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MSN - SXM

$501 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 5/8. 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
Fri 5/24
Fri 5/31

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 45,119,101 times on KAYAK, and here is why:

Save 22% or moreCompare multiple travel sites with one search.

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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
6:11 pm - 1:23 pmMSN-SXM
18h 12m2 stops
2:12 pm - 10:23 pmSXM-MSN
9h 11m1 stop
$501American Airlines
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Wed, May 8 - Wed, May 15
1:27 pm - 1:33 pmMSN-SXM
23h 06m2 stops
2:10 pm - 10:09 pmSXM-MSN
8h 59m1 stop
$528American Airlines
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Thu, Jul 4 - Mon, Jul 15
7:13 am - 1:13 pmMSN-SXM
29h 00m1 stop
2:10 pm - 10:09 pmSXM-MSN
8h 59m1 stop
$531American Airlines
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Thu, Jul 4 - Mon, Jul 15
6:43 pm - 1:13 pmMSN-SXM
17h 30m2 stops
2:45 pm - 12:11 pmSXM-MSN
22h 26m2 stops
$539American Airlines
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Tue, Jul 23 - Tue, Jul 30
7:05 am - 1:13 pmMSN-SXM
29h 08m1 stop
4:15 pm - 12:11 pmSXM-MSN
20h 56m2 stops
$546American Airlines
Find Deal
Tue, Jul 23 - Tue, Jul 30
6:43 pm - 1:13 pmMSN-SXM
17h 30m2 stops
2:10 pm - 10:09 pmSXM-MSN
8h 59m1 stop
$561American Airlines
Find Deal
Tue, Jul 23 - Mon, Jul 29
4:20 pm - 1:33 pmMSN-SXM
20h 13m2 stops
2:10 pm - 12:11 pmSXM-MSN
23h 01m2 stops
$563American Airlines
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Tue, Jul 23 - Mon, Jul 29
5:55 am - 1:49 pmMSN-SXM
6h 54m1 stop
3:19 pm - 10:33 pmSXM-MSN
8h 14m1 stop
$680Delta
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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

Good to know

High season

March

Cheapest flight

$501
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 $501 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 $696 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 $1,237 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 11004 reviews
7.9comfort
7.5food
8.2boarding
8.0entertainment
8.6crew
Airline reviews

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.

6.0 GoodDan, Apr 2024LGA - DEN
Read more about Delta reviews

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!

This flight was ridiculous. I had to have a connecting flight from New York to orlando Florida??? The flight left late and because it was a short flight there was no first class amenities. I had one alcohol drink. The flight crew was fine, but it sure did not feel like first class. Delta to me dropped the ball by giving me a connecting flight. By the time we got to Raleigh we would have missed the next flight. Lucky for me the flight never came so now I was stuck waiting for a later flight that came in late also.

Our flight was delayed in Atlanta. The staff could have gave us an explanation for the delay and how long it would be.

I liked the ease of checking in, luggage check in, wheel chair assistance, boarding and flight.

On my way home I had a layover. The flight from ATL to CLT was amended 5x while I was waiting. I could have driven home sooner. Overall from Dallas, Tx to Charlotte, NC I started my trip at 4:30pm, I didn’t get home until past midnight. I know things happen, but 5x to make me run back and forth in an airport from different terminals is excessive. I also upgraded to comfort + , I didn’t feel it was worth it. There was no benefit

On my way home I had a layover. The flight from ATL to CLT was amended 5x while I was waiting. I could have driven home sooner. Overall from Dallas, Tx to Charlotte, NC I started my trip at 4:30pm, I didn’t get home until past midnight. I know things happen, but 5x to make me run back and forth in an airport from different terminals is excessive.

They did a fine job. Can't wait to use Delta in the future.

There was a loud squeaky sound the whole time we were flying.

Had a broken tray in business class. Crew just shrugged it off.

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.

Entertainment was okay not because anything was wrong but it is a short flight so having no wifi is annoying but understandable. Crew was outstanding as usual

It was spectacular. I had basic Economy and was given so much space and their seats lean back so far. Staff was superb, food was superb, everything was superb, Finnair is Fantastic.

Those seats were way too narrow. I had the middle seat, one person was a very skinny person and we still couldn’t avoid touching each other anytime one of us moved. The other person was larger and we were basically sitting in each others lap the entire flight. There was zero entertainment. The flight was long enough to justify tvs, but no. Gotta sit there in your infant seat and twiddle your thumbs.

The Flight attendant had an attitude and didn't allow anyone any time to prepare for landing despite being absent throughout the entire trip

Flight boarded without pilots. Sat on plane for 3 hrs. after over an hour late boarding. Plane never took off. Had to deplane near midnight. Line for rebooking was 3 hours + long. I had to leave.

The flight was great but board was a nightmare. The gate was changed 4 times during the layover period

The experience was great and much better than the flight going out. of course I was in first class but the service was excellent

Cold air blew constantly on my legs almost making me numb.

Madison - Simpson Bay Flights

Departure:

Madison (MSN)United States

Destination:

Simpson Bay (SXM)St. Maarten

Return flight deals:

Simpson Bay - Madison

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