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$620+ Cheap flights from Simpson Bay (SXM) to Madison (MSN)

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 5/7. Fares are subject to change and may not be available on all flights or dates of travel.
SXM — MSN
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
1 adult, Economy
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Cheap 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 January 29, 2026.

This American Airlines deal was found by Cheapflights users on 1/27. 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.
Thu 5/72:24 pm
SXM
-
MSN
1 stop10h 31m
American Airlines
Sun 5/108:25 pm
MSN
-
SXM
2 stops15h 51m
American Airlines
Deal found 1/27$620
This Delta deal was found by Cheapflights users on 1/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/73:20 pm
SXM
-
MSN
2 stops18h 26m
Delta
Mon 5/115:45 am
MSN
-
SXM
1 stop7h 14m
Delta
Deal found 1/27$705
This American Airlines deal was found by Cheapflights users on 1/27. 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.
Thu 5/72:24 pm
SXM
-
MSN
1 stop10h 31m
American Airlines
Mon 5/115:08 pm
MSN
-
SXM
1 stop19h 13m
American Airlines
Deal found 1/27$748

Find 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 January 29, 2026.

Round-trip from

$620
(American Airlines)
From Simpson Bay Princess Juliana to Madison Truax Field
Search Deals

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 January 29, 2026.
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

Thu 5/7

2:24 pm-11:55 pm

1 stop10h 31m

Madison Truax Field

Sun 5/10

8:25 pm-1:16 pm

2 stops15h 51m

$620

Simpson BayMadison

SXM - MSN

SXMMSN

Simpson Bay Princess Juliana

Thu 5/7

3:20 pm-8:46 am

2 stops18h 26m

Madison Truax Field

Mon 5/11

5:45 am-1:59 pm

1 stop7h 14m

$705

Simpson BayMadison

SXM - MSN

SXMMSN

Simpson Bay Princess Juliana

Thu 5/7

2:24 pm-11:55 pm

1 stop10h 31m

Madison Truax Field

Mon 5/11

5:08 pm-1:21 pm

1 stop19h 13m

$748

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/28

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 10h 31m. The distance from Simpson Bay to Madison is about 2311 mi.

  • 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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