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Simpson Bay

$318+ Cheap flights from Madison (MSN) 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 12/12. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — SXM
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
1 adult, Economy
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Find 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 October 30, 2025.

This American Airlines deal was found by Cheapflights users on 10/30. 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 12/128:08 pmMSN - SXM
1 stop17h 00mAmerican Airlines
Wed 12/172:51 pmSXM - MSN
1 stop10h 49mAmerican Airlines
Deal found 10/30$612
This American Airlines deal was found by Cheapflights users on 10/30. 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 12/143:55 pmMSN - SXM
2 stops20h 25mAmerican Airlines
Sun 12/212:59 pmSXM - MSN
1 stop11h 00mAmerican Airlines
Deal found 10/30$622
This American Airlines deal was found by Cheapflights users on 10/30. 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 11/297:07 amMSN - SXM
1 stop28h 53mAmerican Airlines
Sat 12/64:00 pmSXM - MSN
1 stop9h 29mAmerican Airlines
Deal found 10/30$623
This American Airlines deal was found by Cheapflights users on 10/29. 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 12/1111:19 amMSN - SXM
1 stop24h 33mAmerican Airlines
Tue 12/163:20 pmSXM - MSN
2 stops20h 56mAmerican Airlines
Deal found 10/29$628
This Delta deal was found by Cheapflights users on 10/30. 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 12/115:38 amMSN - SXM
1 stop6h 50mDelta
Tue 12/163:53 pmSXM - MSN
1 stop8h 33mDelta
Deal found 10/30$651
This American Airlines deal was found by Cheapflights users on 10/29. 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 12/54:02 pmMSN - SXM
2 stops18h 08mAmerican Airlines
Wed 12/105:25 pmSXM - MSN
2 stops19h 06mAmerican Airlines
Deal found 10/29$656
This Delta deal was found by Cheapflights users on 10/29. 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 11/105:29 amMSN - SXM
1 stop7h 26mDelta
Fri 11/144:20 pmSXM - MSN
1 stop8h 12mDelta
Deal found 10/29$875
This American Airlines deal was found by Cheapflights users on 10/29. 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 11/103:59 pmMSN - SXM
2 stops20h 20mAmerican Airlines
Fri 11/143:20 pmSXM - MSN
2 stops19h 58mAmerican Airlines
Deal found 10/29$880
This Mytrip deal was found by Cheapflights users on 10/30. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/141:10 pmMSN - SXM
3 stops23h 05mMultiple Airlines
Sun 12/213:40 pmSXM - MSN
3 stops24h 46mMultiple Airlines
Deal found 10/30$1,058

Cheap 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 October 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$587
(Delta)

One-way from

$318
(Delta)

Popular in

February

Cheapest in

July

Average price

$587
Provider with most accurate pricing for Madison Truax Field-Simpson Bay Princess Juliana flight deals.
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Provider most trusted by Cheapflights users for Madison Truax Field-Simpson Bay Princess Juliana flights.
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From Madison Truax Field to Simpson Bay Princess Juliana
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One-way flight from Madison Truax Field to Simpson Bay Princess Juliana
Search Deals
Highest demand for flights based on searches. 21% potential increase in price ($200 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($40 potential savings vs. average RT price).
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Average for round-trip flights in October 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 October 30, 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

Tue 4/28

5:45 am-2:09 pm

1 stop7h 24m

Simpson Bay Princess Juliana

Wed 5/13

3:20 pm-10:35 pm

1 stop8h 15m

$587

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Sun 4/26

5:45 am-2:09 pm

1 stop7h 24m

Simpson Bay Princess Juliana

Tue 5/12

3:20 pm-10:35 pm

1 stop8h 15m

$587

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Sun 4/26

5:45 am-2:09 pm

1 stop7h 24m

Simpson Bay Princess Juliana

Wed 5/13

3:20 pm-10:35 pm

1 stop8h 15m

$587

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Tue 4/28

5:45 am-2:09 pm

1 stop7h 24m

Simpson Bay Princess Juliana

Tue 5/12

3:20 pm-10:35 pm

1 stop8h 15m

$587

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Tue 4/28

5:45 am-2:09 pm

1 stop7h 24m

Simpson Bay Princess Juliana

Thu 5/14

3:20 pm-12:54 pm

2 stops22h 34m

$592

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Mon 4/27

1:45 pm-2:09 pm

2 stops23h 24m

Simpson Bay Princess Juliana

Wed 5/13

3:20 pm-10:35 pm

1 stop8h 15m

$592

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Mon 4/27

5:50 pm-12:18 pm

2 stops17h 28m

Simpson Bay Princess Juliana

Tue 5/12

3:20 pm-10:35 pm

1 stop8h 15m

$592

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Sun 4/26

2:40 pm-12:18 pm

2 stops20h 38m

Simpson Bay Princess Juliana

Thu 5/14

3:20 pm-12:54 pm

2 stops22h 34m

$592

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Thu 12/11

4:39 pm-1:52 pm

2 stops19h 13m

$318

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Thu 12/11

5:38 am-2:28 pm

1 stop6h 50m

$318

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/29

Showing 1-10 of 13 results
1
2

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 October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
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 eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Madison-Simpson Bay flight deals on Cheapflights vs. eDreams >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 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 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, January is the cheapest month in which you can book a flight from Madison to Simpson Bay (average of $566). Flying from Madison to Simpson Bay in August is currently the most expensive (average of $712). 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 October 30, 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 October 30, 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
7,998 reviews

Overall

7.9

Boarding

8.2

Entertainment

7.9

Crew

8.5

Comfort

7.9

Food

7.3

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
Delta
7.9
Good
7,998 reviews
Delta
7.9
Good
7,998 reviews

Overall

7.9

Boarding

8.2

Entertainment

7.9

Crew

8.5

Comfort

7.9

Food

7.3

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.

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 fly from Madison to Simpson Bay in about 7h 24m. The time it takes to get you to your destination can typically vary by up to . Madison and Simpson Bay are separated by a distance of 2311 mi.

  • 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 21% 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, January is the cheapest month in which you can book a flight from Madison to Simpson Bay (average of $566). Flying from Madison to Simpson Bay in August is currently the most expensive (average of $712). 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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$587Average$645FlexibilityNo cancel feeOn-timeN/A

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