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Trinidad and Tobago

$563+ 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 12/3. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — POS
Nov 19 — Nov 261
Wed 11/19
Wed 11/26
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 October 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$563
(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.
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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 October 20, 2025.

This United Airlines deal was found by Cheapflights users on 10/19. 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.
Wed 12/36:30 amMSN - POS
2 stops15h 53mUnited Airlines
Tue 12/91:30 amPOS - MSN
2 stops15h 24mUnited Airlines
Deal found 10/19$563
This Kiwi.com deal was found by Cheapflights users on 10/19. 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.
Wed 12/36:08 pmMSN - POS
2 stops47h 52mMultiple Airlines
Wed 12/108:30 amPOS - MSN
1 stop10h 58mMultiple Airlines
Deal found 10/19$917
This United Airlines deal was found by Cheapflights users on 10/17. 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 10/288:25 amMSN - POS
2 stops13h 58mUnited Airlines
Thu 10/3012:30 amPOS - MSN
2 stops19h 51mUnited Airlines
Deal found 10/17$943
This American Airlines deal was found by Cheapflights users on 10/18. 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.
Thu 12/185:01 pmMSN - POS
2 stops20h 45mAmerican Airlines
Sun 1/44:46 pmPOS - MSN
2 stops19h 22mAmerican Airlines
Deal found 10/18$1,245
This American Airlines deal was found by Cheapflights users on 10/19. 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.
Wed 12/310:36 amMSN - POS
2 stops11h 23mAmerican Airlines
Wed 12/107:10 amPOS - MSN
3 stops13h 07mAmerican Airlines
Deal found 10/19$2,754

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 October 20, 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

Wed 12/3

6:30 am-12:23 am

2 stops15h 53m

Port of Spain Piarco Intl

Tue 12/9

1:30 am-2:54 pm

2 stops15h 24m

$563

MadisonPort of Spain

MSN - POS

MSNPOS

Madison Truax Field

Wed 12/3

6:00 am-11:59 pm

2 stops15h 59m

Port of Spain Piarco Intl

Wed 12/10

7:10 am-9:56 pm

2 stops16h 46m

$563

MadisonPort of Spain

MSN - POS

MSNPOS

Madison Truax Field

Wed 12/3

6:08 pm-8:00 pm

2 stops47h 52m

Port of Spain Piarco Intl

Wed 12/10

8:30 am-5:28 pm

1 stop10h 58m

$917

MadisonPort of Spain

MSN - POS

MSNPOS

Madison Truax Field

Thu 12/18

5:01 pm-3:46 pm

2 stops20h 45m

Port of Spain Piarco Intl

Sun 1/4

4:46 pm-10:08 am

2 stops19h 22m

$1,245

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/19

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 October 20, 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
11,024 reviews

Food

6.4

Entertainment

6.9

Overall

7.2

Comfort

7.2

Boarding

7.5

Crew

8.0

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
11,024 reviews
American Airlines
7.2
Good
11,024 reviews

Food

6.4

Entertainment

6.9

Overall

7.2

Comfort

7.2

Boarding

7.5

Crew

8.0

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 15h 53m. 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.

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 October 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$602Average$1,066FlexibilityNo cancel feeOn-time71%

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