MSN - SXM

$506 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 2/7. 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, 0 bags

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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Everything you should know

Cheapest round-trip
$506
Typical prices: $1,113-$1,455
American Airlines
Sat 2/7Fri 2/13
MSN - SXM • 2 stops
Cheapest one-way
Multiple Airlines
Wed 12/17
MSN - SXM • multi-stop
Top airlines
Delta
Cheapest • from $524 (round-trip)
Delta
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
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We hope you love your trip to Simpson Bay!
Flight Deals
Booking Insights
Flight Deals

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

Sat, Feb 7 - Fri, Feb 13
American Airlines Logo
4:47 pm - 4:28 pm
MSN
-
SXM
21h 41m2 stops
American Airlines Logo
1:41 pm - 11:59 pm
SXM
-
MSN
12h 18m2 stops
$506American Airlines
Mon, Feb 2 - Mon, Feb 9
American Airlines Logo
4:30 pm - 2:31 pm
MSN
-
SXM
20h 01m2 stops
American Airlines Logo
4:24 pm - 10:55 am
SXM
-
MSN
20h 31m2 stops
$536American Airlines
Fri, Feb 6 - Wed, Feb 11
American Airlines Logo
11:29 am - 3:07 pm
MSN
-
SXM
25h 38m1 stop
American Airlines Logo
3:09 pm - 11:47 pm
SXM
-
MSN
10h 38m1 stop
$537American Airlines
Mon, Feb 2 - Mon, Feb 9
American Airlines Logo
4:30 pm - 1:45 pm
MSN
-
SXM
19h 15m1 stop
American Airlines Logo
4:24 pm - 11:41 pm
SXM
-
MSN
9h 17m1 stop
$541American Airlines
Mon, Feb 9 - Mon, Feb 16
American Airlines Logo
4:30 pm - 1:45 pm
MSN
-
SXM
19h 15m1 stop
American Airlines Logo
3:05 pm - 9:57 am
SXM
-
MSN
20h 52m2 stops
$545American Airlines
Wed, Jan 14 - Wed, Jan 21
American Airlines Logo
3:09 pm - 12:58 pm
MSN
-
SXM
19h 49m2 stops
American Airlines Logo
5:33 pm - 10:55 am
SXM
-
MSN
19h 22m2 stops
$574American Airlines
Wed, Jan 14 - Wed, Jan 21
American Airlines Logo
4:47 pm - 2:31 pm
MSN
-
SXM
19h 44m1 stop
American Airlines Logo
3:09 pm - 11:47 pm
SXM
-
MSN
10h 38m1 stop
$580American Airlines
Sat, Feb 7 - Fri, Feb 13
American Airlines Logo
6:00 am - 3:07 pm
MSN
-
SXM
7h 07m1 stop
American Airlines Logo
3:33 pm - 10:10 am
SXM
-
MSN
20h 37m1 stop
$582American Airlines
Tue, Mar 3 - Tue, Mar 10
American Airlines Logo
5:07 pm - 3:36 pm
MSN
-
SXM
20h 29m2 stops
American Airlines Logo
12:29 pm - 10:56 pm
SXM
-
MSN
11h 27m2 stops
$592American Airlines
Tue, Mar 3 - Tue, Mar 10
American Airlines Logo
4:45 pm - 3:36 pm
MSN
-
SXM
20h 51m1 stop
American Airlines Logo
3:01 pm - 10:56 pm
SXM
-
MSN
8h 55m1 stop
$598American Airlines
Booking Insights

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 Delta ($524) and American Airlines ($536).

Which airlines fly non-stop between Madison and Simpson Bay?

Airline and price data is aggregated from results in KAYAK’s search results from the last 2 weeks for round-trip flights from Madison to Simpson Bay.

There is just one airline that flies from Madison to Simpson Bay direct and that is Delta. The best round-trip deal found from Delta for the route is $587.

Good to know

Low seasonJuly
Cheapest flight$506
Best time to beat the crowds with an average 29% drop in price.
Most popular time to fly with an average 10% 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 $506 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 is the only airline alliance operating flights between Madison and Simpson Bay.

  • 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.

Reviews of the top airline 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.
7.9
DeltaOverall score based on 8008 reviews
8.5Crew
7.9Comfort
7.3Food
8.1Boarding
7.9Entertainment
Airline reviews

I noticed that the planes seem to be outdated. There was no entertainment per se. Also, the waiting area did not have any working electrical outlets

10.0 ExcellentMargaret, Dec 2025
BOS - PIT
Read more Delta reviews

I noticed that the planes seem to be outdated. There was no entertainment per se. Also, the waiting area did not have any working electrical outlets

None of the airplane features were available during the flight.

Original flight was cancelled and when i was rebooked by the airline, they couldn't seat me in the same type of seat as I had originally booked (went from window/aisle to middle/middle and one was a bulkhead seat, and other wasn't in the same class)

Lady Pilot was perfect in every way wheels up to wheels down communication, professionalism, excellent on time departure and on time arrival, excellent communication! Fantastic job with Superb attitude!!

The food is terrible. The staff is wonderful. Comfort is good.

Left on time, a bit delayed due to headwinds most of the trip.

I fly Delta all the time, have Platinum Medallion status. But this route seems to have major problems with delays and seems to never leave on time! Have only taken it twice in the last two weeks, and each time it had delays of more than 1 hour... very disappointed!!!!

Getting to the flight was arduous and lengthy. The flight itself was good but the food option wasn’t a good selection. I need to do a Kosher option on my return. Flight crew were nice

Good seats in Main cabin, excellent service and excellent landing

My flight was cancelled with no explanation after I had already cleared security. I was given 4 options to rebook, only one being non-stop like I had paid for. I grabbed it. It was 4 plus hours later and then took off even later. Biggest complaint is that I booked early and had an aisle seat. They gave me a "window" seat in front of the exit row, so the seat did not decline. I weigh all of 103 #s and it was tight for me! For what I paid, I feel I was kind of ripped off. I think they should have given me the empty comfort seat for the inconvenience. There was no apology nor any explanation as to why the flight was cancelled. My guess is it benefitted Delta in some way.

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

Information on your arrival and departure airports