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

According to our current data, American Airlines ($600), Delta ($621), and United Airlines ($682) offers the cheapest pricing from Madison to Simpson Bay. You may be able to fly from Madison to Simpson Bay for 29% less than the average price by searching for these airlines.

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.

What is the cheapest day to fly from Madison to Simpson Bay?

Travelers seeking maximum savings on their Madison to Simpson Bay flight should consider departing on Wednesday mornings when fares are most often at their lowest. Friday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

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

Travelers have found that booking a Tuesday departure is the best way to save up to 45% on the cost of booking your flights compared to booking on days of the week where this route is of high demand.

What is the cheapest month to fly from Madison to Simpson Bay?

May is one of the best times of the year to fly to Simpson Bay from Madison. Prices for May average $847 per person but you can even find prices for as low as $504. The most expensive prices can be found in the month of February. Opting for a May flight can save you 66% on your journey compared to booking in February

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.

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.

$600+ Flights from Madison to Simpson Bay

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1. Tell us where you want to go

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Cheap flight deals from Madison to Simpson Bay

Most accurate provider	FlightHub 3 stars
Most trusted provider	FlightHub 3 stars
Round-trip from	$600 (American 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

Search Deals

Highest demand for flights based on searches. 22% potential increase in price ($242 potential increase over avg. RT price).

Search Deals

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 3, 2025.

Mon 6/25:21 pmMSN - SXM

2 stops18h 54mAmerican Airlines

Fri 6/62:20 pmSXM - MSN

1 stop10h 39mAmerican Airlines

Deal found 4/2

$600

Tue 6/35:30 amMSN - SXM

1 stop7h 24mDelta

Wed 6/113:25 pmSXM - MSN

1 stop8h 39mDelta

Deal found 4/2

$621

Tue 6/312:55 pmMSN - SXM

2 stops22h 34mUnited Airlines

Wed 6/113:55 pmSXM - MSN

2 stops19h 16mUnited Airlines

Deal found 4/2

$682

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 April 3, 2025.

Mon 6/25:21 pmMSN - SXM

2 stops18h 54mAmerican Airlines

Fri 6/62:20 pmSXM - MSN

1 stop10h 39mAmerican Airlines

Deal found 4/2

$600

Tue 6/35:30 amMSN - SXM

1 stop7h 24mDelta

Wed 6/113:25 pmSXM - MSN

1 stop8h 39mDelta

Deal found 4/2

$621

Tue 6/33:55 pmMSN - SXM

2 stops19h 34mUnited Airlines

Mon 6/91:35 pmSXM - MSN

2 stops21h 36mUnited Airlines

Deal found 4/2

$682

Last-minute flights from Madison to Simpson Bay
Discover last-minute flight deals from Madison to Simpson Bay. Data last updated April 3, 2025 and is based on user searches.

Fri 5/25:00 amMSN - SXM

2 stops9h 24mAmerican Airlines

Fri 5/93:24 pmSXM - MSN

2 stops17h 37mAmerican Airlines

Deal found 4/2

$976

Fri 5/3012:55 pmMSN - SXM

2 stops22h 34mUnited Airlines

Wed 6/41:35 pmSXM - MSN

2 stops21h 36mUnited Airlines

Deal found 4/2

$683

Sat 5/315:30 amMSN - SXM

1 stop7h 24mDelta

Thu 6/53:19 pmSXM - MSN

1 stop8h 42mDelta

Deal found 4/2

$622

Cheapflights Fare Finder

Use the filters below to find and compare flights from Madison to Simpson Bay that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Mon 6/2

5:21 pm-1:15 pm

2 stops18h 54m

Simpson Bay Princess Juliana

Fri 6/6

2:20 pm-11:59 pm

1 stop10h 39m

$600

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Tue 6/3

5:30 am-1:54 pm

1 stop7h 24m

Simpson Bay Princess Juliana

Wed 6/11

3:25 pm-11:04 pm

1 stop8h 39m

$621

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Tue 6/3

3:55 pm-12:29 pm

2 stops19h 34m

Simpson Bay Princess Juliana

Mon 6/9

1:35 pm-10:11 am

2 stops21h 36m

$682

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/2

Compare providers for flights from Madison to Simpson Bay

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.

Provider	Price Accuracy	Trust Score*
Expedia	Price Accuracy1 star	Trust Score*3 stars
FlightHub	Price Accuracy3 stars	Trust Score*3 stars
eDreams	Price Accuracy3 stars	Trust 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 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 time of day to fly from MSN to SXM?

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

Delta

8.0

Very good

7,897 reviews

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

7,897 reviews

Delta

8.0

Very good

7,897 reviews

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

8,619 reviews

Delta

8.0

Very good

7,897 reviews

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

7,897 reviews

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

What are the cheapest airlines flying from Madison to Simpson Bay round-trip?
According to our current data, American Airlines ($600), Delta ($621), and United Airlines ($682) offers the cheapest pricing from Madison to Simpson Bay. You may be able to fly from Madison to Simpson Bay for 29% 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

Airline	Cheapest	Average	Flexibility	On-time
Delta	Cheapest$559	Average$940	FlexibilityNo cancel fee	On-timeN/A
American Airlines	Cheapest$601	Average$741	FlexibilityNo cancel fee	On-time71%

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$600+ 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 6/2. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Madison to Simpson Bay with Cheapflights

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

Cheap flight deals from Madison to Simpson Bay

Most accurate provider

Most trusted provider

Round-trip from

Popular in

Cheapest in

Average price

Find flight deals from Madison to Simpson Bay

Cheapest flights from Madison to Simpson BayExplore 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 3, 2025.

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 3, 2025.

Cheapflights Fare Finder

Use the filters below to find and compare flights from Madison to Simpson Bay that are best for you.

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.

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.

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 3, 2025.

Reviews of airlines servicing Simpson Bay

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?

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

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

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

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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Madison to Simpson Bay

See prices for flight routes from nearby airports that may be better suited for you.

Top 2 airlines flying from Madison to Simpson Bay

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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 3, 2025.