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Trinidad and Tobago

$395+ Cheap flights from Wisconsin to Trinidad and Tobago

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 12/17. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — POS
Aug 16 — Aug 231
Sat 8/16
Sat 8/23
1 adult, Economy
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Cheap flight deals from Wisconsin to Trinidad and Tobago

Keep the following information in mind while searching for Wisconsin to Trinidad and Tobago flight deals. Data was last updated August 11, 2025.

Round-trip from

$505
(Kiwi.com)

One-way from

$395
(Air Canada)
From Wisconsin to Trinidad and Tobago
Search Deals
One-way flight from Wisconsin to Trinidad and Tobago
Search Deals

Find flight deals from Wisconsin to Trinidad and Tobago

Cheapest flights from Wisconsin to Trinidad and Tobago
Explore the most affordable flight options available from Wisconsin to Trinidad and Tobago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 11, 2025.

This Kiwi.com deal was found by Cheapflights users on 8/11. 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.
Mon 9/225:05 amORD - POS
1 stop13h 55mMultiple Airlines
Fri 9/269:10 amPOS - ORD
1 stop25h 08mMultiple Airlines
Deal found 8/11$505
This Kiwi.com deal was found by Cheapflights users on 8/11. 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.
Sun 9/2110:27 amORD - POS
1 stop16h 48mMultiple Airlines
Sun 9/286:25 pmPOS - ORD
1 stop15h 53mMultiple Airlines
Deal found 8/11$509
This Kiwi.com deal was found by Cheapflights users on 8/11. 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.
Sun 9/216:10 amORD - POS
2 stops18h 36mMultiple Airlines
Fri 9/2610:10 amPOS - ORD
1 stop25h 42mMultiple Airlines
Deal found 8/11$513
This Mytrip deal was found by Cheapflights users on 8/11. 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.
Mon 9/225:05 amORD - POS
1 stop13h 55mMultiple Airlines
Sat 9/279:10 amPOS - ORD
2 stops26h 32mMultiple Airlines
Deal found 8/11$527
This Kiwi.com deal was found by Cheapflights users on 8/11. 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.
Sun 9/216:10 amORD - POS
2 stops18h 36mMultiple Airlines
Sat 9/279:10 amPOS - ORD
1 stop25h 08mMultiple Airlines
Deal found 8/11$530
This Kiwi.com deal was found by Cheapflights users on 8/9. 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 10/227:11 pmORD - POS
1 stop23h 49mMultiple Airlines
Sun 10/266:25 pmPOS - ORD
1 stop15h 53mMultiple Airlines
Deal found 8/9$533
This Air Canada deal was found by Cheapflights users on 8/11. 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 9/2212:00 pmORD - POS
1 stop12h 20mAir Canada
Fri 9/262:25 amPOS - ORD
1 stop13h 39mAir Canada
Deal found 8/11$537
This Air Canada deal was found by Cheapflights users on 8/11. 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 12/18:15 pmORD - POS
1 stop26h 55mAir Canada
Sun 12/72:15 amPOS - ORD
2 stops18h 40mAir Canada
Deal found 8/11$542
This American Airlines deal was found by Cheapflights users on 8/10. 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 10/126:30 amMSP - POS
1 stop13h 50mAmerican Airlines
Thu 10/237:00 amPOS - MSP
1 stop16h 59mAmerican Airlines
Deal found 8/10$578
This American Airlines deal was found by Cheapflights users on 8/10. 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 9/75:39 pmMSP - POS
2 stops19h 37mAmerican Airlines
Thu 10/307:00 amPOS - MSP
2 stops17h 10mAmerican Airlines
Deal found 8/10$583
This American Airlines deal was found by Cheapflights users on 8/10. 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 12/46:19 pmMSP - POS
2 stops18h 40mAmerican Airlines
Sun 12/144:10 pmPOS - MSP
2 stops22h 41mAmerican Airlines
Deal found 8/10$588
This American Airlines deal was found by Cheapflights users on 8/10. 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 8/276:00 amMSP - POS
1 stop14h 36mAmerican Airlines
Wed 9/33:25 pmPOS - MSP
2 stops23h 44mAmerican Airlines
Deal found 8/10$623

Cheapflights Fare Finder

 
Customize your flight search to find flights from Wisconsin 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 August 11, 2025.
Use the filters below to find and compare flights from Wisconsin to Trinidad and Tobago that are best for you.

Fly from

Wisconsin

Fly to

Trinidad and Tobago

Route

Depart

Return

Price

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Mon 9/22

5:05 am-8:00 pm

1 stop13h 55m

Port of Spain Piarco Intl

Fri 9/26

9:10 am-9:18 am

1 stop25h 08m

$505

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sun 9/21

10:27 am-4:15 am

1 stop16h 48m

Port of Spain Piarco Intl

Sun 9/28

6:25 pm-9:18 am

1 stop15h 53m

$509

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sun 9/21

6:10 am-1:46 am

2 stops18h 36m

Port of Spain Piarco Intl

Fri 9/26

10:10 am-10:52 am

1 stop25h 42m

$513

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Mon 9/22

5:05 am-8:00 pm

1 stop13h 55m

Port of Spain Piarco Intl

Sat 9/27

9:10 am-10:42 am

2 stops26h 32m

$527

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sun 9/21

6:10 am-1:46 am

2 stops18h 36m

Port of Spain Piarco Intl

Sat 9/27

9:10 am-9:18 am

1 stop25h 08m

$530

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Wed 10/22

7:11 pm-8:00 pm

1 stop23h 49m

Port of Spain Piarco Intl

Sun 10/26

6:25 pm-9:18 am

1 stop15h 53m

$533

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Mon 9/22

12:00 pm-1:20 am

1 stop12h 20m

Port of Spain Piarco Intl

Fri 9/26

2:25 am-3:04 pm

1 stop13h 39m

$537

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Mon 12/1

8:15 pm-1:10 am

1 stop26h 55m

Port of Spain Piarco Intl

Sun 12/7

2:15 am-6:55 pm

2 stops18h 40m

$542

MinneapolisPort of Spain

MSP - POS

MSPPOS

Minneapolis St Paul

Sun 10/12

6:30 am-9:20 pm

1 stop13h 50m

Port of Spain Piarco Intl

Thu 10/23

7:00 am-10:59 pm

1 stop16h 59m

$578

MinneapolisPort of Spain

MSP - POS

MSPPOS

Minneapolis St Paul

Sun 9/7

5:39 pm-2:16 pm

2 stops19h 37m

Port of Spain Piarco Intl

Thu 10/30

7:00 am-11:10 pm

2 stops17h 10m

$583

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/11

Showing 1-10 of 20 results
1
2

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

Have a flexible travel schedule? Discover the best time to fly to Trinidad and Tobago 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 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 August 11, 2025.
See what other customers who have flown with Copa Airlines, United Airlines, and American Airlines from Wisconsin to Trinidad and Tobago have to say. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Copa Airlines
7.5
Good
1,506 reviews

Comfort

7.4

Boarding

7.8

Food

6.8

Crew

8.1

Overall

7.5

Entertainment

6.8

Reviews

1 / 20
4.0
Okay

Paul,Jun 2025

PTY - MIA

The boarding process was terrible. No one followed the group numbers. Everyone got up and stood in the tiles upon landing. People kept getting up during the meal and beverage service to go the bathrooms, the crew had to go back and forth in the isles, the service took forever.
Copa Airlines
7.5
Good
1,506 reviews
Copa Airlines
7.5
Good
1,506 reviews

Comfort

7.4

Boarding

7.8

Food

6.8

Crew

8.1

Overall

7.5

Entertainment

6.8

Reviews

1 / 20
4.0
Okay

Paul,Jun 2025

PTY - MIA

The boarding process was terrible. No one followed the group numbers. Everyone got up and stood in the tiles upon landing. People kept getting up during the meal and beverage service to go the bathrooms, the crew had to go back and forth in the isles, the service took forever.
United Airlines
7.4
Good
8,922 reviews
Copa Airlines
7.5
Good
1,506 reviews

Comfort

7.4

Boarding

7.8

Food

6.8

Crew

8.1

Overall

7.5

Entertainment

6.8

Reviews

1 / 20
4.0
Okay

Paul,Jun 2025

PTY - MIA

The boarding process was terrible. No one followed the group numbers. Everyone got up and stood in the tiles upon landing. People kept getting up during the meal and beverage service to go the bathrooms, the crew had to go back and forth in the isles, the service took forever.
American Airlines
7.2
Good
10,000 reviews
Copa Airlines
7.5
Good
1,506 reviews

Comfort

7.4

Boarding

7.8

Food

6.8

Crew

8.1

Overall

7.5

Entertainment

6.8

Reviews

1 / 20
4.0
Okay

Paul,Jun 2025

PTY - MIA

The boarding process was terrible. No one followed the group numbers. Everyone got up and stood in the tiles upon landing. People kept getting up during the meal and beverage service to go the bathrooms, the crew had to go back and forth in the isles, the service took forever.
Air Canada
7.1
Good
9,930 reviews
Copa Airlines
7.5
Good
1,506 reviews

Comfort

7.4

Boarding

7.8

Food

6.8

Crew

8.1

Overall

7.5

Entertainment

6.8

Reviews

1 / 20
4.0
Okay

Paul,Jun 2025

PTY - MIA

The boarding process was terrible. No one followed the group numbers. Everyone got up and stood in the tiles upon landing. People kept getting up during the meal and beverage service to go the bathrooms, the crew had to go back and forth in the isles, the service took forever.

Related info for your journey

Find useful and relevant information for your journey from Wisconsin 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.

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

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

  • How can I find direct flights from Wisconsin 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 Wisconsin to Trinidad and Tobago.

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

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

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

Discover the top airline that operate flights from Wisconsin 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 August 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$602Average$1,098FlexibilityNo cancel feeOn-time71%

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