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Simpson Bay

$617+ 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 6/6. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — SXM
Apr 29 — May 61
Tue 4/29
Tue 5/6
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 April 24, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$617
(United Airlines)

Popular in

February

Cheapest in

May

Average price

$784
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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Highest demand for flights based on searches. 22% potential increase in price ($242 potential increase over avg. RT price).
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Cheapest flight prices on average. 7% potential price decrease ($63 potential savings vs. average RT price).
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Average for round-trip flights in April 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 April 24, 2025.

This United Airlines deal was found by Cheapflights users on 4/22. 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 6/62:35 pmMSN - SXM
2 stops20h 54mUnited Airlines
Fri 6/131:35 pmSXM - MSN
2 stops21h 36mUnited Airlines
Deal found 4/22$617
This American Airlines deal was found by Cheapflights users on 4/22. 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 6/66:40 pmMSN - SXM
2 stops19h 25mAmerican Airlines
Fri 6/132:20 pmSXM - MSN
1 stop10h 39mAmerican Airlines
Deal found 4/22$657
This Delta deal was found by Cheapflights users on 4/22. 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.
Sat 6/215:40 amMSN - SXM
1 stop7h 20mDelta
Sat 6/283:25 pmSXM - MSN
1 stop8h 18mDelta
Deal found 4/22$879

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 April 24, 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 6/6

2:35 pm-12:29 pm

2 stops20h 54m

Simpson Bay Princess Juliana

Fri 6/13

1:35 pm-10:11 am

2 stops21h 36m

$617

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Fri 6/6

6:40 pm-3:05 pm

2 stops19h 25m

Simpson Bay Princess Juliana

Fri 6/13

2:20 pm-11:59 pm

1 stop10h 39m

$657

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Sat 6/21

5:40 am-2:00 pm

1 stop7h 20m

Simpson Bay Princess Juliana

Sat 6/28

3:25 pm-10:43 pm

1 stop8h 18m

$879

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/22

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 April.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*2 stars
eDreamsPrice 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 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 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 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 April 24, 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 April 24, 2025.
Delta
8.0
Very good
7,920 reviews

Entertainment

7.9

Comfort

7.9

Crew

8.5

Boarding

8.2

Food

7.3

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Delta
8.0
Very good
7,920 reviews
Delta
8.0
Very good
7,920 reviews

Entertainment

7.9

Comfort

7.9

Crew

8.5

Boarding

8.2

Food

7.3

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
United Airlines
7.4
Good
8,685 reviews
Delta
8.0
Very good
7,920 reviews

Entertainment

7.9

Comfort

7.9

Crew

8.5

Boarding

8.2

Food

7.3

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,920 reviews

Entertainment

7.9

Comfort

7.9

Crew

8.5

Boarding

8.2

Food

7.3

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

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, United Airlines ($617), American Airlines ($657), and Delta ($879) offers the cheapest pricing from Madison to Simpson Bay. You may be able to fly from Madison to Simpson Bay for 27% 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 July is currently the most expensive (average of $675). 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 April 24, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$559Average$945FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$601Average$741FlexibilityNo cancel feeOn-time71%

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