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Simpson Bay

$622+ 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 11/20. Fares are subject to change and may not be available on all flights or dates of travel.
TLH — SXM
Aug 23 — Aug 301
Sat 8/23
Sat 8/30
1 adult, Economy
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Cheap 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 August 18, 2025.

Round-trip from

$622
(American Airlines)
From Tallahassee to Simpson Bay Princess Juliana
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Find 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 August 18, 2025.

This American Airlines deal was found by Cheapflights users on 8/16. 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.
Thu 11/209:56 amTLH - SXM
1 stop5h 24mAmerican Airlines
Thu 11/273:30 pmSXM - TLH
1 stop9h 28mAmerican Airlines
Deal found 8/16$622
This American Airlines deal was found by Cheapflights users on 8/16. 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 8/186:20 amTLH - SXM
1 stop8h 49mAmerican Airlines
Sat 8/232:15 pmSXM - TLH
1 stop8h 30mAmerican Airlines
Deal found 8/16$862
This American Airlines deal was found by Cheapflights users on 8/17. 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.
Sat 11/228:04 pmTLH - SXM
2 stops19h 16mAmerican Airlines
Sat 11/295:24 pmSXM - TLH
2 stops21h 04mAmerican Airlines
Deal found 8/17$1,262
This American Airlines deal was found by Cheapflights users on 8/17. 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 11/216:13 amTLH - SXM
1 stop6h 47mAmerican Airlines
Sun 11/303:20 pmSXM - TLH
2 stops21h 18mAmerican Airlines
Deal found 8/17$1,326

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 August 18, 2025.
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

Thu 11/20

9:56 am-4:20 pm

1 stop5h 24m

Simpson Bay Princess Juliana

Thu 11/27

3:30 pm-11:58 pm

1 stop9h 28m

$622

TallahasseeSimpson Bay

TLH - SXM

TLHSXM

Tallahassee

Sat 11/22

8:04 pm-4:20 pm

2 stops19h 16m

Simpson Bay Princess Juliana

Sat 11/29

5:24 pm-1:28 pm

2 stops21h 04m

$1,262

TallahasseeSimpson Bay

TLH - SXM

TLHSXM

Tallahassee

Fri 11/21

6:13 am-2:00 pm

1 stop6h 47m

Simpson Bay Princess Juliana

Sun 11/30

3:20 pm-11:38 am

2 stops21h 18m

$1,326

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/16

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 August 18, 2025.
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
10,000 reviews

Crew

8.0

Food

6.5

Overall

7.2

Comfort

7.2

Boarding

7.5

Entertainment

6.9

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

MIA - DCA

Flight delayed 5 hours and was told it was due to mechanical issues. Instead of providing lodging due to missed connecting flight, American changed the cause of delay to weather, which meant they were not able required to provide a hotel. To make matters worse, one of our checked bags was lost even though its status said it was “by the plane” but no one at the service desk seemed able to locate it.
American Airlines
7.2
Good
10,000 reviews
American Airlines
7.2
Good
10,000 reviews

Crew

8.0

Food

6.5

Overall

7.2

Comfort

7.2

Boarding

7.5

Entertainment

6.9

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

MIA - DCA

Flight delayed 5 hours and was told it was due to mechanical issues. Instead of providing lodging due to missed connecting flight, American changed the cause of delay to weather, which meant they were not able required to provide a hotel. To make matters worse, one of our checked bags was lost even though its status said it was “by the plane” but no one at the service desk seemed able to locate it.

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.

  • 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 $496.

  • 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.

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

    Currently, September is the cheapest month in which you can book a flight from Tallahassee to Simpson Bay (average of $459). Flying from Tallahassee to Simpson Bay in March is currently the most expensive (average of $654). 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 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 August 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$496Average$673FlexibilityNo cancel feeOn-time71%

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