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Port of Spain

$188+ Cheap flights from Wisconsin to Port of Spain (POS)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 1/14. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — POS
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
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Cheap flight deals from Wisconsin to Port of Spain

Keep the following information in mind while searching for Wisconsin to Port of Spain flight deals. Data was last updated September 15, 2025.

Round-trip from

$423
(Air Canada)

One-way from

$188
(Air Canada)
From Wisconsin to Port of Spain Piarco Intl
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One-way flight from Wisconsin to Port of Spain Piarco Intl
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Find flight deals from Wisconsin to Port of Spain

Cheapest flights from Wisconsin to Port of Spain
Explore the most affordable flight options available from Wisconsin to Port of Spain. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 15, 2025.

This Air Canada deal was found by Cheapflights users on 9/13. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/153:50 pmORD - POS
1 stop8h 30mAir Canada
Fri 9/262:25 amPOS - ORD
1 stop9h 28mAir Canada
Deal found 9/13$423
This Air Canada deal was found by Cheapflights users on 9/12. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/212:00 pmORD - POS
1 stop9h 10mAir Canada
Fri 11/282:15 amPOS - ORD
2 stops18h 40mAir Canada
Deal found 9/12$428
This Air Canada deal was found by Cheapflights users on 9/13. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/212:00 pmORD - POS
1 stop9h 10mAir Canada
Thu 11/272:15 amPOS - ORD
1 stop14h 55mAir Canada
Deal found 9/13$473
This Kiwi.com deal was found by Cheapflights users on 9/13. 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 10/227:43 pmORD - POS
2 stops29h 03mMultiple Airlines
Sun 10/266:25 pmPOS - ORD
1 stop15h 57mMultiple Airlines
Deal found 9/13$493
This Mytrip deal was found by Cheapflights users on 9/13. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/146:20 pmORD - POS
1 stop30h 00mMultiple Airlines
Sun 9/216:25 pmPOS - ORD
1 stop15h 53mMultiple Airlines
Deal found 9/13$499
This Copa 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/63:07 pmORD - POS
1 stop9h 39mCopa Airlines
Wed 10/82:40 pmPOS - ORD
1 stop10h 41mCopa Airlines
Deal found 9/14$532
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.
Thu 9/187:00 amORD - POS
1 stop15h 23mUnited Airlines
Wed 10/1512:30 amPOS - ORD
1 stop10h 40mUnited Airlines
Deal found 9/14$548
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/67:45 amORD - POS
2 stops12h 45mAmerican Airlines
Wed 10/83:25 pmPOS - ORD
1 stop9h 33mAmerican Airlines
Deal found 9/14$553
This Mytrip deal was found by Cheapflights users on 9/13. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/188:25 pmORD - POS
1 stop27h 55mMultiple Airlines
Thu 9/256:25 pmPOS - ORD
1 stop15h 53mMultiple Airlines
Deal found 9/13$554
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.
Fri 10/178:00 amMSP - POS
1 stop14h 23mUnited Airlines
Mon 10/2012:30 amPOS - MSP
2 stops14h 51mUnited Airlines
Deal found 9/14$583
This United Airlines deal was found by Cheapflights users on 9/13. 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 10/116:00 amMSP - POS
2 stops16h 23mUnited Airlines
Fri 10/1712:30 amPOS - MSP
1 stop12h 39mUnited Airlines
Deal found 9/13$598
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/171:52 pmMSP - POS
2 stops23h 33mAmerican Airlines
Tue 10/217:00 amPOS - MSP
1 stop16h 59mAmerican Airlines
Deal found 9/14$613

Cheapflights Fare Finder

 
Customize your flight search to find flights from Wisconsin 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 Wisconsin to Port of Spain that are best for you.

Fly from

Wisconsin

Fly to

Port of Spain

Route

Depart

Return

Price

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Fri 11/21

2:00 pm-1:10 am

1 stop9h 10m

Port of Spain Piarco Intl

Fri 11/28

2:15 am-3:10 pm

1 stop14h 55m

$423

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sat 11/22

8:15 pm-1:10 am

1 stop26h 55m

Port of Spain Piarco Intl

Fri 11/28

2:15 am-3:10 pm

1 stop14h 55m

$423

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Fri 3/6

7:15 am-1:10 am

2 stops15h 55m

Port of Spain Piarco Intl

Thu 3/12

1:15 am-8:05 am

2 stops31h 50m

$433

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Fri 1/2

2:00 pm-1:10 am

1 stop9h 10m

Port of Spain Piarco Intl

Fri 1/9

2:15 am-1:01 pm

1 stop12h 46m

$473

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Wed 10/22

7:43 pm-1:46 am

2 stops29h 03m

Port of Spain Piarco Intl

Sun 10/26

6:25 pm-9:22 am

1 stop15h 57m

$493

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Fri 11/21

7:15 am-1:10 am

2 stops15h 55m

Port of Spain Piarco Intl

Thu 11/27

2:15 am-1:01 pm

1 stop12h 46m

$523

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Fri 3/6

2:22 pm-1:46 am

1 stop9h 24m

Port of Spain Piarco Intl

Sat 3/14

3:46 am-1:31 pm

1 stop10h 45m

$526

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Mon 10/6

3:07 pm-1:46 am

1 stop9h 39m

Port of Spain Piarco Intl

Wed 10/8

2:40 pm-12:21 am

1 stop10h 41m

$532

MinneapolisPort of Spain

MSP - POS

MSPPOS

Minneapolis St Paul

Wed 1/7

6:30 am-3:05 pm

1 stop30h 35m

Port of Spain Piarco Intl

Thu 1/15

4:45 pm-12:35 am

1 stop9h 50m

$571

MinneapolisPort of Spain

MSP - POS

MSPPOS

Minneapolis St Paul

Fri 10/17

8:00 am-11:23 pm

1 stop14h 23m

Port of Spain Piarco Intl

Mon 10/20

12:30 am-2:21 pm

2 stops14h 51m

$583

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 21 results
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Best time to book a flight from Wisconsin to Port of Spain

Have a flexible travel schedule? Discover the best time to fly to Port of Spain from Wisconsin 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 Wisconsin to Port of Spain
No data available for this route at this time. Please check back soon.

Related info for your journey

Find useful and relevant information for your journey from Wisconsin 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.

  • What airport do you fly into for flights to Port of Spain from Wisconsin?

    Port of Spain Piarco Intl (POS), located 12.6 mi from the city center, is the airport you fly into when you book flights from Wisconsin to Port of Spain.

  • How long is the flight from Wisconsin to Port of Spain?

    There are many flights that can get you from Wisconsin to Port of Spain in 9h 10m. Fly via Air Canada, American Airlines, or United Airlines to get the fastest option. The distance from Wisconsin to Port of Spain is about 2697 mi. This flight may include one or multiple stops.

  • What are the most popular routes from Wisconsin to Port of Spain?

    When deciding which route to take from Wisconsin to Port of Spain consider Chicago O'Hare Intl - Port of Spain Piarco Intl, Minneapolis St Paul - Port of Spain Piarco Intl or Madison Truax Field - Port of Spain Piarco Intl as they are the most popular.

  • Can I find deals for flights from Wisconsin to Port of Spain that include hotel bookings?

    Yes. In addition to deals on Wisconsin to Port of Spain flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Wisconsin 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 Wisconsin to Port of Spain.

  • Can I find deals for business class flights from Wisconsin to Port of Spain?

    Yes. Cheapflights offers flight deals from Wisconsin 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 Wisconsin to Port of Spain?

    Currently, October is the cheapest month in which you can book a flight from Wisconsin to Port of Spain (average of $435). Flying from Wisconsin 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

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Alternative routes for Wisconsin 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 Wisconsin to Port of Spain

Discover the top airline that operate flights from Wisconsin 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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