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

According to our current data, American Airlines ($617), Delta ($706), and United Airlines ($1,283) offers the cheapest pricing from Madison to Simpson Bay. You may be able to fly from Madison to Simpson Bay for 19% 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 March is currently the most expensive (average of $657). 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 $768 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 83% 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.

$293+ Flights from Madison to Simpson Bay

Home Search by date Vacation packages Hotels Flight deals Car rental Travel tips & news

Find cheap flights from Madison to Simpson Bay with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Madison to Simpson Bay

Round-trip from	$617 (American Airlines)
One-way from	$293 (Delta)
Popular in	February
Cheapest in	May
Average price	$621

From Madison Truax Field to Simpson Bay Princess Juliana

Search Deals

One-way flight from Madison Truax Field to Simpson Bay Princess Juliana

Search Deals

Highest demand for flights based on searches. 30% potential increase in price ($343 potential increase over avg. RT price).

Search Deals

Cheapest flight prices on average. 9% potential price decrease ($65 potential savings vs. average RT price).

Search Deals

Average for round-trip flights in June 2025

Search Deals

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 June 12, 2025.

Sat 9/132:01 pmMSN - SXM

2 stops22h 18mAmerican Airlines

Sat 9/202:35 pmSXM - MSN

1 stop9h 35mAmerican Airlines

Deal found 6/11

$617

Sat 9/135:45 amMSN - SXM

1 stop7h 05mDelta

Sat 9/203:15 pmSXM - MSN

1 stop8h 19mDelta

Deal found 6/11

$706

Sat 11/225:33 pmMSN - SXM

1 stop20h 24mUnited Airlines

Sun 11/302:20 pmSXM - MSN

1 stop23h 24mUnited Airlines

Deal found 6/10

$1,283

Fri 11/2112:19 pmMSN - SXM

2 stops25h 56mAir Canada

Mon 12/15:15 pmSXM - MSN

2 stops25h 36mAir Canada

Deal found 6/12

$1,348

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 June 12, 2025.

Sat 9/132:01 pmMSN - SXM

2 stops22h 18mAmerican Airlines

Sat 9/202:35 pmSXM - MSN

1 stop9h 35mAmerican Airlines

Deal found 6/11

$617

Sat 9/135:45 amMSN - SXM

1 stop7h 05mDelta

Sat 9/203:15 pmSXM - MSN

1 stop8h 19mDelta

Deal found 6/11

$706

Sat 11/225:33 pmMSN - SXM

1 stop20h 24mUnited Airlines

Sun 11/302:20 pmSXM - MSN

1 stop23h 24mUnited Airlines

Deal found 6/10

$1,283

Fri 11/2112:19 pmMSN - SXM

2 stops25h 56mAir Canada

Mon 12/15:15 pmSXM - MSN

2 stops25h 36mAir Canada

Deal found 6/12

$1,348

Last-minute flights from Madison to Simpson Bay
Discover last-minute flight deals from Madison to Simpson Bay. Data last updated June 12, 2025 and is based on user searches.

Sat 6/145:33 pmMSN - SXM

2 stops20h 32mAmerican Airlines

Tue 6/172:20 pmSXM - MSN

1 stop10h 39mAmerican Airlines

Deal found 6/12

$1,030

One-way flights from Madison to Simpson Bay
Search for one-way flight options from Madison to Simpson Bay. Find affordable one-way fares based on user searches. Data last updated June 12, 2025.

Tue 7/155:40 amMSN - SXM

1 stop7h 16mDelta

Deal found 6/11

$293

Wed 7/94:11 pmMSN - SXM

2 stops20h 38mAmerican Airlines

Deal found 6/11

$318

Wed 7/96:25 pmMSN - SXM

3 stops42h 35mMultiple Airlines

Deal found 6/11

$385

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

Sat 9/13

2:01 pm-1:19 pm

2 stops22h 18m

Simpson Bay Princess Juliana

Sat 9/20

2:35 pm-11:10 pm

1 stop9h 35m

$617

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Sat 9/13

5:45 am-1:50 pm

1 stop7h 05m

Simpson Bay Princess Juliana

Sat 9/20

3:15 pm-10:34 pm

1 stop8h 19m

$706

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Sat 11/22

5:33 pm-3:57 pm

1 stop20h 24m

Simpson Bay Princess Juliana

Sun 11/30

2:20 pm-11:44 am

1 stop23h 24m

$1,283

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Fri 11/21

12:19 pm-4:15 pm

2 stops25h 56m

Simpson Bay Princess Juliana

Mon 12/1

5:15 pm-4:51 pm

2 stops25h 36m

$1,348

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Tue 7/15

5:40 am-1:56 pm

1 stop7h 16m

$293

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Wed 7/9

4:11 pm-1:49 pm

2 stops20h 38m

$318

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Wed 7/9

6:25 pm-2:00 pm

3 stops42h 35m

$385

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/11

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

7,950 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

7,950 reviews

Delta

8.0

Very good

7,950 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!

United Airlines

7.4

Good

8,790 reviews

Delta

8.0

Very good

7,950 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

7,950 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!

Air Canada

7.1

Good

9,531 reviews

Delta

8.0

Very good

7,950 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

What are the cheapest airlines flying from Madison to Simpson Bay round-trip?
According to our current data, American Airlines ($617), Delta ($706), and United Airlines ($1,283) offers the cheapest pricing from Madison to Simpson Bay. You may be able to fly from Madison to Simpson Bay for 19% 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 $657). 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

Browse thousands of different options on Cheapflights for your next trip

Alternative routes for Madison to Simpson Bay

O'Hare Intl to Simpson Bay flights

Minneapolis to Simpson Bay flights

Milwaukee to Simpson Bay flights

Appleton to Simpson Bay flights

Green Bay to Simpson Bay flights

Eau Claire to Simpson Bay flights

Other flights to Simpson Bay

Fort Lauderdale to Simpson Bay flights

Orlando to Simpson Bay flights

Miami to Simpson Bay flights

John F Kennedy Intl to Simpson Bay flights

Newark to Simpson Bay flights

Boston to Simpson Bay flights

Simpson Bay to Fort Lauderdale flights

Simpson Bay to Santo Domingo flights

Simpson Bay to San Juan Luis Munoz Marin Intl Airport flights

Simpson Bay to Gustavia flights

Simpson Bay to Panama City flights

Simpson Bay to Newark Airport flights

Simpson Bay to Basseterre flights

Simpson Bay to Santo Domingo flights

Simpson Bay to Toronto Pearson Intl Airport flights

Simpson Bay to Road Town flights

Simpson Bay to Roseau flights

Simpson Bay to Fort Lauderdale flights

Simpson Bay to St. John's, Saint John flights

Simpson Bay to Orlando Airport flights

Simpson Bay to Miami flights

Simpson Bay to Washington, D.C. Dulles Intl Airport flights

Simpson Bay to Newark Airport flights

Top 2 airlines flying from Madison to Simpson Bay

Airline	Cheapest	Average	Flexibility	On-time
American Airlines	Cheapest$504	Average$784	FlexibilityNo cancel fee	On-time71%
Delta	Cheapest$559	Average$652	FlexibilityNo cancel fee	On-timeN/A

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.

$293+ 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 7/15. 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

Round-trip from

One-way 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 June 12, 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 June 12, 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 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 June 12, 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

100% Free

Book with Flexibility

Travel Smart

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 June 12, 2025.