HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Port of Spain

$683+ 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 8/16. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — POS
Jun 28 — Jul 51
Sat 6/28
Sat 7/5
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Madison to Port of Spain with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 June 23, 2025.

Round-trip from

$683
(United Airlines)
From Madison Truax Field to Port of Spain Piarco Intl
Search Deals

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 June 23, 2025.

This United Airlines deal was found by Cheapflights users on 6/23. 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.
Sat 8/166:45 pmMSN - POS
2 stops27h 38mUnited Airlines
Thu 8/2112:30 amPOS - MSN
2 stops22h 56mUnited Airlines
Deal found 6/23$683
This American Airlines deal was found by Cheapflights users on 6/21. 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.
Sat 8/165:49 pmMSN - POS
2 stops19h 36mAmerican Airlines
Thu 8/213:35 pmPOS - MSN
2 stops18h 43mAmerican Airlines
Deal found 6/21$703

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 June 23, 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 8/16

6:45 pm-11:23 pm

2 stops27h 38m

Port of Spain Piarco Intl

Thu 8/21

12:30 am-10:26 pm

2 stops22h 56m

$683

MadisonPort of Spain

MSN - POS

MSNPOS

Madison Truax Field

Sat 8/16

5:49 pm-2:25 pm

2 stops19h 36m

Port of Spain Piarco Intl

Thu 8/21

3:35 pm-9:18 am

2 stops18h 43m

$703

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/23

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.

Cheapflights Insights

Everything you need to know about your flight from Madison to Port of Spain

Rainfall in Port of Spain by month

Plan your trip to Port of Spain by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Port of Spain ranges from 1.2 - 9.8 inches per month. June is typically the wettest month, when rainfall can reach 9.8 in. March is typically the driest time to visit Port of Spain when rainfall is around 1.2 in.

Temperature in Port of Spain by month

Plan your trip to Port of Spain by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Port of Spain, use this chart to help with planning. For those seeking warmer temperatures, April is the ideal time of year to visit, when temperatures reach an average of 80.6 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 77.0 F).

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 June 23, 2025.
United Airlines
7.4
Good
8,831 reviews

Entertainment

7.0

Boarding

7.7

Crew

8.1

Comfort

7.3

Food

6.6

Overall

7.4

Reviews

1 / 20
4.0
Okay

Thomas,Mar 2025

SFO - TPE

When I asked for an extra snack, I got an unhappy look from the stewardess. Geez, does one extra snack really affect the bottom line??
United Airlines
7.4
Good
8,831 reviews
United Airlines
7.4
Good
8,831 reviews

Entertainment

7.0

Boarding

7.7

Crew

8.1

Comfort

7.3

Food

6.6

Overall

7.4

Reviews

1 / 20
4.0
Okay

Thomas,Mar 2025

SFO - TPE

When I asked for an extra snack, I got an unhappy look from the stewardess. Geez, does one extra snack really affect the bottom line??
American Airlines
7.2
Good
10,000 reviews
United Airlines
7.4
Good
8,831 reviews

Entertainment

7.0

Boarding

7.7

Crew

8.1

Comfort

7.3

Food

6.6

Overall

7.4

Reviews

1 / 20
4.0
Okay

Thomas,Mar 2025

SFO - TPE

When I asked for an extra snack, I got an unhappy look from the stewardess. Geez, does one extra snack really affect the bottom line??

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.

  • 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.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Madison to Port of Spain

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Port of Spain flights
Minneapolis to Port of Spain flights
O'Hare Intl to Scarborough flights

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.