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Simpson Bay

$536+ 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 2/6. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — SXM
Jan 14 — Jan 211
Wed 1/14
Wed 1/21
1 adult, Economy
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Cheap flight deals from Madison to Simpson Bay

Best flights from Madison to Simpson Bay
Discover carefully curated flight deals from Madison to Simpson Bay that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated December 15, 2025.

This United Airlines deal was found by Cheapflights users on 12/13. 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.
Fri 2/62:56 pmMSN - SXM
2 stops20h 54mUnited Airlines
Wed 2/112:52 pmSXM - MSN
1 stop10h 52mUnited Airlines
Deal found 12/13$536
This American Airlines deal was found by Cheapflights users on 12/15. 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 2/24:30 pmMSN - SXM
2 stops20h 01mAmerican Airlines
Mon 2/94:24 pmSXM - MSN
2 stops20h 31mAmerican Airlines
Deal found 12/15$536
This American Airlines deal was found by Cheapflights users on 12/15. 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 2/93:09 pmMSN - SXM
2 stops21h 22mAmerican Airlines
Mon 2/161:41 pmSXM - MSN
2 stops22h 16mAmerican Airlines
Deal found 12/15$536
This American Airlines deal was found by Cheapflights users on 12/13. 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 2/64:47 pmMSN - SXM
2 stops19h 44mAmerican Airlines
Wed 2/113:09 pmSXM - MSN
2 stops20h 06mAmerican Airlines
Deal found 12/13$536
This American Airlines deal was found by Cheapflights users on 12/15. 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 1/143:09 pmMSN - SXM
2 stops19h 49mAmerican Airlines
Wed 1/213:09 pmSXM - MSN
1 stop10h 38mAmerican Airlines
Deal found 12/15$574
This American Airlines deal was found by Cheapflights users on 12/13. 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 2/253:20 pmMSN - SXM
2 stops19h 18mAmerican Airlines
Wed 3/44:40 pmSXM - MSN
1 stop8h 17mAmerican Airlines
Deal found 12/13$579
This American Airlines deal was found by Cheapflights users on 12/15. 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 3/33:20 pmMSN - SXM
2 stops21h 00mAmerican Airlines
Tue 3/103:01 pmSXM - MSN
1 stop8h 55mAmerican Airlines
Deal found 12/15$592

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 December 15, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$536
(United Airlines)

Popular in

February

Cheapest in

July

Average price

$726
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
Highest demand for flights based on searches. 31% potential increase in price ($375 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 8% potential price decrease ($66 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
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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 December 15, 2025.
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

Fri 2/6

2:56 pm-1:50 pm

2 stops20h 54m

Simpson Bay Princess Juliana

Wed 2/11

2:52 pm-11:44 pm

1 stop10h 52m

$536

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Mon 2/2

4:30 pm-2:31 pm

2 stops20h 01m

Simpson Bay Princess Juliana

Mon 2/9

4:24 pm-10:55 am

2 stops20h 31m

$536

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Mon 2/9

3:09 pm-2:31 pm

2 stops21h 22m

Simpson Bay Princess Juliana

Mon 2/16

1:41 pm-9:57 am

2 stops22h 16m

$536

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Fri 2/6

4:47 pm-2:31 pm

2 stops19h 44m

Simpson Bay Princess Juliana

Wed 2/11

3:09 pm-9:15 am

2 stops20h 06m

$536

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Wed 1/14

3:09 pm-12:58 pm

2 stops19h 49m

Simpson Bay Princess Juliana

Wed 1/21

3:09 pm-11:47 pm

1 stop10h 38m

$574

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Wed 2/25

3:20 pm-12:38 pm

2 stops19h 18m

Simpson Bay Princess Juliana

Wed 3/4

4:40 pm-10:57 pm

1 stop8h 17m

$579

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Tue 3/3

3:20 pm-2:20 pm

2 stops21h 00m

Simpson Bay Princess Juliana

Tue 3/10

3:01 pm-10:56 pm

1 stop8h 55m

$592

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/13

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 December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
AranGrantPrice Accuracy2 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 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 Expedia the most. Expedia 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, March is the cheapest month in which you can book a flight from Madison to Simpson Bay (average of $584). Flying from Madison to Simpson Bay in November is currently the most expensive (average of $649). 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.

What is the cheapest time of day to fly from MSN to SXM?

Find hourly flight availability from Madison to Simpson Bay. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 15, 2025.

It’s typically best to fly out from Madison to Simpson Bay at noon. Doing so could potentially save you 45% on the flight price compared to flying in the evening, which is usually more expensive.

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 December 15, 2025.
See what other customers who have flown with Delta from Madison 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.
Delta
7.9
Good
8,008 reviews

Crew

8.5

Boarding

8.1

Overall

7.9

Entertainment

7.9

Comfort

7.9

Food

7.3

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Delta
7.9
Good
8,008 reviews
Delta
7.9
Good
8,008 reviews

Crew

8.5

Boarding

8.1

Overall

7.9

Entertainment

7.9

Comfort

7.9

Food

7.3

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

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 United Airlines and American Airlines fly from Madison to Simpson Bay in about 20h 01m. The time it takes to get you to your destination can typically vary by up to 53m. Madison and Simpson Bay are separated by a distance of 2311 mi. This flight may include one or multiple stops.

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

    According to our current data, Delta ($587), offers the cheapest pricing from Madison to Simpson Bay. You may be able to fly from Madison to Simpson Bay for 28% less than the average price by searching for this airline.

  • 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, March is the cheapest month in which you can book a flight from Madison to Simpson Bay (average of $584). Flying from Madison to Simpson Bay in November is currently the most expensive (average of $649). 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 Madison to Simpson Bay

Discover the top airline that operate flights from Madison 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 December 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$587Average$652FlexibilityNo cancel feeOn-timeN/A

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