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Simpson Bay

$582+ Cheap flights from Gainesville (GNV) 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 10/13. Fares are subject to change and may not be available on all flights or dates of travel.
GNV — SXM
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
1 adult, Economy
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Cheap flight deals from Gainesville to Simpson Bay

Discover tips and strategies to find the most affordable flight options for your journey from Gainesville (GNV) 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 17, 2025.

Round-trip from

$582
(American Airlines)
From Gainesville Regional to Simpson Bay Princess Juliana
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Find flight deals from Gainesville to Simpson Bay

Cheapest flights from Gainesville to Simpson Bay
Explore the most affordable flight options available from Gainesville to Simpson Bay. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 17, 2025.

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 10/136:00 amGNV - SXM
1 stop7h 37mAmerican Airlines
Mon 10/204:24 pmSXM - GNV
1 stop7h 31mAmerican Airlines
Deal found 9/14$582
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.
Fri 10/176:00 amGNV - SXM
1 stop7h 37mAmerican Airlines
Mon 10/204:24 pmSXM - GNV
1 stop7h 31mAmerican Airlines
Deal found 9/14$607
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.
Fri 10/174:46 pmGNV - SXM
2 stops20h 51mAmerican Airlines
Fri 10/244:24 pmSXM - GNV
2 stops23h 57mAmerican Airlines
Deal found 9/14$648
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.
Wed 10/14:24 pmGNV - SXM
2 stops20h 55mAmerican Airlines
Mon 10/204:24 pmSXM - GNV
2 stops21h 55mAmerican Airlines
Deal found 9/14$880
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/16:00 amGNV - SXM
1 stop7h 50mDelta
Mon 10/203:14 pmSXM - GNV
1 stop7h 21mDelta
Deal found 9/14$1,155

Cheapflights Fare Finder

 
Customize your flight search to find flights from Gainesville 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 17, 2025.
Use the filters below to find and compare flights from Gainesville to Simpson Bay that are best for you.

Fly from

Gainesville

Fly to

Simpson Bay

Route

Depart

Return

Price

GainesvilleSimpson Bay

GNV - SXM

GNVSXM

Gainesville Regional

Fri 10/17

6:00 am-1:37 pm

1 stop7h 37m

Simpson Bay Princess Juliana

Fri 10/24

2:40 pm-11:55 pm

1 stop9h 15m

$582

GainesvilleSimpson Bay

GNV - SXM

GNVSXM

Gainesville Regional

Mon 10/13

9:21 am-1:37 pm

2 stops28h 16m

Simpson Bay Princess Juliana

Mon 10/20

4:24 pm-3:50 pm

2 stops23h 26m

$587

GainesvilleSimpson Bay

GNV - SXM

GNVSXM

Gainesville Regional

Fri 10/17

6:00 am-1:37 pm

1 stop7h 37m

Simpson Bay Princess Juliana

Mon 10/20

4:24 pm-11:55 pm

1 stop7h 31m

$607

GainesvilleSimpson Bay

GNV - SXM

GNVSXM

Gainesville Regional

Wed 10/1

7:25 am-1:19 pm

2 stops29h 54m

Simpson Bay Princess Juliana

Mon 10/20

4:24 pm-11:55 pm

1 stop7h 31m

$880

GainesvilleSimpson Bay

GNV - SXM

GNVSXM

Gainesville Regional

Wed 10/1

6:00 am-1:50 pm

1 stop7h 50m

Simpson Bay Princess Juliana

Mon 10/20

3:14 pm-10:35 pm

1 stop7h 21m

$1,155

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Best time to book a flight from Gainesville to Simpson Bay

Have a flexible travel schedule? Discover the best time to fly to Simpson Bay from Gainesville 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 Gainesville to Simpson Bay

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

Currently, September is the cheapest month in which you can book a flight from Gainesville to Simpson Bay (average of $459). Flying from Gainesville 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.

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 17, 2025.
See what other customers who have flown with American Airlines from Gainesville to Simpson Bay have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.2
Good
10,000 reviews

Overall

7.2

Boarding

7.5

Crew

8.0

Comfort

7.2

Food

6.4

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

Overall

7.2

Boarding

7.5

Crew

8.0

Comfort

7.2

Food

6.4

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 Gainesville 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 Gainesville to Simpson Bay?

    For as low as $582, American Airlines can have you in Simpson Bay from Gainesville in 7h 37m. Airlines will cover a distance of 1449 mi.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Gainesville 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 Gainesville to Simpson Bay?

    Currently, September is the cheapest month in which you can book a flight from Gainesville to Simpson Bay (average of $459). Flying from Gainesville 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 airline flying from Gainesville to Simpson Bay

Discover the top airline that operate flights from Gainesville 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 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$511Average$671FlexibilityNo cancel feeOn-time71%

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