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Port of Spain

$1,178+ 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 1/24. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — POS
Jan 14 — Jan 211
Wed 1/14
Wed 1/21
1 adult, Economy
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Cheap flight deals from Madison to Port of Spain

Best flights from Madison to Port of Spain
Discover carefully curated flight deals from Madison to Port of Spain that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated December 15, 2025.

This Air Canada deal was found by Cheapflights users on 12/12. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/2412:32 pmMSN - POS
2 stops34h 48mAir Canada
Tue 1/272:20 amPOS - MSN
2 stops17h 27mAir Canada
Deal found 12/12$1,178

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 December 15, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$1,178
(Air Canada)
Provider with most accurate pricing for Madison Truax Field-Port of Spain Piarco Intl flight deals.
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Provider most trusted by Cheapflights users for Madison Truax Field-Port of Spain Piarco Intl flights.
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From Madison Truax Field to Port of Spain Piarco Intl
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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 December 15, 2025.
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

Sat 1/24

12:32 pm-1:20 am

2 stops34h 48m

Port of Spain Piarco Intl

Tue 1/27

2:20 am-5:47 pm

2 stops17h 27m

$1,178

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/12

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 December.
ProviderPrice AccuracyTrust Score*
AranGrantPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice 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 eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Madison-Port of Spain flight deals on Cheapflights vs. eDreams >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 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 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 December 15, 2025.
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
11,051 reviews

Overall

7.2

Boarding

7.5

Food

6.5

Entertainment

6.9

Crew

8.0

Comfort

7.2

Reviews

1 / 20
10.0
Excellent

Jeremy,Dec 2025

OKC - CLT

Was an okay flight. Had extra seat empty beside me so was able to stretch a bit
American Airlines
7.2
Good
11,051 reviews
American Airlines
7.2
Good
11,051 reviews

Overall

7.2

Boarding

7.5

Food

6.5

Entertainment

6.9

Crew

8.0

Comfort

7.2

Reviews

1 / 20
10.0
Excellent

Jeremy,Dec 2025

OKC - CLT

Was an okay flight. Had extra seat empty beside me so was able to stretch a bit

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?

    Air Canada can get you from Madison to Port of Spain in just under 34h 48m. Your travel time can differ by up to . Airlines will cover a distance of 2804 mi.

  • 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 December 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$602Average$1,066FlexibilityNo cancel feeOn-time71%

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