MSN - SXM

$646 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 2/11. 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
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

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

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

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

Wed, Feb 11 - Wed, Feb 25
American Airlines Logo
11:43 am - 1:22 pmMSN-SXM
23h 39m1 stop
American Airlines Logo
4:15 pm - 10:29 amSXM-MSN
20h 14m2 stops
$646American Airlines
Find Deal
Sat, Jan 10 - Sat, Jan 17
American Airlines Logo
4:17 pm - 3:20 pmMSN-SXM
21h 03m2 stops
American Airlines Logo
5:42 pm - 10:27 amSXM-MSN
18h 45m2 stops
$660American Airlines
Find Deal
Sat, Jan 10 - Sat, Jan 17
American Airlines Logo
12:19 pm - 1:55 pmMSN-SXM
23h 36m1 stop
American Airlines Logo
5:20 pm - 10:29 amSXM-MSN
19h 09m2 stops
$670American Airlines
Find Deal
Sat, Jan 10 - Sat, Jan 17
American Airlines Logo
7:07 am - 1:55 pmMSN-SXM
28h 48m1 stop
American Airlines Logo
5:42 pm - 10:29 amSXM-MSN
18h 47m1 stop
$677American Airlines
Find Deal
Wed, Feb 11 - Wed, Feb 25
American Airlines Logo
11:43 am - 1:22 pmMSN-SXM
23h 39m1 stop
American Airlines Logo
3:25 pm - 9:26 pmSXM-MSN
8h 01m1 stop
$701American Airlines
Find Deal
Wed, Feb 11 - Wed, Feb 25
American Airlines Logo
3:49 pm - 2:05 pmMSN-SXM
20h 16m2 stops
American Airlines Logo
5:20 pm - 10:29 amSXM-MSN
19h 09m2 stops
$795American Airlines
Find Deal

Everything you should know

Cheapest round-trip
$646
American Airlines
Wed 2/11Wed 2/25
MSN - SXM • 1 stop
Cheapest one-way
Multiple Airlines
Tue 9/16
MSN - SXM • multi-stop
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Simpson Bay!
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.

How much is a round-trip flight from Madison to Simpson Bay?

Find deals

Good to know

Low seasonJuly
Cheapest flight$646
Best time to beat the crowds with an average 24% 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 $646 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 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 7954 reviews
8.2Boarding
8.5Crew
7.9Entertainment
7.3Food
7.9Comfort
Airline reviews

Perfect flight both ways. On time, courteous staff, plane comfortable and cool. Best domestic flights I’ve had in awhile.

10.0 ExcellentAnonymous, Sep 2025CLT - BOS
Read more Delta reviews

Perfect flight both ways. On time, courteous staff, plane comfortable and cool. Best domestic flights I’ve had in awhile.

The food was terrible especially for a 15 hour international flight. The crew was unpleasant as well.

Really low quality food especially for an international flight. The crew also was surprisingly unpleasant except couple of ladies. I know we were not in first class but that’s no reason to treat customers as less.

Flight delayed for two and half hours and then canceled altogether due to mechanical issues. No mechanic onsite to fix so had to send one from LAX.

Quick check in. Everything went smooth. I don't know what can be done about airline food.

Crew was good. The reservation got mixed up and they didn't have my TSA number. I am also a Silver Medallion and wasn't able to use Sky Priority.

Delta made it easy, comfortable and timely. The crew was fantastic.

This route with Delta always has delays or is cancelled. Aircrafts seem smaller and older. I fly Delta quite a bit - haven’t had issues with the international flights. But this route has always been the troublesome one

Nothing special. The crew never went out of their way for anything.

Three seats in first class were broken and while they were able to still acommodate us it was looking very touch and go and they had others they could not acommodate

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

Information on your arrival and departure airports

Madison (MSN)
Simpson Bay (SXM)

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.