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Simpson Bay

$108+ Cheap flights from Greensboro (GSO) to Simpson Bay (SXM)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 3/22. Fares are subject to change and may not be available on all flights or dates of travel.
GSO — SXM
Feb 27 — Mar 61
Fri 2/27
Fri 3/6
1 adult, Economy
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Cheap 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 January 28, 2026.

This United Airlines deal was found by Cheapflights users on 1/26. 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.
Mon 3/237:35 pm
GSO
-
SXM
1 stop17h 15m
United Airlines
Mon 3/303:50 pm
SXM
-
GSO
1 stop7h 54m
United Airlines
Deal found 1/26$305
This United Airlines deal was found by Cheapflights users on 1/26. 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 3/126:00 am
GSO
-
SXM
1 stop8h 51m
United Airlines
Thu 3/193:55 pm
SXM
-
GSO
1 stop27h 05m
United Airlines
Deal found 1/26$367
This United Airlines deal was found by Cheapflights users on 1/27. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/72:46 pm
GSO
-
SXM
1 stop22h 04m
United Airlines
Wed 2/112:52 pm
SXM
-
GSO
1 stop9h 11m
United Airlines
Deal found 1/27$394
This United Airlines deal was found by Cheapflights users on 1/26. 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.
Sat 5/96:15 am
GSO
-
SXM
1 stop8h 28m
United Airlines
Sat 5/163:50 pm
SXM
-
GSO
1 stop7h 54m
United Airlines
Deal found 1/26$409
This United Airlines deal was found by Cheapflights users on 1/26. 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.
Tue 3/106:00 am
GSO
-
SXM
1 stop8h 51m
United Airlines
Fri 3/133:55 pm
SXM
-
GSO
1 stop27h 05m
United Airlines
Deal found 1/26$421
This United Airlines deal was found by Cheapflights users on 1/27. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/256:00 am
GSO
-
SXM
1 stop6h 27m
United Airlines
Sat 5/23:50 pm
SXM
-
GSO
1 stop7h 54m
United Airlines
Deal found 1/27$435
This United Airlines deal was found by Cheapflights users on 1/25. 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.
Mon 3/26:00 am
GSO
-
SXM
1 stop6h 50m
United Airlines
Mon 3/233:55 pm
SXM
-
GSO
1 stop22h 18m
United Airlines
Deal found 1/25$481
This American Airlines deal was found by Cheapflights users on 1/26. 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.
Mon 3/238:41 pm
GSO
-
SXM
1 stop16h 35m
American Airlines
Tue 3/3112:29 pm
SXM
-
GSO
2 stops10h 28m
American Airlines
Deal found 1/26$572
This American Airlines deal was found by Cheapflights users on 1/25. 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 5/105:18 am
GSO
-
SXM
1 stop8h 03m
American Airlines
Sat 5/231:45 pm
SXM
-
GSO
1 stop10h 14m
American Airlines
Deal found 1/25$592
This American Airlines deal was found by Cheapflights users on 1/26. 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.
Mon 3/238:41 pm
GSO
-
SXM
2 stops18h 47m
American Airlines
Mon 3/302:17 pm
SXM
-
GSO
1 stop8h 42m
American Airlines
Deal found 1/26$597
This American Airlines deal was found by Cheapflights users on 1/26. 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.
Sat 5/1611:13 am
GSO
-
SXM
1 stop26h 08m
American Airlines
Sat 5/231:45 pm
SXM
-
GSO
1 stop10h 14m
American Airlines
Deal found 1/26$598
This American Airlines deal was found by Cheapflights users on 1/26. 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.
Sun 5/105:18 am
GSO
-
SXM
1 stop8h 03m
American Airlines
Sun 5/174:35 pm
SXM
-
GSO
2 stops17h 50m
American Airlines
Deal found 1/26$602

Find 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 January 28, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$305
(United Airlines)

One-way from

$108
(United Airlines)
Provider with most accurate pricing for Greensboro/H. Point-Simpson Bay Princess Juliana flight deals.
Search Deals
Provider most trusted by Cheapflights users for Greensboro/H. Point-Simpson Bay Princess Juliana flights.
Search Deals
From Greensboro/H. Point to Simpson Bay Princess Juliana
Search Deals
One-way flight from Greensboro/H. Point to Simpson Bay Princess Juliana
Search Deals

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 January 28, 2026.
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

Mon 3/23

5:19 am-1:54 pm

1 stop8h 35m

Simpson Bay Princess Juliana

Tue 3/31

12:55 pm-11:59 pm

1 stop11h 04m

$305

GreensboroSimpson Bay

GSO - SXM

GSOSXM

Greensboro/H. Point

Mon 3/23

7:35 pm-12:50 pm

1 stop17h 15m

Simpson Bay Princess Juliana

Mon 3/30

3:50 pm-11:44 pm

1 stop7h 54m

$305

GreensboroSimpson Bay

GSO - SXM

GSOSXM

Greensboro/H. Point

Thu 3/12

6:00 am-2:51 pm

1 stop8h 51m

Simpson Bay Princess Juliana

Thu 3/19

3:55 pm-7:00 pm

1 stop27h 05m

$367

GreensboroSimpson Bay

GSO - SXM

GSOSXM

Greensboro/H. Point

Sat 2/7

2:46 pm-1:50 pm

1 stop22h 04m

Simpson Bay Princess Juliana

Wed 2/11

2:52 pm-11:03 pm

1 stop9h 11m

$394

GreensboroSimpson Bay

GSO - SXM

GSOSXM

Greensboro/H. Point

Sat 5/9

6:15 am-2:43 pm

1 stop8h 28m

Simpson Bay Princess Juliana

Sat 5/16

3:50 pm-11:44 pm

1 stop7h 54m

$409

GreensboroSimpson Bay

GSO - SXM

GSOSXM

Greensboro/H. Point

Tue 3/10

6:00 am-2:51 pm

1 stop8h 51m

Simpson Bay Princess Juliana

Fri 3/13

3:55 pm-7:00 pm

1 stop27h 05m

$421

GreensboroSimpson Bay

GSO - SXM

GSOSXM

Greensboro/H. Point

Sat 4/25

6:00 am-12:27 pm

1 stop6h 27m

Simpson Bay Princess Juliana

Sat 5/2

3:50 pm-11:44 pm

1 stop7h 54m

$435

GreensboroSimpson Bay

GSO - SXM

GSOSXM

Greensboro/H. Point

Mon 3/2

6:00 am-1:50 pm

1 stop6h 50m

Simpson Bay Princess Juliana

Mon 3/23

3:55 pm-2:13 pm

1 stop22h 18m

$481

GreensboroSimpson Bay

GSO - SXM

GSOSXM

Greensboro/H. Point

Mon 3/23

5:28 am-3:28 pm

2 stops10h 00m

Simpson Bay Princess Juliana

Tue 3/31

4:28 pm-8:44 am

2 stops16h 16m

$572

GreensboroSimpson Bay

GSO - SXM

GSOSXM

Greensboro/H. Point

Wed 3/25

6:00 am-3:28 pm

2 stops9h 28m

Simpson Bay Princess Juliana

Thu 4/2

12:29 pm-8:44 am

2 stops20h 15m

$572

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/26

Showing 1-10 of 21 results
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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 January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice 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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Greensboro-Simpson Bay flight deals on Cheapflights vs. FlightHub >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 FlightHub the most. FlightHub 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, June is the cheapest month in which you can book a flight from Greensboro to Simpson Bay (average of $240). Flying from Greensboro to Simpson Bay in October is currently the most expensive (average of $417). 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 January 28, 2026.
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
11,201 reviews

Overall

7.2

Food

6.4

Comfort

7.2

Crew

8.0

Boarding

7.5

Entertainment

6.9

Reviews

1 / 20
2.0
Mediocre

Susie,Jan 2026

CLT - TPA

This flight was delayed 3 or 4 times. We had boarded the plane, sat on plane for a good 30 minutes, then we had to board the aircraft, walk to a different gate, wait and then board another aircraft. We arrived in Tampa 4 hours later than the original booking. I feel there should have been some sort of compensation especially for the advantage members.
American Airlines
7.2
Good
11,201 reviews
American Airlines
7.2
Good
11,201 reviews

Overall

7.2

Food

6.4

Comfort

7.2

Crew

8.0

Boarding

7.5

Entertainment

6.9

Reviews

1 / 20
2.0
Mediocre

Susie,Jan 2026

CLT - TPA

This flight was delayed 3 or 4 times. We had boarded the plane, sat on plane for a good 30 minutes, then we had to board the aircraft, walk to a different gate, wait and then board another aircraft. We arrived in Tampa 4 hours later than the original booking. I feel there should have been some sort of compensation especially for the advantage members.

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 $305, Delta can have you in Simpson Bay from Greensboro in 8h 35m. Greensboro and Simpson Bay are separated by a distance of 1615 mi. This flight may include one or multiple stops.

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

    According to our current data, American Airlines ($581), offers the cheapest pricing from Greensboro to Simpson Bay.

  • 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, June is the cheapest month in which you can book a flight from Greensboro to Simpson Bay (average of $240). Flying from Greensboro to Simpson Bay in October is currently the most expensive (average of $417). 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 January 28, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$581Average$713FlexibilityNo cancel feeOn-time71%

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