MSN - SXM

$617 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 7/30. 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
1 adult, Economy

KAYAK searches 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
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Cheap Flights 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 for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Madison to Simpson Bay

Wed, Jul 30 - Wed, Aug 6
American Airlines Logo
6:33 pm - 1:49 pmMSN-SXM
18h 16m2 stops
American Airlines Logo
3:25 pm - 9:18 amSXM-MSN
18h 53m2 stops
$617American Airlines
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Sun, Sep 28 - Sat, Oct 4
Delta Logo
5:45 am - 1:50 pmMSN-SXM
7h 05m1 stop
Delta Logo
3:15 pm - 10:34 pmSXM-MSN
8h 19m1 stop
$630Delta
Find Deal
Sun, Sep 28 - Sat, Oct 4
American Airlines Logo
12:47 pm - 1:19 pmMSN-SXM
23h 32m2 stops
American Airlines Logo
2:35 pm - 9:59 amSXM-MSN
20h 24m2 stops
$635American Airlines
Find Deal
Tue, Jul 1 - Thu, Jul 10
American Airlines Logo
4:21 pm - 1:34 pmMSN-SXM
20h 13m2 stops
American Airlines Logo
4:25 pm - 1:07 pmSXM-MSN
21h 42m2 stops
$727American Airlines
Find Deal
Tue, Jul 1 - Thu, Jul 10
American Airlines Logo
1:27 pm - 1:34 pmMSN-SXM
23h 07m2 stops
American Airlines Logo
2:50 pm - 12:29 pmSXM-MSN
22h 39m2 stops
$749American Airlines
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Tue, Jul 1 - Thu, Jul 10
American Airlines Logo
4:21 pm - 1:34 pmMSN-SXM
20h 13m2 stops
American Airlines Logo
2:15 pm - 11:50 pmSXM-MSN
10h 35m1 stop
$901American Airlines
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Tue, Jul 1 - Thu, Jul 10
American Airlines Logo
4:21 pm - 3:05 pmMSN-SXM
21h 44m2 stops
American Airlines Logo
2:15 pm - 11:50 pmSXM-MSN
10h 35m1 stop
$946American Airlines
Find Deal
Wed, Jul 30 - Wed, Aug 6
American Airlines Logo
12:24 pm - 1:25 pmMSN-SXM
24h 01m1 stop
American Airlines Logo
3:25 pm - 11:03 pmSXM-MSN
8h 38m1 stop
$1,040American Airlines
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Tue, Jul 1 - Thu, Jul 10
Delta Logo
5:45 am - 2:00 pmMSN-SXM
7h 15m1 stop
Delta Logo
3:21 pm - 10:34 pmSXM-MSN
8h 13m1 stop
$1,216Delta
Find Deal
Fri, Nov 21 - Mon, Dec 1
American Airlines Logo
4:29 pm - 2:15 pmMSN-SXM
19h 46m2 stops
American Airlines Logo
5:00 pm - 9:53 amSXM-MSN
18h 53m2 stops
$1,329American Airlines
Find Deal
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KAYAK's insights & trends for Madison to Simpson Bay flights

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.

Which airlines provide the cheapest flights from Madison to Simpson Bay?

The cheapest round-trip price for the route for each airline clicked by KAYAK users in the last 72 hours.

In the past 3 days, the cheapest round-trip tickets from Madison to Simpson Bay were found on American Airlines ($617) and Delta ($630).

Good to know

Low seasonMay
High seasonJanuary
Cheapest flight$617
Best time to beat the crowds with an average 35% drop in price.
Most popular time to fly with an average 1% 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 $617 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, and SkyTeam 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 $652 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 $784 and an overall rating of 7.2.

  • 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.

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 7963 reviews
8.5Crew
7.9Comfort
8.2Boarding
7.3Food
7.9Entertainment
Airline reviews

The flight was scheduled for 2:30 PM. Early in the morning we got a text message saying the flight was delayed and rescheduled for 3:00 PM. We got to the airport with that in mind. Then we got a message during check-in at the flight was rescheduled again for 2:30 PM. We almost missed our flight. In fact, our bags Were told that they would not make it. At the end, everything worked out. But it is very stressful.

4.0 OkayKoonj, Jun 2025MSP - AUS
Read more Delta reviews

The flight was scheduled for 2:30 PM. Early in the morning we got a text message saying the flight was delayed and rescheduled for 3:00 PM. We got to the airport with that in mind. Then we got a message during check-in at the flight was rescheduled again for 2:30 PM. We almost missed our flight. In fact, our bags Were told that they would not make it. At the end, everything worked out. But it is very stressful.

Overall, aside from the baggage issue, it was as good as one expects.

Most aspects were good however if they assign boarding zones they ought to enforce them or why bother? My luggage from SAN-JFK-MAD was lost in NY so I without my main bag for two days upon arrival in Spain. They were helpful in tracking it and eventually delivered it to my hotel. The flub was because of a delay upon arrival in NYC. I had booked 2 1/2 hours between flights but we had to hold on the taxiway for an hour after landing while waiting for a clear gate which likely caused the baggage error.

I want to single out flight attendant Mitch who was in the Premium Economy section. When my wife’s hearing aide dropped through the cushion under the seat he was able to locate it and return it to her. Food was a different matter. Dinner was fine. Breakfast was another matter. They had a yogurt dish that the ran out of and the alternative was not very good according to those we talked to.

Excellent check-in. Crew was good. Excellent communication from flight deck.

Great overall. There was a bit of turbulence so they could only serve water because too much turbulence for the carts. Was glad they prioritized safety though

Excellent flight, the planes were newer, they did a nice job with boarding, great service overall.

Flight was delayed long enough that I was misding my connecting flight. The agents could not get me on a comparable flight, nor could they get me s Main Cabin seat I had paid for, nor could they get me on a comparable connecting flight. The gate agent would not issue meal vouchers, even though I was delayed over six hours! I had to spend over an hour and 15 minutes with customer service on the phone to See if they could get me on a better flight and get a meal voucher. Customer service was not helpful enough in trying to find alternate flights and it Ended up taking me 24 hours for a 12 hour trip!! Delta does not provide upgrades NOR will they even give you a pass for a few hours to their lounge. They claim that they do not issue daily passes to their lounge anymore. I call BS since this would be no extra cost to them to provide excellent customer service and give you a few hours to relax in comfort when you’re sitting in a crowded airport and your flight has been screwed up for that many hours.

Great service. Flight was delayed while we sat on the runway for a couple of hours. Weather related. Staff made is very bearable. The steward servicing the first class cabin was exceptional. Thank you! 💗

5 hours of delay that could've been much shorter if Delta had taken the 1 hour delay they imposed on the flight before boarding to run any of the plane checks required for flight to find the hydraulic issue that required nearly 3 hours to fix. $24 of meal credit buys a sandwich and a soft drink. Poor communication within the terminal about what gate we'd be re-boarding from and when we'd be re-boarding.

The chair cushions may need an upgrade. I have been noticing they are so worn out, thin so you’d sit in a dip 😄. Other than that, all was an enjoyable trip. Thanks AA!

Food was terrible, all served at once, poor quality . Wine and bread offered only once.

I’m impressed that we were on time in Sacramento after having a late departure in Newark and our made it. The staff was friendly and warm.

Cramped seats. FAA should make airlines have more legroom, for even short people complain

5.5 hour delay with no explanation on why, along with no proactive effort to reaccomodate me.

It was one of my worst flight ever. First they were changing the gate for at least 4 times, changing from gate D7 to D12 to D44. Considering the size of the Miami Airport, we are talking about long distance and the train at the airport was not working. Then the flight was delayed around one hour. Then finally we boarded into the plane and when everybody was seated, there was an announcement that there is an issue with one of the tire of the plane, so we all had to get out of the plane with our belongings, to replace the tire. So we had around 2.5-hour delay

Most miserable flight ever. We waited almost 2 hours on the runway because the flight was oversold. American offered $1200 credit. Then there was some nonsense about weight distribution. Ridiculous. No food for 8 plus hours on the flight. I will be writing a letter.

Honestly, I haven’t flown American in years, probably due to the pandemic and my being unable to travel for certain periods in the last two years, but it was a good experience to dig out or obtain a new American Airlines account after many years of traveling for business with American in the past.

The plane was probably full boarding was easy. We were able to check our carry-on luggage for free. It was a return flight through Philly to LA. Never saw a stewardess do a demonstration of emergency Procedures. I think my flight was pretty full

Plane, flight, crew, captain were all great. The first flight had a Chipotle box lunch...delicious.

Everything you need to know for your flight from Madison to Simpson Bay

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