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Simpson Bay

$572+ Cheap flights from Tallahassee (TLH) to Simpson Bay (SXM)

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 4/5. Fares are subject to change and may not be available on all flights or dates of travel.
TLH — SXM
Feb 22 — Mar 11
Sun 2/22
Sun 3/1
1 adult, Economy
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Cheap flight deals from Tallahassee to Simpson Bay

Cheapest flights from Tallahassee to Simpson Bay
Explore the most affordable flight options available from Tallahassee to Simpson Bay. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 23, 2026.

This American Airlines deal was found by Cheapflights users on 1/22. 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 4/56:10 am
TLH
-
SXM
1 stop9h 18m
American Airlines
Fri 4/104:35 pm
SXM
-
TLH
2 stops20h 26m
American Airlines
Deal found 1/22$572
This American Airlines deal was found by Cheapflights users on 1/22. 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 6/107:47 pm
TLH
-
SXM
2 stops19h 44m
American Airlines
Wed 6/174:36 pm
SXM
-
TLH
1 stop16h 41m
American Airlines
Deal found 1/22$597
This WestJet 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/82:07 pm
TLH
-
SXM
2 stops24h 10m
WestJet
Wed 2/114:20 pm
SXM
-
TLH
2 stops27h 20m
WestJet
Deal found 1/20$3,648

Find flight deals from Tallahassee to Simpson Bay

Discover tips and strategies to find the most affordable flight options for your journey from Tallahassee (TLH) 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 23, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

AranGrant
3 stars

Round-trip from

$572
(American Airlines)
Provider with most accurate pricing for Tallahassee-Simpson Bay Princess Juliana flight deals.
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Provider most trusted by Cheapflights users for Tallahassee-Simpson Bay Princess Juliana flights.
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From Tallahassee to Simpson Bay Princess Juliana
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Tallahassee 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 23, 2026.
Use the filters below to find and compare flights from Tallahassee to Simpson Bay that are best for you.

Fly from

Tallahassee

Fly to

Simpson Bay

Route

Depart

Return

Price

TallahasseeSimpson Bay

TLH - SXM

TLHSXM

Tallahassee

Sun 4/5

8:51 pm-11:29 am

1 stop14h 38m

Simpson Bay Princess Juliana

Fri 4/10

4:35 pm-1:01 pm

2 stops20h 26m

$572

TallahasseeSimpson Bay

TLH - SXM

TLHSXM

Tallahassee

Wed 6/10

7:53 pm-3:31 pm

2 stops19h 38m

Simpson Bay Princess Juliana

Wed 6/17

2:27 pm-11:59 pm

1 stop9h 32m

$597

TallahasseeSimpson Bay

TLH - SXM

TLHSXM

Tallahassee

Sun 2/8

2:07 pm-3:17 pm

2 stops24h 10m

Simpson Bay Princess Juliana

Wed 2/11

4:20 pm-6:40 pm

2 stops27h 20m

$3,648

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/21

Compare providers for flights from Tallahassee 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 Tallahassee to Simpson Bay in January.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*1 star
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 Tallahassee-Simpson Bay flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Tallahassee-Simpson Bay flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Tallahassee-Simpson Bay flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Tallahassee-Simpson Bay flights, Cheapflights users trust AranGrant the most. AranGrant 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 Tallahassee-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 Tallahassee to Simpson Bay

Have a flexible travel schedule? Discover the best time to fly to Simpson Bay from Tallahassee 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 23, 2026.
Get a feel of what it's like to fly with American Airlines from Tallahassee to Simpson Bay by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.2
Good
11,177 reviews

Food

6.4

Overall

7.2

Boarding

7.5

Comfort

7.2

Entertainment

6.9

Crew

8.0

Reviews

1 / 20
4.0
Okay

Susie,Jan 2026

TPA - CLT

I was sitting at the back of the plane and the flight attendants were so loud, talking to each other and laughing! I thought they were having a party back there.
American Airlines
7.2
Good
11,177 reviews
American Airlines
7.2
Good
11,177 reviews

Food

6.4

Overall

7.2

Boarding

7.5

Comfort

7.2

Entertainment

6.9

Crew

8.0

Reviews

1 / 20
4.0
Okay

Susie,Jan 2026

TPA - CLT

I was sitting at the back of the plane and the flight attendants were so loud, talking to each other and laughing! I thought they were having a party back there.

Related info for your journey

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

    A quick flight from Tallahassee to Simpson Bay can take about 14h 38m. American Airlines provides one of the quickest options available for as low as $572. Tallahassee and Simpson Bay are separated by a distance of 1582 mi.

  • What is the cheapest airline to fly from Tallahassee to Simpson Bay round-trip?

    Flying on American Airlines is currently your cheapest option to Simpson Bay, with prices starting at $554.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Tallahassee 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 airline flying from Tallahassee to Simpson Bay

Discover the top airline that operate flights from Tallahassee 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 23, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$554Average$756FlexibilityNo cancel feeOn-time71%

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