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MSN - SXM

$475 Find cheap flights from Madison to Simpson Bay

This is the cheapest round-trip flight price found by a KAYAK user in the last 72 hours by searching for a flight from Madison to Simpson Bay departing on 9/15. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
0 bags
Wed 5/29
Wed 6/5

Search hundreds of travel sites at once for deals on flights to Simpson Bay

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Madison to Simpson Bay, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Madison to Simpson Bay, as well as popular online travel agencies
In the last 7 days travelers have searched 43,219,010 times on KAYAK, and here is why:

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Cheap flight deals from Madison to Simpson Bay (MSN-SXM)

Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Madison to Simpson Bay that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
5:55 am - 1:49 pmMSN-SXM
6h 54m1 stop
3:19 pm - 10:33 pmSXM-MSN
8h 14m1 stop
$475Delta
Find Deal
Sun, Sep 15 - Wed, Sep 18
4:11 pm - 1:49 pmMSN-SXM
20h 38m2 stops
3:19 pm - 10:33 pmSXM-MSN
8h 14m1 stop
$479Delta
Find Deal
Sun, Sep 15 - Wed, Sep 18
6:38 pm - 1:13 pmMSN-SXM
17h 35m2 stops
2:45 pm - 10:47 amSXM-MSN
21h 02m2 stops
$539American Airlines
Find Deal
Tue, Jul 23 - Tue, Jul 30
4:20 pm - 1:13 pmMSN-SXM
19h 53m2 stops
2:10 pm - 10:09 pmSXM-MSN
8h 59m1 stop
$561American Airlines
Find Deal
Tue, Jul 23 - Mon, Jul 29
6:38 pm - 1:13 pmMSN-SXM
17h 35m2 stops
2:10 pm - 12:11 pmSXM-MSN
23h 01m2 stops
$563American Airlines
Find Deal
Tue, Jul 23 - Mon, Jul 29
1:27 pm - 1:33 pmMSN-SXM
23h 06m2 stops
2:10 pm - 10:09 pmSXM-MSN
8h 59m1 stop
$588American Airlines
Find Deal
Thu, Jul 4 - Mon, Jul 15
5:55 am - 1:49 pmMSN-SXM
6h 54m1 stop
3:19 pm - 10:33 pmSXM-MSN
8h 14m1 stop
$680Delta
Find Deal
Sun, Sep 15 - Wed, Sep 18
5:55 am - 1:49 pmMSN-SXM
6h 54m1 stop
3:19 pm - 8:45 amSXM-MSN
18h 26m2 stops
$684Delta
Find Deal
Sun, Sep 15 - Wed, Sep 18
6:32 am - 11:25 amMSN-SXM
27h 53m3 stops
3:55 pm - 10:13 amSXM-MSN
19h 18m2 stops
$2,254United Airlines
Find Deal
Mon, Jul 22 - Sat, Jul 27
6:35 am - 12:10 pmMSN-SXM
28h 35m3 stops
12:50 pm - 8:54 pmSXM-MSN
33h 04m2 stops
$6,267United Airlines
Find Deal
Mon, Sep 30 - Tue, Oct 8

Good to know

High season

March

Cheapest flight

$475
Most popular time to fly with an average 11% increase in price.
Flight from Madison to Simpson Bay

When to book flights from Madison to Simpson Bay

Are your dates flexible? Find out the best times to travel from Madison to Simpson Bay based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking flights from Madison to Simpson Bay

  • What is the cheapest flight from Madison to Simpson Bay?

    In the last 3 days, the lowest price for a flight from Madison to Simpson Bay was $475 for a round-trip ticket.

  • Do I need a passport to fly between Madison and Simpson Bay?

    A passport is required to fly from Madison to Simpson Bay.

  • Which airports will I be using when flying from Madison to Simpson Bay?

    Madison airport is called Madison Truax Field and the only airport in Simpson Bay is Simpson Bay Princess Juliana.

  • Which aircraft models fly most regularly from Madison to Simpson Bay?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Madison to Simpson Bay?

    SkyTeam, oneworld, and Star Alliance are the airline alliances operating flights between Madison and Simpson Bay, with SkyTeam being the most commonly used for this route.

  • Which is the best airline for flights from Madison to Simpson Bay, Delta or American Airlines?

    The two airlines most popular with KAYAK users for flights from Madison to Simpson Bay are Delta and American Airlines. With an average price for the route of $694 and an overall rating of 8.0, Delta is the most popular choice. American Airlines is also a great choice for the route, with an average price of $1,233 and an overall rating of 7.3.

  • How does KAYAK find such low prices on flights from Madison to Simpson Bay?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Madison to Simpson Bay.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Madison to Simpson Bay?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Simpson Bay from Madison is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Madison to Simpson Bay?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Simpson Bay with an airline and back to Madison with another airline. Booking your flights between Madison and SXM can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Madison to Simpson Bay?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Simpson Bay from Madison up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top airlines flying from Madison to Simpson Bay

 
See real verified KAYAK customer reviews for airlines flying from Madison to Simpson Bay. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Madison to Simpson Bay? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
DeltaOverall score based on 10913 reviews
8.0entertainment
7.4food
8.2boarding
8.6crew
7.9comfort
Airline reviews

Big plane, long flight, absolutely no leg room and basically non existent air! I am 5”4’ and always travel Main Cabin, I was miserable on this plane and could barely move when we arrived in Cabo due to the cramped leg area!

8.0 ExcellentCynthia, Apr 2024ATL - SJD
Read more about Delta reviews

Big plane, long flight, absolutely no leg room and basically non existent air! I am 5”4’ and always travel Main Cabin, I was miserable on this plane and could barely move when we arrived in Cabo due to the cramped leg area!

From Atlanta to Cabo I would have hoped on a plane that size I would have been able to breathe and wiggle my feet a little! The leg room in that plane is non existent and I am only 5”4’. And the air vent either wasn’t working very well or just could not blow air from the ceiling to the seat area as I was suffocating through the entire flight! And please don’t say I would have been more comfortable in first class because I cannot afford those rates and have always travelled Main Cabin without issues !

The pilots were good. Disappointing when planes don't have electrical ports

I liked the piloting of the aircraft. Very disappointed about lack of electrical ports. Also, although a short flight. there was enough time to hand out snacks to comfort + seats as was done for first class.

I had a wonderful experience flying with delta. The gentleman taking care of us on our flight was so nice, accommodating, and attentive. He always was smiling and giving pins to the kids which made me smile. The flight was quick too and without turbulence. Thank you for the great flying experience.

Delta is one of the best airlines I have flown

Made the Atlanta to Pittsburgh trip many times, with Delta no issues

I always fly with Delta. My friends tell me their horror stories of flying with other airlines. I just smile and say, “You should fly Delta”

I'm a larger, athletic guy (6'2", 260lbs powerlifter) and I found the seats incredibly uncomfortable with minimal leg room, especially in a window seat. Now, I full understand that being smaller may change my view but even if I was 80lbs less, my legs would be the same size and I was sandwiched between my seat and the seat in front of me.

Horrible. This was not first class. This was a connecting flight whi h was late. My original flight never came. I hated the fact that delta gave me a connecting flight from New York to Orlando Florida. No meals and the television screens were not working. There wasn't even any power to charge your phones. This is NOT FIRST CLASS DELTA!!! Do better next time!

LATE LATE LATE!!! Plagued by late AA flights on this trip. Such a drag. This one was by far the worst.

WiFi connected but only let you go to the AA website, not even text messaging worked.

Too bad that first class seats do not recline significantly causing discomfort

I think the seats on some of their planes are uncomfortable. You can be ok on a short flight of two hours but no more than that. The delays, and also the refreshments on the plane were not enough.

Flight delayed over an over all day until it cancelled at 1:30am. Would not repeatedly delay that late. Offer hotel rooms and rebook early. Very difficult for families with small children

Not sure why JAL partnered with American Airlines because their service is no where near similar. Flight attendants were not friendly and didn’t smile. Food was horrible…

this is starting to seem like an american airlines standard. delayed flights and fake apologies… getting tired of it

Terrible boarding , Business class seats are sub standard. As usual crew will miss your food too

Just get Economy Plus for international flights, so worth it the extra room, bigger seats…

This flight is frequently delayed. The connections seemingly are more frequently delayed. I’ve missed connections as a result twice on the same route to charlotte then Charleston. Final destination arrival has been the next day, twice in a row. No pilots, no crew. Too many excuses. Unfortunately, my days with American are over.

Madison - Simpson Bay Flights

Departure:

Madison (MSN)United States

Destination:

Simpson Bay (SXM)St. Maarten

Return flight deals:

Simpson Bay - Madison

Cabin classes: