RSW - SXM

$585 Find Cheap Flights from Fort Myers to Simpson Bay

This is the cheapest round-trip flight price found by a KAYAK user in the last 72 hours by searching for a flight from Fort Myers to Simpson Bay departing on 6/10. 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 Simpson Bay

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Fort Myers to Simpson Bay, 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 Fort Myers to Simpson Bay, as well as popular online travel agencies
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Everything you should know

Cheapest round-trip
$585
Southwest
mer. 6/10mer. 6/17
RSW - SXM • 1 stop
Top airlines
Cheapest • from $585 (round-trip)
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Not available
There are currently no direct flights between Fort Myers and Simpson Bay. You'll need at least 1 connection.
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $680 (round-trip)
Shortest trip • 6h 29m (one-way)
Insights
Insights
Insights
Insights
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We hope you love your trip to Simpson Bay!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Fort Myers to Simpson Bay (RSW-SXM)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Fort Myers to Simpson Bay 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 Fort Myers to Simpson Bay

mer., juin 10 - mer., juin 17
Southwest Logo
6:10 am - 2:00 pm
RSW
-
SXM
7h 50m
1 stop
Southwest Logo
3:00 pm - 10:00 pm
SXM
-
RSW
7h 00m
1 stop
$585Southwest
sam., juil. 11 - ven., juil. 17
Southwest Logo
6:20 am - 3:05 pm
RSW
-
SXM
8h 45m
1 stop
Southwest Logo
2:25 pm - 9:55 pm
SXM
-
RSW
7h 30m
1 stop
$620Southwest
sam., juil. 11 - ven., juil. 17
Southwest Logo
6:20 am - 3:05 pm
RSW
-
SXM
8h 45m
1 stop
Southwest Logo
2:25 pm - 9:35 am
SXM
-
RSW
19h 10m
2 stops
$625Southwest
sam., juil. 11 - ven., juil. 17
American Airlines Logo
3:59 pm - 1:19 pm
RSW
-
SXM
21h 20m
2 stops
American Airlines Logo
4:45 pm - 3:09 pm
SXM
-
RSW
22h 24m
2 stops
$642American Airlines
mer., juil. 1 - mar., juil. 7
American Airlines Logo
6:16 am - 1:50 pm
RSW
-
SXM
7h 34m
1 stop
American Airlines Logo
4:45 pm - 1:56 pm
SXM
-
RSW
21h 11m
2 stops
$647American Airlines
sam., oct. 24 - sam., oct. 31
Southwest Logo
7:10 am - 1:45 pm
RSW
-
SXM
6h 35m
1 stop
Southwest Logo
2:45 pm - 9:55 pm
SXM
-
RSW
7h 10m
1 stop
$655Southwest
mer., juil. 1 - mar., juil. 7
American Airlines Logo
6:16 am - 1:50 pm
RSW
-
SXM
7h 34m
1 stop
American Airlines Logo
2:51 pm - 9:08 am
SXM
-
RSW
18h 17m
1 stop
$672American Airlines
sam., oct. 24 - sam., oct. 31
American Airlines Logo
7:54 pm - 3:05 pm
RSW
-
SXM
19h 11m
2 stops
American Airlines Logo
2:35 pm - 10:05 pm
SXM
-
RSW
7h 30m
1 stop
$677American Airlines
jeu., juin 11 - jeu., juin 18
United Airlines Logo
6:02 am - 2:43 pm
RSW
-
SXM
8h 41m
1 stop
United Airlines Logo
3:50 pm - 10:53 am
SXM
-
RSW
19h 03m
1 stop
$682United Airlines
lun., juin 29 - sam., juil. 4
American Airlines Logo
6:16 am - 1:50 pm
RSW
-
SXM
7h 34m
1 stop
American Airlines Logo
2:46 pm - 11:26 am
SXM
-
RSW
20h 40m
1 stop
$685American Airlines
Booking Insights

KAYAK's insights & trends for Fort Myers to Simpson Bay flights

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

Which airlines provide the cheapest flights from Fort Myers to Simpson Bay?

The cheapest round-trip price for the route for each airline clicked by KAYAK users in the last 72 hours.

In the past 3 days, the cheapest round-trip tickets from Fort Myers to Simpson Bay were found on Southwest ($585) and American Airlines ($642).

Good to know

Cheapest flight$585
Flight from Fort Myers to Simpson Bay

When to book flights from Fort Myers to Simpson Bay

Are your dates flexible? Find out the best times to travel from Fort Myers to Simpson Bay 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 Fort Myers to Simpson Bay

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

    In the last 3 days, the lowest price for a flight from Fort Myers to Simpson Bay was $585 for a round-trip ticket.

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

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

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

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Fort Myers to Simpson Bay?

    oneworld, and SkyTeam are the airline alliances operating flights between Fort Myers and Simpson Bay, with oneworld being the most commonly used for this route.

  • Which is the best airline for flights from Fort Myers to Simpson Bay, Delta or American Airlines?

    The two airlines most popular with KAYAK users for flights from Fort Myers to Simpson Bay are Delta and American Airlines. With an average price for the route of $717 and an overall rating of 7.9, Delta is the most popular choice. American Airlines is also a great choice for the route, with an average price of $608 and an overall rating of 7.1.

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

    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 Fort Myers to Simpson Bay.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Simpson Bay from Fort Myers 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 Fort Myers to Simpson Bay?

    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 Simpson Bay with an airline and back to Fort Myers with another airline. Booking your flights between Fort Myers and SXM 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 Fort Myers to Simpson Bay?

    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 Simpson Bay from Fort Myers up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airlines flying from Fort Myers to Simpson Bay

 
See real verified KAYAK customer reviews for airlines flying from Fort Myers to Simpson Bay. 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 Fort Myers to Simpson Bay? 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.
7.9
DeltaOverall score based on 8464 reviews
7.8Entertainment
7.9Comfort
7.2Food
8.1Boarding
8.5Crew
Airline reviews

The flight was operated by Latam. The aircraft had a technical issue and the flight was delayed for the next day. They grounded other passengers to get their airplane assigned to my flight. Most of he ground staff don't speak English (Orlando Airport), but were very polite.The crew on the other hand could speak English and Portuguese. On board service was good.

6.0 GoodSilvestre, Apr 2026
MCO - GRU
Read more Delta reviews

The flight was operated by Latam. The aircraft had a technical issue and the flight was delayed for the next day. They grounded other passengers to get their airplane assigned to my flight. Most of he ground staff don't speak English (Orlando Airport), but were very polite.The crew on the other hand could speak English and Portuguese. On board service was good.

Flight was delayed it was hot while sitting on the plane, one engine was working on the plane until they had to do some jimmy rigging down the runway in order for the other engine to charge up. It was ridiculous

The flight was very good and the staff was very friendly and helpful!

Landed without a gate ready. Plane is extremely old and dirty.

All the amenities was wonderful, if they could keep their prices that low. I'd fly with them all the time.

The WiFi was horrific. I fly delta often and love their (usually reliable and free) WiFi. On this flight it was intermittent and when it did connect was extremely slow. I couldn’t get any work done while I was on the flight which was extremely frustrating. I was also in the exit row seat where there is now immediate seat in front of you, so while the leg room was nice, I couldn’t even watch the TV when the internet wasn’t working. Finally, for the last 20 mins of the flight, the announcement indicator came on the TV screens and took them over, even though no announcement was being made. Really disappointed.

Crew was great. Near on time departure and early arrival. Snacks are always meh. Not a fan of the "pay for everything including miles " proposal unless base flight rate going to be 100 bucks.

On the return flight, flight attendant Britt went out of her way to inform passengers that several of us had tight connections.

Too many people are taking up space in the overhead bins with their extra piece of luggage. Since they cannot fit their backpacks or extra luggage piece under the seat in front of them, they store it in the overheads and thus taking up room for other passengers. It wasn’t only one or two persons; more like 12 or 13 passengers.

Kayak botched up the booking, i had to call delta and fix. In the process Delta failed to honor my comfort plus seat assignment that i had previously.

For a 4 1/2 hour international flight all we got was 1 small pack of cookies and a drink. You had to watch movies on your own devise.

The seats need better cushioning for a nearly 5-hour flight, it was a bit uncomfortable. I'm glad American has free wi-fi but there were was a bout 30 minutes in the middle of the flight when there was no connection which was frustrating.

My original flight got delayed day of so I had to rebook it from one layover to two layovers. The flight also left earlier which was a slight inconvenience but manageable. Then my first connection flight got delayed 3 separate times for a total of 2 hours delayed, causing me to miss my second connection flight back to Santa Barbara. Now, because of this missed flight, I am missing my college classes that I pay for.

Flight: Started on time. Comfortable flight. Arrived on time. Crew: Very cordial and helpful. Drinks and snack was served with a smile. Overall enjoyed the trip. Regards, Hari Doss Chanchala Doss

I’m sure Business Class would be excellent. I feel like I got what I paid for. Overall it was good and well worth it. I would do it again.

This short sector between Miami and JFK was undertaken purely for business purposes, with efficiency as the primary objective rather than a full inflight experience. Overall, the journey met its intended purpose; however, the ground experience at Miami stood out significantly. During check-in, I was unable to link my frequent flyer details from Qatar Airways (oneworld alliance) through either the self-service kiosk or web check-in. The situation was handled exceptionally well by the check-in agent, who demonstrated remarkable ownership. She coordinated across multiple counters, ensured my frequent flyer number was correctly reflected, reissued the boarding pass, and confirmed that mileage accrual would be recognized. Additionally, she ensured the boarding pass reflected priority status, enabling a seamless priority check-in experience without delays. This level of proactive service was both commendable and impactful. Boarding and the inflight experience, operated by American Airlines under a codeshare arrangement, were efficient but largely transactional. While operational delivery was smooth, there was no visible recognition of oneworld frequent flyer status onboard. In comparison to the consistently personalized engagement typically experienced with Qatar Airways, this absence was noticeable—though understandably a potential limitation of codeshare alignment rather than a direct service shortfall. In summary, while the flight itself fulfilled its operational intent, the exceptional professionalism and commitment demonstrated at the Miami check-in counter was the defining highlight of this journey. Greater consistency in elite recognition across partner airlines would further enhance the overall experience.

Business class was very good, one of my best flights

Incredibly delayed. First delay was due to plane coming in being late. Resulted in 30 minute delay. Boarded and then had multiple mechanical issues. Was on plane for an hour until they told people they could get off if they wanted but couldn't come back. Then gate agent rushed in and said they had lost control of who went off and we would all have to deplane and then get back on. They said flight had not been cancelled. Then while sitting waiting to board again they announced it would take two hours to get new plane and to wait at new gate. New plane arrived, reboarded only to find out that pilots had timed out. Waited for new pilots. In that time one of the flight attendants timed out. Never received food or water while waiting. Was confusing mess as to what was happening. Even flight attendants and gate agents were getting frustrated. Almost 6 hours delayed. Called American to received flight credit but can't get anywhere as Kayak reservation and don't have a ticket number. Reached out to Kayak but never heard back.

The new planes (American Eagle) are beautiful and especially comfortable. The flight attendants are consistently professional and courteous. And, while it may seem inconsequential, the new liquid tube of coffee creamer—in contrast to the powdered coffee creamer—makes all the difference in a cup of coffee.

Flight was delayed and they gave up my seat on my connection, even when I could still make the flight

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

Information on your arrival and departure airports