess Juliana

Mon 12/15

4:10 pm-8:45 pm

2 stops29h 35m

$517

Fort MyersSimpson Bay

RSW - SXM

RSWSXM

Fort Myers SW Florida Intl

Sun 1/18

5:35 am-2:56 pm

1 stop8h 21m

Simpson Bay Princess Juliana

Sat 1/24

5:16 pm-12:37 am

1 stop8h 21m

$540

Fort MyersSimpson Bay

RSW - SXM

RSWSXM

Fort Myers SW Florida Intl

Mon 11/10

6:33 pm-2:19 pm

2 stops18h 46m

Simpson Bay Princess Juliana

Thu 11/13

5:24 pm-12:21 pm

2 stops19h 57m

$544

Fort MyersSimpson Bay

RSW - SXM

RSWSXM

Fort Myers SW Florida Intl

Sat 11/15

5:34 pm-2:00 pm

2 stops19h 26m

Simpson Bay Princess Juliana

Thu 11/20

2:51 pm-12:48 am

1 stop10h 57m

$544

Fort MyersSimpson Bay

RSW - SXM

RSWSXM

Fort Myers SW Florida Intl

Sun 2/22

7:51 pm-3:10 pm

2 stops18h 19m

Simpson Bay Princess Juliana

Thu 2/26

4:15 pm-10:46 am

2 stops19h 31m

$544

Fort MyersSimpson Bay

RSW - SXM

RSWSXM

Fort Myers SW Florida Intl

Mon 9/22

7:00 am-8:12 am

3 stops49h 12m

$322

Fort MyersSimpson Bay

RSW - SXM

RSWSXM

Fort Myers SW Florida Intl

Mon 9/22

4:35 pm-1:19 pm

2 stops20h 44m

$389

Fort MyersSimpson Bay

RSW - SXM

RSWSXM

Fort Myers SW Florida Intl

Mon 9/22

7:00 am-1:50 pm

1 stop6h 50m

$399

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

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.

Cheapflights Insights

Everything you need to know about your flight from Fort Myers to Simpson Bay

How much does it cost to fly round-trip from Fort Myers 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 September 16, 2025.
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
8.0
Very good
7,957 reviews

Boarding

8.2

Crew

8.5

Food

7.3

Comfort

7.9

Entertainment

7.9

Overall

8.0

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
8.0
Very good
7,957 reviews
Delta
8.0
Very good
7,957 reviews

Boarding

8.2

Crew

8.5

Food

7.3

Comfort

7.9

Entertainment

7.9

Overall

8.0

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
10,000 reviews
Delta
8.0
Very good
7,957 reviews

Boarding

8.2

Crew

8.5

Food

7.3

Comfort

7.9

Entertainment

7.9

Overall

8.0

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 9h 25m. Fly via JetBlue or Delta 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.

  • What is the cheapest month to book a flight from Fort Myers to Simpson Bay?

    Currently, September is the cheapest month in which you can book a flight from Fort Myers to Simpson Bay (average of $459). Flying from Fort Myers to Simpson Bay in March is currently the most expensive (average of $652). 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

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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 September 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$494Average$595FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$514Average$700FlexibilityNo cancel feeOn-time71%

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