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Trinidad and Tobago

$764+ 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 10/20. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — POS
Mar 22 — Mar 291
Sun 3/22
Sun 3/29
1 adult, Economy
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Cheap 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 February 20, 2026.

This United Airlines deal was found by Cheapflights users on 2/19. 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 10/205:00 am
MSN
-
POS
2 stops17h 23m
United Airlines
Fri 10/2312:30 am
POS
-
MSN
2 stops21h 24m
United Airlines
Deal found 2/19$764
This United Airlines deal was found by Cheapflights users on 2/19. 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.
Sun 2/2210:49 am
MSN
-
POS
2 stops11h 34m
United Airlines
Fri 2/272:20 am
POS
-
MSN
2 stops16h 24m
United Airlines
Deal found 2/19$964
This United Airlines deal was found by Cheapflights users on 2/19. 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 2/208:15 am
MSN
-
POS
2 stops14h 50m
United Airlines
Fri 2/271:30 am
POS
-
MSN
2 stops15h 27m
United Airlines
Deal found 2/19$1,069
This United Airlines deal was found by Cheapflights users on 2/19. 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.
Mon 2/238:15 am
MSN
-
POS
2 stops14h 50m
United Airlines
Fri 2/271:30 am
POS
-
MSN
2 stops14h 37m
United Airlines
Deal found 2/19$1,074
This Kiwi.com deal was found by Cheapflights users on 2/19. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/216:36 pm
MSN
-
POS
1 stop24h 39m
Multiple Airlines
Fri 2/273:40 am
POS
-
MSN
2 stops16h 16m
Multiple Airlines
Deal found 2/19$1,075
This American Airlines deal was found by Cheapflights users on 2/19. 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.
Sun 2/228:24 pm
MSN
-
POS
3 stops16h 42m
American Airlines
Sat 2/284:06 pm
POS
-
MSN
2 stops20h 30m
American Airlines
Deal found 2/19$2,625

Find 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 February 20, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars
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.
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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 February 20, 2026.
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
11,321 reviews

Boarding

7.5

Entertainment

6.9

Comfort

7.2

Food

6.4

Overall

7.2

Crew

8.0

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
11,321 reviews
American Airlines
7.2
Good
11,321 reviews

Boarding

7.5

Entertainment

6.9

Comfort

7.2

Food

6.4

Overall

7.2

Crew

8.0

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 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.

  • 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.

See more FAQs

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Alternative routes for Madison to Trinidad and Tobago

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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 February 20, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$653Average$1,098FlexibilityNo cancel feeOn-time71%

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