$406 Cheap Flights from Port of Spain (POS) to Madison (MSN)

View $406 flight on Tue, Sep 2, 2025Opens in a new window

Popular airlines from Piarco Intl. Airport (POS) to Dane County Regional Airport (MSN)

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Cheap Flights from Port of Spain to Madison (POS-MSN)

Prices were available within the past 7 days and start at $406 for one-way flights and $617 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

United
Wed, Aug 20 - Thu, Sep 4
POS
Trinidad
MSN
Madison
$617 Roundtrip, found 6 days ago
$617
Roundtrip
found 6 days ago
Select United flight, departing Wed, Aug 20 from Trinidad to Madison, returning Thu, Sep 4, priced at $617 found 6 days ago
United
Wed, Nov 26 - Thu, Dec 4
POS
Trinidad
MSN
Madison
$618 Roundtrip, found 2 days ago
$618
Roundtrip
found 2 days ago
Select United flight, departing Wed, Nov 26 from Trinidad to Madison, returning Thu, Dec 4, priced at $618 found 2 days ago
United
Wed, Aug 20 - Fri, Sep 5
POS
Trinidad
MSN
Madison
$629 Roundtrip, found 6 days ago
$629
Roundtrip
found 6 days ago
Select United flight, departing Wed, Aug 20 from Trinidad to Madison, returning Fri, Sep 5, priced at $629 found 6 days ago
United
Wed, Nov 26 - Fri, Dec 5
POS
Trinidad
MSN
Madison
$631 Roundtrip, found 2 days ago
$631
Roundtrip
found 2 days ago
Select United flight, departing Wed, Nov 26 from Trinidad to Madison, returning Fri, Dec 5, priced at $631 found 2 days ago
American Airlines
Fri, Nov 28 - Sun, Dec 7
POS
Trinidad
MSN
Madison
$636 Roundtrip, found 2 days ago
$636
Roundtrip
found 2 days ago
Select American Airlines flight, departing Fri, Nov 28 from Trinidad to Madison, returning Sun, Dec 7, priced at $636 found 2 days ago
United
Mon, Aug 18 - Wed, Aug 20
POS
Trinidad
MSN
Madison
$641 Roundtrip, found 6 days ago
$641
Roundtrip
found 6 days ago
Select United flight, departing Mon, Aug 18 from Trinidad to Madison, returning Wed, Aug 20, priced at $641 found 6 days ago
American Airlines
Fri, Nov 28 - Sun, Dec 7
POS
Trinidad
MSN
Madison
$645 Roundtrip, found 2 days ago
$645
Roundtrip
found 2 days ago
Select American Airlines flight, departing Fri, Nov 28 from Trinidad to Madison, returning Sun, Dec 7, priced at $645 found 2 days ago
United
Tue, Aug 19 - Tue, Aug 26
POS
Trinidad
MSN
Madison
$647 Roundtrip, found 6 days ago
$647
Roundtrip
found 6 days ago
Select United flight, departing Tue, Aug 19 from Trinidad to Madison, returning Tue, Aug 26, priced at $647 found 6 days ago
United
Tue, Aug 19 - Wed, Aug 20
POS
Trinidad
MSN
Madison
$647 Roundtrip, found 6 days ago
$647
Roundtrip
found 6 days ago
Select United flight, departing Tue, Aug 19 from Trinidad to Madison, returning Wed, Aug 20, priced at $647 found 6 days ago
American Airlines
Fri, Nov 28 - Sun, Dec 7
POS
Trinidad
MSN
Madison
$687 Roundtrip, found 2 days ago
$687
Roundtrip
found 2 days ago
Select American Airlines flight, departing Fri, Nov 28 from Trinidad to Madison, returning Sun, Dec 7, priced at $687 found 2 days ago
Flights from Port of Spain (POS) to Madison (MSN)
Origin airport
Piarco Intl.
Destination airport
Dane County Regional
Roundtrip price
$616
Distance
2806 mi

Port of Spain to Madison Flights

The cheapest times to fly from Port of Spain to Madison

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Port of Spain to Madison are during the month of August. You can find some of the cheapest flights from Port of Spain to Madison with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Port of Spain to Madison

Sunday is one of the best days to book for cheap flights from Port of Spain to Madison: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Port of Spain to Madison

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Port of Spain to Madison in 2025. You can also book with separate airlines for your outbound and return journeys, from $406 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Port of Spain to Madison flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Port of Spain to Madison airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Frequently asked questions

How much does a flight from Piarco Intl. Airport (POS) to Dane County Regional Airport (MSN) cost?
Discover the latest flight deals from POS to MSN by entering your preferred travel dates and searching on Expedia. Easily compare prices by departure date if you have flexibility with your schedule and use handy filters to explore prices for your preferred journey. As a member of One Key™, our free loyalty program, you can use Price Tracking to watch fares and receive notifications if prices go up or down.
What is the cheapest month to fly from POS to MSN?
The cheapest flights from POS to MSN are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
What is the cheapest airline that flies from POS to MSN?
Use the filter tool on Expedia to compare airlines and find the cheapest carrier that'll take you from POS to MSN. Sort your results by "Price (lowest to highest)" to snap up a great deal.
How many flights per day from Piarco Intl. Airport (POS) to Dane County Regional Airport (MSN)?
Direct flights from Piarco Intl. Airport (POS) to Dane County Regional Airport (MSN) aren't available daily, so you'll have to take a flight with a layover. Explore your options with Expedia's filters. Enter your travel details and pick either "1 Stop" or "2+ Stops."
What day of the week has the most flights from POS to MSN?
You'll typically find Tuesday the quietest day for flights, while Fridays tend to be the busiest.* However this can change from season to season and during peak travel times or public holidays.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Piarco Intl. Airport (POS) to Dane County Regional Airport (MSN)?
To reach Dane County Regional Airport (MSN) without delays, choose a flight that leaves Piarco Intl. Airport (POS) before 3 PM. The likelihood of cancellations is 22% higher, on average, for departures after this time.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
Is it cheaper to buy a plane ticket from Piarco Intl. Airport (POS) to Dane County Regional Airport (MSN) last-minute?
Last-minute fares from POS to MSN are usually more expensive. For the best rates, start searching for flights as early as possible. That being said, if you can play around with your travel dates, it's possible to land a cheap fare right before your trip.
Is it cheaper to book a POS to MSN flight and hotel package?
You'll typically save money by securing a POS to MSN flight and hotel package compared to booking separately. In fact, travelers could save hundreds of dollars by bundling with Expedia. And it's simple to manage everything in one place. Once you've chosen your preferred accommodations and flights, consider adding extras such as tours, car rentals and activities.
Can I cancel or change the date of my flight from Piarco Intl. Airport (POS) to Dane County Regional Airport (MSN)?
If you booked your POS to MSN flight in the last 24 hours, you may be able to cancel or modify it without fees. Depending on the airline and the ticket type you purchased, additional charges may apply for changes after that time. Airline policies and contact information can be found in your itinerary or confirmation email. Or, visit our Customer Service portal if you'd like more information.

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*Available to One Key members.