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$314+ Cheap flights from Trinidad and Tobago to Wisconsin

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 12/25. Fares are subject to change and may not be available on all flights or dates of travel.
POS — MKE
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
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Cheap flight deals from Trinidad and Tobago to Wisconsin

Keep the following information in mind while searching for Trinidad and Tobago to Wisconsin flight deals. Data was last updated September 15, 2025.

Round-trip from

$452
(Priceline)

One-way from

$314
(American Airlines)
From Trinidad and Tobago to Wisconsin
Search Deals
One-way flight from Trinidad and Tobago to Wisconsin
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Find flight deals from Trinidad and Tobago to Wisconsin

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

This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/281:15 amPOS - ORD
2 stops43h 45mAir Canada
Wed 11/58:15 pmORD - POS
1 stop26h 55mAir Canada
Deal found 9/14$452
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/292:27 pmPOS - ORD
2 stops19h 55mMultiple Airlines
Wed 11/55:59 pmORD - POS
1 stop24h 01mMultiple Airlines
Deal found 9/14$463
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.
Tue 10/283:51 amPOS - ORD
1 stop10h 50mCopa Airlines
Wed 11/56:56 amORD - POS
1 stop16h 52mCopa Airlines
Deal found 9/14$562
This United Airlines deal was found by Cheapflights users on 9/15. 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 11/41:30 amPOS - MKE
2 stops14h 28mUnited Airlines
Wed 11/128:00 amMKE - POS
1 stop14h 23mUnited Airlines
Deal found 9/15$612
This United Airlines deal was found by Cheapflights users on 9/15. 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 12/121:30 amPOS - MSP
1 stop13h 40mUnited Airlines
Sat 1/107:35 amMSP - POS
1 stop14h 48mUnited Airlines
Deal found 9/15$637
This United Airlines deal was found by Cheapflights users on 9/15. 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 11/71:30 amPOS - MKE
2 stops15h 37mUnited Airlines
Sat 11/155:00 amMKE - POS
2 stops17h 23mUnited Airlines
Deal found 9/15$637
This American Airlines deal was found by Cheapflights users on 9/15. 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 11/87:19 amPOS - MKE
2 stops17h 46mAmerican Airlines
Sat 11/155:00 amMKE - POS
2 stops16h 39mAmerican Airlines
Deal found 9/15$641
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/134:33 pmPOS - MSP
1 stop32h 16mAmerican Airlines
Sat 1/105:21 pmMSP - POS
2 stops19h 44mAmerican Airlines
Deal found 9/13$655
This United Airlines deal was found by Cheapflights users on 9/15. 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 12/221:30 amPOS - MSP
2 stops16h 18mUnited Airlines
Fri 1/26:45 pmMSP - POS
2 stops28h 20mUnited Airlines
Deal found 9/15$703
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.
Fri 10/312:30 amPOS - MKE
1 stop10h 36mUnited Airlines
Sat 10/1810:18 amMKE - POS
1 stop12h 05mUnited Airlines
Deal found 9/13$708
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 11/910:10 amPOS - MKE
2 stops26h 23mMultiple Airlines
Thu 11/1311:57 amMKE - POS
1 stop29h 33mMultiple Airlines
Deal found 9/15$713
This American Airlines deal was found by Cheapflights users on 9/15. 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 11/77:19 amPOS - MKE
2 stops17h 37mAmerican Airlines
Thu 11/133:36 pmMKE - POS
2 stops21h 54mAmerican Airlines
Deal found 9/15$727

Cheapflights Fare Finder

 
Customize your flight search to find flights from Trinidad and Tobago to Wisconsin 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 Trinidad and Tobago to Wisconsin that are best for you.

Fly from

Trinidad and Tobago

Fly to

Wisconsin

Route

Depart

Return

Price

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Tue 10/28

1:15 am-8:00 pm

2 stops43h 45m

Chicago O'Hare Intl

Wed 11/5

8:15 pm-1:10 am

1 stop26h 55m

$452

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Wed 10/29

2:27 pm-9:22 am

2 stops19h 55m

Chicago O'Hare Intl

Wed 11/5

5:59 pm-8:00 pm

1 stop24h 01m

$463

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Tue 10/28

3:51 am-1:41 pm

1 stop10h 50m

Chicago O'Hare Intl

Wed 11/5

6:56 am-1:48 am

1 stop16h 52m

$562

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Thu 2/26

1:30 am-11:09 am

1 stop11h 39m

Chicago O'Hare Intl

Tue 3/3

7:35 am-12:23 am

1 stop14h 48m

$574

Port of SpainMilwaukee

POS - MKE

POSMKE

Port of Spain Piarco Intl

Sun 11/9

1:30 am-5:17 pm

2 stops17h 47m

Milwaukee-Mitchell

Mon 11/17

8:00 am-12:23 am

1 stop14h 23m

$612

Port of SpainMilwaukee

POS - MKE

POSMKE

Port of Spain Piarco Intl

Tue 11/4

1:30 am-2:50 pm

1 stop15h 20m

Milwaukee-Mitchell

Sun 11/16

8:00 am-12:23 am

1 stop14h 23m

$612

Port of SpainMilwaukee

POS - MKE

POSMKE

Port of Spain Piarco Intl

Tue 11/4

1:30 am-2:50 pm

1 stop15h 20m

Milwaukee-Mitchell

Mon 11/17

8:00 am-12:23 am

1 stop14h 23m

$612

Port of SpainMilwaukee

POS - MKE

POSMKE

Port of Spain Piarco Intl

Thu 11/6

1:30 am-5:17 pm

2 stops17h 47m

Milwaukee-Mitchell

Sun 11/16

8:00 am-12:23 am

1 stop14h 23m

$612

Port of SpainMilwaukee

POS - MKE

POSMKE

Port of Spain Piarco Intl

Wed 11/5

1:30 am-4:32 pm

2 stops17h 02m

Milwaukee-Mitchell

Mon 11/17

6:05 am-12:23 am

2 stops16h 18m

$612

Port of SpainMilwaukee

POS - MKE

POSMKE

Port of Spain Piarco Intl

Mon 11/10

1:30 am-1:58 pm

2 stops14h 28m

Milwaukee-Mitchell

Mon 11/17

8:00 am-12:23 am

1 stop14h 23m

$612

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 27 results
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Best time to book a flight from Trinidad and Tobago to Wisconsin

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

Reviews of airlines servicing Wisconsin

Get insights into the airlines that provide service to Wisconsin. 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 Wisconsin. Reviews last updated September 15, 2025.
Read reviews from past customers who have flown United Airlines from Trinidad and Tobago to Wisconsin. 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.
United Airlines
7.4
Good
8,929 reviews

Crew

8.1

Boarding

7.7

Entertainment

7.1

Food

6.6

Comfort

7.3

Overall

7.4

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

FRA - SFO

Lufthansa was amazing, I wish United States based airlines operated like them.
United Airlines
7.4
Good
8,929 reviews
United Airlines
7.4
Good
8,929 reviews

Crew

8.1

Boarding

7.7

Entertainment

7.1

Food

6.6

Comfort

7.3

Overall

7.4

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

FRA - SFO

Lufthansa was amazing, I wish United States based airlines operated like them.

Related info for your journey

Find useful and relevant information for your journey from Trinidad and Tobago to Wisconsin. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Trinidad and Tobago to Wisconsin?

    A quick flight from Trinidad and Tobago to Wisconsin can take about 10h 50m. Air Canada provides one of the quickest options available for as low as $562. There are 2697 mi between Trinidad and Tobago and Wisconsin. 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 Trinidad and Tobago to Wisconsin that include hotel bookings?

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

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

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Trinidad and Tobago to Wisconsin.

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

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

    Currently, February is the cheapest month in which you can book a flight from Trinidad and Tobago to Wisconsin (average of $280). Flying from Trinidad and Tobago to Wisconsin in June is currently the most expensive (average of $376). 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 Trinidad and Tobago to Wisconsin

See prices for flight routes from nearby airports that may be better suited for you.
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Top airline flying from Trinidad and Tobago to Wisconsin

Discover the top airline that operate flights from Trinidad and Tobago to Wisconsin. 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
United AirlinesCheapest$636Average$763FlexibilityNo cancel feeOn-time69%

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