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Simpson Bay

$613+ Cheap flights from Madison (MSN) 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 2/23. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — SXM
Feb 27 — Mar 61
Fri 2/27
Fri 3/6
1 adult, Economy
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Cheap flight deals from Madison to Simpson Bay

Cheapest flights from Madison to Simpson Bay
Explore the most affordable flight options available from Madison to Simpson Bay. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 28, 2026.

This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/235:54 pm
MSN
-
SXM
2 stops16h 19m
Delta
Tue 3/34:15 pm
SXM
-
MSN
2 stops20h 34m
Delta
Deal found 1/26$613
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/95:44 pm
MSN
-
SXM
1 stop18h 01m
American Airlines
Wed 6/241:45 pm
SXM
-
MSN
1 stop9h 28m
American Airlines
Deal found 1/27$615
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/318:25 pm
MSN
-
SXM
2 stops18h 55m
American Airlines
Sat 11/73:20 pm
SXM
-
MSN
2 stops20h 01m
American Airlines
Deal found 1/27$645
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.
Tue 5/53:16 pm
MSN
-
SXM
2 stops21h 05m
American Airlines
Sun 5/104:35 pm
SXM
-
MSN
2 stops18h 00m
American Airlines
Deal found 1/26$650
This Flysmarter 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 Flysmarter is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/233:11 pm
MSN
-
SXM
2 stops21h 08m
British Airways
Tue 3/34:01 pm
SXM
-
MSN
1 stop19h 52m
British Airways
Deal found 1/26$737
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.
Sat 4/258:30 am
MSN
-
SXM
1 stop7h 19m
United Airlines
Wed 4/291:35 pm
SXM
-
MSN
2 stops20h 01m
United Airlines
Deal found 1/25$755
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/74:30 pm
MSN
-
SXM
2 stops21h 58m
American Airlines
Sat 2/213:00 pm
SXM
-
MSN
1 stop8h 14m
American Airlines
Deal found 1/27$850

Find flight deals from Madison to Simpson Bay

Discover tips and strategies to find the most affordable flight options for your journey from Madison (MSN) 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

$613
(Delta)
Provider with most accurate pricing for Madison Truax Field-Simpson Bay Princess Juliana flight deals.
Search Deals
Provider most trusted by Cheapflights users for Madison Truax Field-Simpson Bay Princess Juliana flights.
Search Deals
From Madison Truax Field to Simpson Bay Princess Juliana
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Madison 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 Madison to Simpson Bay that are best for you.

Fly from

Madison

Fly to

Simpson Bay

Route

Depart

Return

Price

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Mon 2/23

5:54 pm-12:13 pm

2 stops16h 19m

Simpson Bay Princess Juliana

Tue 3/3

4:15 pm-10:49 am

2 stops20h 34m

$613

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Tue 6/9

5:44 pm-12:45 pm

1 stop18h 01m

Simpson Bay Princess Juliana

Wed 6/24

1:45 pm-10:13 pm

1 stop9h 28m

$615

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Tue 5/5

3:16 pm-1:21 pm

2 stops21h 05m

Simpson Bay Princess Juliana

Sun 5/10

4:35 pm-9:35 am

2 stops18h 00m

$650

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Mon 2/23

3:11 pm-2:19 pm

2 stops21h 08m

Simpson Bay Princess Juliana

Tue 3/3

4:01 pm-9:53 am

1 stop19h 52m

$737

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/26

Compare providers for flights from Madison 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 Madison to Simpson Bay in January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy2 starsTrust Score*2 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 Madison-Simpson Bay flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Madison-Simpson Bay flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Madison-Simpson Bay flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Madison-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 Madison-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 Madison to Simpson Bay

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

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

Currently, February is the cheapest month in which you can book a flight from Madison to Simpson Bay (average of $577). Flying from Madison to Simpson Bay in June is currently the most expensive (average of $754). 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.

Related info for your journey

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

    Airlines like Delta and American Airlines fly from Madison to Simpson Bay in about 16h 19m. The time it takes to get you to your destination can typically vary by up to 1h 42m. Madison and Simpson Bay are separated by a distance of 2311 mi. This flight may include one or multiple stops.

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

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

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

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

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

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

    Currently, February is the cheapest month in which you can book a flight from Madison to Simpson Bay (average of $577). Flying from Madison to Simpson Bay in June is currently the most expensive (average of $754). 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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