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Simpson Bay

$633+ Cheap flights from Greensboro (GSO) 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 12/4. Fares are subject to change and may not be available on all flights or dates of travel.
GSO — SXM
Nov 27 — Dec 41
Thu 11/27
Thu 12/4
1 adult, Economy
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Cheap flight deals from Greensboro to Simpson Bay

Discover tips and strategies to find the most affordable flight options for your journey from Greensboro (GSO) 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 October 28, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$633
(American Airlines)

Popular in

November

Cheapest in

December

Average price

$713
Provider with most accurate pricing for Greensboro/H. Point-Simpson Bay Princess Juliana flight deals.
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Provider most trusted by Cheapflights users for Greensboro/H. Point-Simpson Bay Princess Juliana flights.
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From Greensboro/H. Point to Simpson Bay Princess Juliana
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Highest demand for flights based on searches. 5% potential increase in price ($43 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($39 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Find flight deals from Greensboro to Simpson Bay

Cheapest flights from Greensboro to Simpson Bay
Explore the most affordable flight options available from Greensboro to Simpson Bay. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 28, 2025.

This American Airlines deal was found by Cheapflights users on 10/26. 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 12/48:20 pmGSO - SXM
2 stops17h 00mAmerican Airlines
Mon 12/82:51 pmSXM - GSO
2 stops20h 13mAmerican Airlines
Deal found 10/26$633
This American Airlines deal was found by Cheapflights users on 10/27. 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 12/56:55 pmGSO - SXM
2 stops16h 15mAmerican Airlines
Mon 12/85:25 pmSXM - GSO
2 stops19h 12mAmerican Airlines
Deal found 10/27$654
This United Airlines deal was found by Cheapflights users on 10/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/136:00 amGSO - SXM
1 stop6h 50mUnited Airlines
Sun 11/163:00 pmSXM - GSO
1 stop30h 45mUnited Airlines
Deal found 10/28$656
This United Airlines deal was found by Cheapflights users on 10/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/126:05 amGSO - SXM
1 stop6h 45mUnited Airlines
Sun 11/163:00 pmSXM - GSO
1 stop30h 45mUnited Airlines
Deal found 10/28$688
This United Airlines deal was found by Cheapflights users on 10/26. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/306:00 amGSO - SXM
1 stop6h 50mUnited Airlines
Sat 11/14:00 pmSXM - GSO
1 stop23h 13mUnited Airlines
Deal found 10/26$952
This American Airlines deal was found by Cheapflights users on 10/26. 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 10/307:15 pmGSO - SXM
2 stops18h 22mAmerican Airlines
Sat 11/14:24 pmSXM - GSO
2 stops19h 25mAmerican Airlines
Deal found 10/26$1,014
This Delta deal was found by Cheapflights users on 10/28. 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.
Thu 11/136:55 pmGSO - SXM
2 stops42h 10mDelta
Sun 11/164:20 pmSXM - GSO
1 stop7h 20mDelta
Deal found 10/28$1,514
This WestJet deal was found by Cheapflights users on 10/28. 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.
Wed 11/124:01 pmGSO - SXM
2 stops22h 20mWestJet
Sun 11/164:20 pmSXM - GSO
2 stops32h 33mWestJet
Deal found 10/28$3,863
This WestJet deal was found by Cheapflights users on 10/28. 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 11/135:07 pmGSO - SXM
2 stops21h 14mWestJet
Sun 11/164:20 pmSXM - GSO
2 stops26h 30mWestJet
Deal found 10/28$3,918

Cheapflights Fare Finder

 
Customize your flight search to find flights from Greensboro 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 October 28, 2025.
Use the filters below to find and compare flights from Greensboro to Simpson Bay that are best for you.

Fly from

Greensboro

Fly to

Simpson Bay

Route

Depart

Return

Price

GreensboroSimpson Bay

GSO - SXM

GSOSXM

Greensboro/H. Point

Thu 12/4

8:20 pm-2:20 pm

2 stops17h 00m

Simpson Bay Princess Juliana

Mon 12/8

2:51 pm-10:04 am

2 stops20h 13m

$633

GreensboroSimpson Bay

GSO - SXM

GSOSXM

Greensboro/H. Point

Fri 12/5

7:10 am-2:20 pm

1 stop6h 10m

Simpson Bay Princess Juliana

Mon 12/8

5:25 pm-9:44 am

2 stops17h 19m

$633

GreensboroSimpson Bay

GSO - SXM

GSOSXM

Greensboro/H. Point

Thu 11/13

6:00 am-1:50 pm

1 stop6h 50m

Simpson Bay Princess Juliana

Sun 11/16

3:00 pm-8:45 pm

1 stop30h 45m

$656

GreensboroSimpson Bay

GSO - SXM

GSOSXM

Greensboro/H. Point

Wed 11/12

6:05 am-1:50 pm

1 stop6h 45m

Simpson Bay Princess Juliana

Sun 11/16

3:00 pm-8:45 pm

1 stop30h 45m

$688

GreensboroSimpson Bay

GSO - SXM

GSOSXM

Greensboro/H. Point

Thu 11/13

6:55 pm-2:05 pm

2 stops42h 10m

Simpson Bay Princess Juliana

Sun 11/16

4:20 pm-10:40 pm

1 stop7h 20m

$1,514

GreensboroSimpson Bay

GSO - SXM

GSOSXM

Greensboro/H. Point

Wed 11/12

4:01 pm-3:21 pm

2 stops22h 20m

Simpson Bay Princess Juliana

Sun 11/16

4:20 pm-11:53 pm

2 stops32h 33m

$3,863

GreensboroSimpson Bay

GSO - SXM

GSOSXM

Greensboro/H. Point

Thu 11/13

5:07 pm-3:21 pm

2 stops21h 14m

Simpson Bay Princess Juliana

Sun 11/16

4:20 pm-5:50 pm

2 stops26h 30m

$3,918

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/26

Compare providers for flights from Greensboro 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 Greensboro to Simpson Bay in October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 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 Greensboro-Simpson Bay flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Greensboro-Simpson Bay flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Greensboro-Simpson Bay flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Greensboro-Simpson Bay flights, Cheapflights users trust eDreams the most. eDreams 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 Greensboro-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 Greensboro to Simpson Bay

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

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

Currently, August is the cheapest month in which you can book a flight from Greensboro to Simpson Bay (average of $247). Flying from Greensboro to Simpson Bay in February is currently the most expensive (average of $469). 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 October 28, 2025.
See what other customers who have flown with American Airlines from Greensboro 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
11,032 reviews

Crew

8.0

Boarding

7.5

Overall

7.2

Comfort

7.2

Food

6.4

Entertainment

6.9

Reviews

1 / 20
2.0
Mediocre

Jeremy,Sep 2025

SAN - PHL

Terrible. Bad customer service and unacceptable delay on the tarmac
American Airlines
7.2
Good
11,032 reviews
American Airlines
7.2
Good
11,032 reviews

Crew

8.0

Boarding

7.5

Overall

7.2

Comfort

7.2

Food

6.4

Entertainment

6.9

Reviews

1 / 20
2.0
Mediocre

Jeremy,Sep 2025

SAN - PHL

Terrible. Bad customer service and unacceptable delay on the tarmac

Related info for your journey

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

    For as low as $633, American Airlines can have you in Simpson Bay from Greensboro in 17h. Greensboro and Simpson Bay are separated by a distance of 1615 mi.

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

    According to our current data, American Airlines ($561), offers the cheapest pricing from Greensboro to Simpson Bay. Users have found that American Airlines is 23% cheaper than the other options available to this destination.

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

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

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

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

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

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

    Currently, August is the cheapest month in which you can book a flight from Greensboro to Simpson Bay (average of $247). Flying from Greensboro to Simpson Bay in February is currently the most expensive (average of $469). 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 Greensboro to Simpson Bay

Discover the top airline that operate flights from Greensboro 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 October 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$561Average$713FlexibilityNo cancel feeOn-time71%

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