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$370+ Cheap flights from Simpson Bay (SXM) to Madison (MSN)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/16. Fares are subject to change and may not be available on all flights or dates of travel.
SXM — MSN
Nov 28 — Dec 51
Fri 11/28
Fri 12/5
1 adult, Economy
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Cheap flight deals from Simpson Bay to Madison

Discover tips and strategies to find the most affordable flight options for your journey from Simpson Bay (SXM) to Madison (MSN). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated October 29, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$642
(United Airlines)

One-way from

$370
(Delta)
Provider with most accurate pricing for Simpson Bay Princess Juliana-Madison Truax Field flight deals.
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Provider most trusted by Cheapflights users for Simpson Bay Princess Juliana-Madison Truax Field flights.
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From Simpson Bay Princess Juliana to Madison Truax Field
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One-way flight from Simpson Bay Princess Juliana to Madison Truax Field
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Find flight deals from Simpson Bay to Madison

Cheapest flights from Simpson Bay to Madison
Explore the most affordable flight options available from Simpson Bay to Madison. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 29, 2025.

This United Airlines deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/272:40 pmSXM - MSN
1 stop9h 50mUnited Airlines
Fri 1/210:45 amMSN - SXM
2 stops25h 05mUnited Airlines
Deal found 10/27$642
This American Airlines deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/273:28 pmSXM - MSN
2 stops20h 02mAmerican Airlines
Fri 1/28:10 pmMSN - SXM
2 stops17h 54mAmerican Airlines
Deal found 10/27$692

Cheapflights Fare Finder

 
Customize your flight search to find flights from Simpson Bay to Madison that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated October 29, 2025.
Use the filters below to find and compare flights from Simpson Bay to Madison that are best for you.

Fly from

Simpson Bay

Fly to

Madison

Route

Depart

Return

Price

Simpson BayMadison

SXM - MSN

SXMMSN

Simpson Bay Princess Juliana

Sat 12/27

2:40 pm-10:30 pm

1 stop9h 50m

Madison Truax Field

Fri 1/2

10:45 am-1:50 pm

2 stops25h 05m

$642

Simpson BayMadison

SXM - MSN

SXMMSN

Simpson Bay Princess Juliana

Sat 12/27

1:39 pm-11:53 pm

1 stop12h 14m

Madison Truax Field

Fri 1/2

8:10 pm-4:04 pm

2 stops17h 54m

$692

Simpson BayMadison

SXM - MSN

SXMMSN

Simpson Bay Princess Juliana

Thu 4/23

2:35 pm-9:18 pm

1 stop7h 43m

Madison Truax Field

Sun 4/26

7:15 am-2:10 pm

2 stops29h 55m

$702

Simpson BayMadison

SXM - MSN

SXMMSN

Simpson Bay Princess Juliana

Tue 12/16

3:53 pm-10:26 pm

1 stop8h 33m

$370

Simpson BayMadison

SXM - MSN

SXMMSN

Simpson Bay Princess Juliana

Wed 12/17

2:51 pm-11:40 pm

1 stop10h 49m

$375

Simpson BayMadison

SXM - MSN

SXMMSN

Simpson Bay Princess Juliana

Sat 2/7

4:28 pm-5:59 pm

3 stops51h 31m

$377

Simpson BayMadison

SXM - MSN

SXMMSN

Simpson Bay Princess Juliana

Tue 12/16

3:20 pm-10:31 am

2 stops21h 11m

$379

Simpson BayMadison

SXM - MSN

SXMMSN

Simpson Bay Princess Juliana

Sat 12/27

2:40 pm-10:30 pm

1 stop9h 50m

$400

Simpson BayMadison

SXM - MSN

SXMMSN

Simpson Bay Princess Juliana

Sat 2/7

2:03 pm-11:59 pm

1 stop11h 56m

$400

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/27

Compare providers for flights from Simpson Bay to Madison

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Simpson Bay to Madison in October.
ProviderPrice AccuracyTrust Score*
eDreamsPrice Accuracy3 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Simpson Bay-Madison flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Simpson Bay-Madison flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Simpson Bay-Madison flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Simpson Bay-Madison flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Simpson Bay-Madison flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Simpson Bay to Madison

Have a flexible travel schedule? Discover the best time to fly to Madison from Simpson Bay with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Related info for your journey

Find useful and relevant information for your journey from Simpson Bay to Madison. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Simpson Bay to Madison?

    Departing from Simpson Bay to Madison will take you 9h 50m. The distance from Simpson Bay to Madison is about 2311 mi. This flight may include one or multiple stops.

  • Can I find deals for flights from Simpson Bay to Madison that include hotel bookings?

    Yes. In addition to deals on Simpson Bay to Madison flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Simpson Bay to Madison?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Simpson Bay to Madison.

  • Can I find deals for business class flights from Simpson Bay to Madison?

    Yes. Cheapflights offers flight deals from Simpson Bay to Madison by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

Traveling to a place near Madison?

Book flights to Madison if you plan to visit one of these locations
Portage
Middleton
Baraboo
Fitchburg

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