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Port of Spain

$793+ 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 10/28. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — POS
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
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Cheap 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 September 15, 2025.

Round-trip from

$793
(American Airlines)
From Madison Truax Field to Port of Spain Piarco Intl
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Find 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 September 15, 2025.

This United Airlines deal was found by Cheapflights users on 9/14. 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 10/286:30 amMSN - POS
2 stops15h 53mUnited Airlines
Thu 10/3012:30 amPOS - MSN
2 stops18h 20mUnited Airlines
Deal found 9/14$793

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 September 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

Tue 10/28

6:00 am-9:20 pm

2 stops14h 20m

Port of Spain Piarco Intl

Fri 10/31

3:25 pm-10:35 am

2 stops20h 10m

$793

MadisonPort of Spain

MSN - POS

MSNPOS

Madison Truax Field

Tue 10/28

6:30 am-11:23 pm

2 stops15h 53m

Port of Spain Piarco Intl

Thu 10/30

12:30 am-7:21 pm

2 stops19h 51m

$793

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/12

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 September 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
10,000 reviews

Entertainment

6.9

Boarding

7.5

Crew

8.0

Food

6.4

Overall

7.2

Comfort

7.2

Reviews

1 / 20
2.0
Mediocre

Jeremy,Sep 2025

SAN - PHL

Terrible. Bad customer service and unacceptable delay on the tarmac
American Airlines
7.2
Good
10,000 reviews
American Airlines
7.2
Good
10,000 reviews

Entertainment

6.9

Boarding

7.5

Crew

8.0

Food

6.4

Overall

7.2

Comfort

7.2

Reviews

1 / 20
2.0
Mediocre

Jeremy,Sep 2025

SAN - PHL

Terrible. Bad customer service and unacceptable delay on the tarmac

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?

    American Airlines and United Airlines can get you from Madison to Port of Spain in just under 14h 20m. Your travel time can differ by up to 1h 33m. 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.

  • What is the cheapest month to book a flight from Madison to Port of Spain?

    Currently, October is the cheapest month in which you can book a flight from Madison to Port of Spain (average of $435). Flying from Madison to Port of Spain in December is currently the most expensive (average of $710). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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Alternative routes for Madison to Port of Spain

See prices for flight routes from nearby airports that may be better suited for you.
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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 September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$602Average$1,066FlexibilityNo cancel feeOn-time71%

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