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Trinidad and Tobago

$793+ Cheap flights from Madison (MSN) to Trinidad and Tobago

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 16 — Oct 231
Thu 10/16
Thu 10/23
1 adult, Economy
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Cheap flight deals from Madison to Trinidad and Tobago

Keep the following information in mind while searching for Madison to Trinidad and Tobago flight deals. Data was last updated September 16, 2025.

Round-trip from

$793
(American Airlines)
From Madison Truax Field to Trinidad and Tobago
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Find flight deals from Madison to Trinidad and Tobago

Cheapest flights from Madison to Trinidad and Tobago
Explore the most affordable flight options available from Madison to Trinidad and Tobago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 16, 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 Trinidad and Tobago 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 16, 2025.
Use the filters below to find and compare flights from Madison to Trinidad and Tobago that are best for you.

Fly from

Madison

Fly to

Trinidad and Tobago

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-12:28 pm

2 stops22h 03m

$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-5:50 pm

2 stops18h 20m

$793

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/13

Best time to book a flight from Madison to Trinidad and Tobago

Have a flexible travel schedule? Discover the best time to fly to Trinidad and Tobago 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.

Cheapflights Insights

Everything you need to know about your flight from Madison to Trinidad and Tobago
No data available for this route at this time. Please check back soon.

Reviews of airlines servicing Trinidad and Tobago

Get insights into the airlines that provide service to Trinidad and Tobago. 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 Trinidad and Tobago. Reviews last updated September 16, 2025.
Read through reviews of airlines operating flights from Madison to Trinidad and Tobago, such as American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.2
Good
10,000 reviews

Overall

7.2

Crew

8.0

Boarding

7.5

Comfort

7.2

Food

6.4

Entertainment

6.9

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

Overall

7.2

Crew

8.0

Boarding

7.5

Comfort

7.2

Food

6.4

Entertainment

6.9

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 Trinidad and Tobago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Madison to Trinidad and Tobago?

    Madison Truax Field (MSN) is the airport you will fly out of if you book a flight from Madison to Trinidad and Tobago. It is only a 5.4 mi journey to Truax Field (MSN) from Madison’s city center.

  • How long is the flight from Madison to Trinidad and Tobago?

    Departing from Madison to Trinidad and Tobago will take you 14h 20m. There are 2804 mi between Madison and Trinidad and Tobago. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • Can I find deals for flights from Madison to Trinidad and Tobago that include hotel bookings?

    Yes. In addition to deals on Madison to Trinidad and Tobago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Madison to Trinidad and Tobago?

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

  • Can I find deals for business class flights from Madison to Trinidad and Tobago?

    Yes. Cheapflights offers flight deals from Madison to Trinidad and Tobago 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 Trinidad and Tobago?

    Currently, October is the cheapest month in which you can book a flight from Madison to Trinidad and Tobago (average of $435). Flying from Madison to Trinidad and Tobago 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.

See more FAQs

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Top airline flying from Madison to Trinidad and Tobago

Discover the top airline that operate flights from Madison to Trinidad and Tobago. 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 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$602Average$1,066FlexibilityNo cancel feeOn-time71%

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