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Port of Spain

$737+ Cheap flights from Madison (MSN) to Port of Spain (POS)

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 3/20. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — POS
Feb 26 — Mar 51
Thu 2/26
Thu 3/5
1 adult, Economy
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Cheap flight deals from Madison to Port of Spain

Cheapest flights from Madison to Port of Spain
Explore the most affordable flight options available from Madison to Port of Spain. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 27, 2026.

This United Airlines deal was found by Cheapflights users on 1/25. 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.
Fri 3/202:50 pm
MSN
-
POS
2 stops55h 33m
United Airlines
Sun 3/2912:30 am
POS
-
MSN
2 stops43h 23m
United Airlines
Deal found 1/25$737
This United Airlines deal was found by Cheapflights users on 1/25. 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.
Tue 10/206:45 am
MSN
-
POS
2 stops15h 38m
United Airlines
Fri 10/2312:30 am
POS
-
MSN
2 stops15h 55m
United Airlines
Deal found 1/25$754
This American Airlines deal was found by Cheapflights users on 1/25. 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.
Fri 3/208:24 pm
MSN
-
POS
3 stops16h 46m
American Airlines
Mon 3/303:10 pm
POS
-
MSN
2 stops18h 58m
American Airlines
Deal found 1/25$2,559
This Expedia deal was found by Cheapflights users on 1/25. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/205:44 pm
MSN
-
POS
3 stops30h 41m
Multiple Airlines
Mon 3/306:00 am
POS
-
MSN
3 stops36h 15m
Multiple Airlines
Deal found 1/25$5,273

Find flight deals from Madison to Port of Spain

Discover tips and strategies to find the most affordable flight options for your journey from Madison (MSN) to Port of Spain (POS). 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 27, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$737
(United Airlines)
Provider with most accurate pricing for Madison Truax Field-Port of Spain Piarco Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Madison Truax Field-Port of Spain Piarco Intl flights.
Search Deals
From Madison Truax Field to Port of Spain Piarco Intl
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Madison to Port of Spain 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 27, 2026.
Use the filters below to find and compare flights from Madison to Port of Spain that are best for you.

Fly from

Madison

Fly to

Port of Spain

Route

Depart

Return

Price

MadisonPort of Spain

MSN - POS

MSNPOS

Madison Truax Field

Fri 3/20

2:50 pm-11:23 pm

2 stops55h 33m

Port of Spain Piarco Intl

Sun 3/29

12:30 am-6:53 pm

2 stops43h 23m

$737

MadisonPort of Spain

MSN - POS

MSNPOS

Madison Truax Field

Fri 3/20

8:24 pm-2:10 pm

3 stops16h 46m

Port of Spain Piarco Intl

Mon 3/30

3:10 pm-9:08 am

2 stops18h 58m

$2,559

MadisonPort of Spain

MSN - POS

MSNPOS

Madison Truax Field

Fri 3/20

5:44 pm-1:25 am

3 stops30h 41m

Port of Spain Piarco Intl

Mon 3/30

6:00 am-5:15 pm

3 stops36h 15m

$5,273

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/25

Compare providers for flights from Madison to Port of Spain

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 Madison to Port of Spain in January.
ProviderPrice AccuracyTrust Score*
AranGrantPrice Accuracy2 starsTrust Score*2 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars

*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 Madison-Port of Spain flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Madison-Port of Spain flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Madison-Port of Spain flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Madison-Port of Spain flights, Cheapflights users trust FlightHub the most. FlightHub 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 Madison-Port of Spain 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 Madison to Port of Spain

Have a flexible travel schedule? Discover the best time to fly to Port of Spain from Madison 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.

Reviews of airlines servicing Port of Spain

Get insights into the airlines that provide service to Port of Spain. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Port of Spain. Reviews last updated January 27, 2026.
Read reviews from past customers who have flown American Airlines from Madison to Port of Spain. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.2
Good
11,197 reviews

Food

6.4

Entertainment

6.9

Overall

7.2

Comfort

7.2

Crew

8.0

Boarding

7.5

Reviews

1 / 20
2.0
Mediocre

Susie,Jan 2026

CLT - TPA

This flight was delayed 3 or 4 times. We had boarded the plane, sat on plane for a good 30 minutes, then we had to board the aircraft, walk to a different gate, wait and then board another aircraft. We arrived in Tampa 4 hours later than the original booking. I feel there should have been some sort of compensation especially for the advantage members.
American Airlines
7.2
Good
11,197 reviews
American Airlines
7.2
Good
11,197 reviews

Food

6.4

Entertainment

6.9

Overall

7.2

Comfort

7.2

Crew

8.0

Boarding

7.5

Reviews

1 / 20
2.0
Mediocre

Susie,Jan 2026

CLT - TPA

This flight was delayed 3 or 4 times. We had boarded the plane, sat on plane for a good 30 minutes, then we had to board the aircraft, walk to a different gate, wait and then board another aircraft. We arrived in Tampa 4 hours later than the original booking. I feel there should have been some sort of compensation especially for the advantage members.

Related info for your journey

Find useful and relevant information for your journey from Madison to Port of Spain. 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 Madison to Port of Spain?

    United Airlines and American Airlines can get you from Madison to Port of Spain in just under 16h 46m. Your travel time can differ by up to 38h 47m. Airlines will cover a distance of 2804 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • Can I find deals for flights from Madison to Port of Spain that include hotel bookings?

    Yes. In addition to deals on Madison to Port of Spain flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Madison to Port of Spain?

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

  • Can I find deals for business class flights from Madison to Port of Spain?

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

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Alternative routes for Madison to Port of Spain

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Top airline flying from Madison to Port of Spain

Discover the top airline that operate flights from Madison to Port of Spain. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated January 27, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$653Average$1,098FlexibilityNo cancel feeOn-time71%

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