How long is the flight from Madison to Simpson Bay?

Airlines like American Airlines fly from Madison to Simpson Bay in about 23h 39m. 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 23% less than the average price by searching for this airline.

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?

July is one of the best times of the year to fly to Simpson Bay from Madison. Prices for July average $765 per person but you can even find prices for as low as $587. The most expensive prices can be found in the month of February. Opting for a July flight can save you 84% on your journey compared to booking in February

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.

$646+ Cheap Flights from Madison to Simpson Bay

Q: How much does it cost to fly round-trip from Madison to Simpson Bay?

Airfare is above average for this route at the moment. Madison to Simpson Bay flights typically cost between $616 and $625 in February. The cheapest round-trip price found within the last 3 days was $646 on American Airlines (Feb 11-Feb 25).

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Cheap flight deals from Madison to Simpson Bay

Round-trip from	$646 (American Airlines)
Popular in	February
Cheapest in	July
Average price	$621

From Madison Truax Field to Simpson Bay Princess Juliana

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Highest demand for flights based on searches. 26% potential increase in price ($269 potential increase over avg. RT price).

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Cheapest flight prices on average. 10% potential price decrease ($72 potential savings vs. average RT price).

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Average for round-trip flights in September 2025

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Find 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 September 15, 2025.

Wed 2/1111:43 amMSN - SXM

1 stop23h 39mAmerican Airlines

Wed 2/254:15 pmSXM - MSN

2 stops20h 14mAmerican Airlines

Deal found 9/14

$646

Sat 1/104:17 pmMSN - SXM

2 stops21h 03mAmerican Airlines

Sat 1/175:42 pmSXM - MSN

2 stops18h 45mAmerican Airlines

Deal found 9/14

$660

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

Wed 2/11

11:43 am-1:22 pm

1 stop23h 39m

Simpson Bay Princess Juliana

Wed 2/25

4:15 pm-10:29 am

2 stops20h 14m

$646

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Sat 1/10

4:17 pm-3:20 pm

2 stops21h 03m

Simpson Bay Princess Juliana

Sat 1/17

5:42 pm-10:27 am

2 stops18h 45m

$660

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

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 $652). 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?

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.

How much does it cost to fly round-trip from Madison to Simpson Bay?

Reviews of airlines servicing Simpson Bay

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

7,954 reviews

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

7,954 reviews

Delta

8.0

Very good

7,954 reviews

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

7,954 reviews

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

How long is the flight from Madison to Simpson Bay?
Airlines like American Airlines fly from Madison to Simpson Bay in about 23h 39m. 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 23% 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, 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 $652). 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.

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Top 2 airlines flying from Madison to Simpson Bay

Airline	Cheapest	Average	Flexibility	On-time
Delta	Cheapest$587	Average$645	FlexibilityNo cancel fee	On-timeN/A
American Airlines	Cheapest$647	Average$784	FlexibilityNo cancel fee	On-time71%

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$646+ 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 2/11. 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

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Cheap flight deals from Madison to Simpson Bay

Round-trip from

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Cheapest in

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Find flight deals from Madison to Simpson Bay

Best flights from Madison to Simpson BayDiscover 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 September 15, 2025.

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 September 15, 2025.

Cheapflights Fare Finder

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

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 month to book a flight from Madison to Simpson Bay?

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

How much does it cost to fly round-trip from Madison to Simpson Bay?

Reviews of airlines servicing Simpson Bay

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.

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?

What is the cheapest airline to fly 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?

Traveling to a place near Simpson Bay?

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Alternative routes for Madison to Simpson Bay

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Top 2 airlines flying from Madison to Simpson Bay

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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 September 15, 2025.