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Simpson Bay

$612+ 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 9/12. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — SXM
Aug 4 — Aug 111
Mon 8/4
Mon 8/11
1 adult, Economy
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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 July 30, 2025.

Round-trip from

$612
(Delta)

Popular in

February

Cheapest in

July

Average price

$587
From Madison Truax Field to Simpson Bay Princess Juliana
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Highest demand for flights based on searches. 28% potential increase in price ($320 potential increase over avg. RT price).
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Cheapest flight prices on average. 9% potential price decrease ($70 potential savings vs. average RT price).
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Average for round-trip flights in July 2025
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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 July 30, 2025.

This Delta deal was found by Cheapflights users on 7/29. 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.
Fri 9/125:40 amMSN - SXM
1 stop7h 10mDelta
Fri 9/193:20 pmSXM - MSN
1 stop8h 39mDelta
Deal found 7/29$612
This American Airlines deal was found by Cheapflights users on 7/29. 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 12/114:20 pmMSN - SXM
2 stops21h 20mAmerican Airlines
Tue 12/163:35 pmSXM - MSN
2 stops20h 43mAmerican Airlines
Deal found 7/29$617
This Mytrip deal was found by Cheapflights users on 7/29. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/112:34 pmMSN - SXM
2 stops23h 26mMultiple Airlines
Tue 12/165:00 pmSXM - MSN
3 stops26h 28mMultiple Airlines
Deal found 7/29$1,318

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 July 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

Fri 9/12

5:40 am-1:50 pm

1 stop7h 10m

Simpson Bay Princess Juliana

Fri 9/19

3:20 pm-10:59 pm

1 stop8h 39m

$612

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Thu 12/11

4:20 pm-3:40 pm

2 stops21h 20m

Simpson Bay Princess Juliana

Tue 12/16

3:35 pm-10:18 am

2 stops20h 43m

$617

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Thu 12/11

2:34 pm-4:00 pm

2 stops23h 26m

Simpson Bay Princess Juliana

Tue 12/16

5:00 pm-5:28 pm

3 stops26h 28m

$1,318

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/29

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, September is the cheapest month in which you can book a flight from Madison to Simpson Bay (average of $459). Flying from Madison to Simpson Bay in March is currently the most expensive (average of $655). 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 July 30, 2025.

It’s typically best to fly out from Madison to Simpson Bay at noon. Doing so could potentially save you 42% on the flight price compared to flying in the afternoon, 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 July 30, 2025.
See what other customers who have flown with Delta and American Airlines 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
8.0
Very good
7,980 reviews

Entertainment

7.9

Boarding

8.2

Overall

8.0

Food

7.3

Comfort

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,980 reviews
Delta
8.0
Very good
7,980 reviews

Entertainment

7.9

Boarding

8.2

Overall

8.0

Food

7.3

Comfort

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,980 reviews

Entertainment

7.9

Boarding

8.2

Overall

8.0

Food

7.3

Comfort

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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.

  • What are the cheapest airlines flying from Madison to Simpson Bay round-trip?

    According to our current data, Delta ($612), and American Airlines ($617) offers the cheapest pricing from Madison to Simpson Bay. You may be able to fly from Madison to Simpson Bay for 22% less than the average price by searching for these airlines.

  • 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, September is the cheapest month in which you can book a flight from Madison to Simpson Bay (average of $459). Flying from Madison to Simpson Bay in March is currently the most expensive (average of $655). 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

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Top 2 airlines flying from Madison to Simpson Bay

Discover the top 2 airlines 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 July 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$587Average$645FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$647Average$784FlexibilityNo cancel feeOn-time71%

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