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MSN - SXM

Find cheap flights from Madison to Simpson Bay from $503

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 9/21. 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
Sat 4/27
Sat 5/4

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 46,342,885 times on KAYAK, and here is why:

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Cheap flight deals from Madison to Simpson Bay

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.
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4:28 pm - 1:22 pmMSN-SXM
19h 54m2 stops
4:00 pm - 10:00 amSXM-MSN
19h 00m2 stops
$503American Airlines
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Sat, Sep 21 - Sat, Oct 12
5:55 am - 1:49 pmMSN-SXM
6h 54m1 stop
3:19 pm - 10:33 pmSXM-MSN
8h 14m1 stop
$505Delta
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Sun, Sep 15 - Wed, Sep 18
5:55 am - 1:49 pmMSN-SXM
6h 54m1 stop
3:19 pm - 4:33 pmSXM-MSN
26h 14m2 stops
$509Delta
Find Deal
Sun, Sep 15 - Wed, Sep 18
5:25 pm - 3:05 pmMSN-SXM
20h 40m2 stops
12:35 pm - 10:23 pmSXM-MSN
10h 48m2 stops
$563American Airlines
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Wed, May 8 - Wed, May 15
6:01 am - 1:50 pmMSN-SXM
30h 49m2 stops
2:10 pm - 6:03 pmSXM-MSN
28h 53m2 stops
$603American Airlines
Find Deal
Tue, Jul 23 - Tue, Jul 30
4:28 pm - 1:22 pmMSN-SXM
19h 54m2 stops
2:45 pm - 9:24 pmSXM-MSN
7h 39m1 stop
$606American Airlines
Find Deal
Sat, Sep 21 - Sat, Oct 12
6:43 pm - 3:15 pmMSN-SXM
19h 32m2 stops
4:25 pm - 12:12 pmSXM-MSN
20h 47m2 stops
$608American Airlines
Find Deal
Mon, Jul 22 - Sat, Jul 27
5:55 am - 1:49 pmMSN-SXM
6h 54m1 stop
3:19 pm - 11:03 pmSXM-MSN
8h 44m1 stop
$809Delta
Find Deal
Tue, Jul 23 - Mon, Jul 29
6:32 am - 11:25 amMSN-SXM
27h 53m3 stops
3:55 pm - 10:13 amSXM-MSN
19h 18m2 stops
$2,259United Airlines
Find Deal
Mon, Jul 22 - Sat, Jul 27
6:32 am - 10:20 amMSN-SXM
50h 48m3 stops
12:50 pm - 10:27 pmSXM-MSN
10h 37m2 stops
$3,530United Airlines
Find Deal
Tue, Jul 23 - Tue, Jul 30

Flights from Madison to Simpson Bay - Travel Insights & Trends

Get data-powered insights and trends into flights from Madison to Simpson Bay to help you find the cheapest flights, the best time to fly and much more.

How long does a flight from Madison to Simpson Bay take?

Flying between Simpson Bay and Madison will take minimum 6h 54m and will require at least one stop.

Good to know

High season

March

Cheapest flight

$503
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 $503 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?

    oneworld, SkyTeam, 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 $686 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 $1,159 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

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 KAYAK reviews.
8.0
DeltaOverall score based on 11402 reviews
80entertainment
79comfort
82boarding
86crew
75food
81overall
Airline reviews

Carly the flight attendant was extremely helpful and very accommodating to passengers on the flight from what I noticed. Couldn't be more satisfied with the service and assistance from Delta's flight attendant, Thanks again Carly!!

Read more about Delta

Carly the flight attendant was extremely helpful and very accommodating to passengers on the flight from what I noticed. Couldn't be more satisfied with the service and assistance from Delta's flight attendant, Thanks again Carly!!

I didn’t not like that I could not select my seat and ended up with the worse seat.

I didn’t like that I could not select my seat and was assigned a seat when I checked in at LAX

Delta did an awful job w logistics at DTW. Missed connection. We were there an hour early. SUCKED

Inflight entertainment stopped working as we taxi to runway and never worked again until landing and taxi to gate. Grrrr

Had to run to make it only to have the flight delayed to wait for all the late connectors Second drink service skipped up

Boarding was a sh!t show. JFK BOARDING was awful. The agent called three sections at a time Clogging the area then yelling at people to not block the walk way. How are you going to call delta one , premium select and comfort plus at once and the yell at highest paying passengers. Need to do a lot better and the flight attendants in the galley need to understand that their voices travel. They were talking about others and everyone in the cabin heard them

Uncomfortable seats on 14 hour flight. Mediocre food. On time and great crew.

Please see my lengthy description on MSP to Atlanta survey. Tailbone is killing me from old hard seats. Seat would not recline and were not near exit row. Entertainment did not work properly and couldn’t use. No audio and touch screen failed. 3 plus hours of discomfort in narrower seats than previous flight not in comfort plus. Very dissatisfied and deserve comfort plus charges refunds, at the very least, for both my wife and I. The plane needs to be retired. Please feel free to contact me directly for further details.

MSP to Atlanta was much better than Atlanta to St. Kitts. Paid $180 each for myself and wife for Delta comfort from Atlanta to St. Kitts. Seats were more narrow and obviously old and worn out. Tailbone is killing me. Seat would not recline. Seats behind reclined and we were not an exit row or in front of an exit row. Entertainment did not work in that the movie jumped forward and back and there was no audio. The plug in the arm rest was loose. Flight attendant tried “resetting” the video for my seat but no good. She never checked back. Someone else near me had the same issue. Touch screen was unresponsive. No where near as comfortable as MSP to Atlanta flight. 3 plus hrs. flight time without the basic amenities and not even remotely close to comfortable but paid for Comfort plus. I will be very disappointed if I have the same on my return “Comfort Plus” flight St. Kitts to Atlanta. At the very least my wife and I should be refunded for round trip “Comfort Plus” charges. Please feel free to contact me directly for more details.

Plane was good but was delayed. probably not AA fault but caused a 1 hour delay. Seating was cramped.

Flight was good and arrived a little early. Very good.

Gossipy flight attendants talked the whole flight about bar hopping and dating.

Turbulence was bad and flight attendants gossiped about going to the bar and dating. Could have better awareness.

When we exited the plane our wheelchair wasn’t there. The Pilot and co pilot were so nice and helped us locate it. Great service.

Didn't like the 6 hour delay as it caused me to miss all of my connections. Still, I did get home safely 14 hours late but exhausted.

New ridiculous policy by american destroyed my allegiance to american. As a million miler with american, I expected it would be easy to get on an earlier flight when I got to airport earlier than expected, and save a five hour layover. WRONG. The online app would not let me switch flights, So I called, and was promised a call back in 90 minutes. HAH! The customer service desk at DCA said “we no longer have access to changing a flight on our screens. If the app couldn’t do it, I should send a letter to American, but there’s nothing else possible!”

We were delayed bc ground crew gave the flight crew the wrong paperwork. We taxiied to the runway then back to the gate to get the correct paperwork that no one bothered reviewing the first time we pushed back. Boarding was rude and stressful like it always is. Gate agents and flight attendants are all over 55 years of age, embittered by years of underpayment From AA leading to their passive agressive bitchiness for no reason.

Same basket of unhealthy prepackaged snacks (junk food) which was depleted by the time it got to my row!!

Lots of weather delays that were poorly communicated and managed. I get there are weather delays but they didn’t make it clear what was happening or comfortable on the plane

Madison - Simpson Bay Flights

Departure:

Madison (MSN)United States

Destination:

Simpson Bay (SXM)St. Maarten

Return flight deals:

Simpson Bay - Madison

Cabin classes: