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$248+ 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 12/12. Fares are subject to change and may not be available on all flights or dates of travel.
POS — MKE
Dec 4 — Dec 111
Thu 12/4
Thu 12/11
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 November 4, 2025.

Most accurate provider

Expedia
2 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$463
(Priceline)

One-way from

$255
(Mytrip)
Provider with most accurate pricing for Port of Spain Piarco Intl-Milwaukee-Mitchell flight deals.
Search Deals
Provider most trusted by Cheapflights users for Port of Spain Piarco Intl-Milwaukee-Mitchell flights.
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From Trinidad and Tobago to Wisconsin
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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 November 4, 2025.

This Air Canada deal was found by Cheapflights users on 11/2. 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.
Tue 11/252:15 amPOS - ORD
2 stops14h 40mAir Canada
Mon 12/18:15 pmORD - POS
1 stop26h 55mAir Canada
Deal found 11/2$471
This American Airlines deal was found by Cheapflights users on 11/2. 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 11/267:19 amPOS - ORD
1 stop12h 58mAmerican Airlines
Mon 12/17:17 pmORD - POS
1 stop18h 13mAmerican Airlines
Deal found 11/2$574
This American Airlines deal was found by Cheapflights users on 11/2. 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 11/237:19 amPOS - ORD
1 stop19h 18mAmerican Airlines
Sun 11/307:17 pmORD - POS
1 stop18h 13mAmerican Airlines
Deal found 11/2$580
This United Airlines deal was found by Cheapflights users on 11/3. 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 50mUnited Airlines
Sat 1/106:15 amMSP - POS
1 stop16h 08mUnited Airlines
Deal found 11/3$647
This American Airlines deal was found by Cheapflights users on 11/3. 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 1/104:47 pmMSP - POS
2 stops20h 38mAmerican Airlines
Deal found 11/3$665
This Mytrip deal was found by Cheapflights users on 11/3. 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 12/189:10 amPOS - ORD
1 stop9h 50mMultiple Airlines
Thu 12/257:57 pmORD - POS
2 stops22h 03mMultiple Airlines
Deal found 11/3$669
This United Airlines deal was found by Cheapflights users on 11/2. 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 11/221:30 amPOS - ORD
1 stop10h 32mUnited Airlines
Sun 11/306:00 amORD - POS
1 stop16h 23mUnited Airlines
Deal found 11/2$672
This American Airlines deal was found by Cheapflights users on 11/3. 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.
Tue 12/236:02 amPOS - MSP
1 stop19h 57mAmerican Airlines
Fri 1/25:04 pmMSP - POS
2 stops20h 42mAmerican Airlines
Deal found 11/3$733
This United Airlines deal was found by Cheapflights users on 11/2. 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 stops23h 14mUnited Airlines
Fri 1/26:45 pmMSP - POS
2 stops27h 38mUnited Airlines
Deal found 11/2$772

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 November 4, 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

Fri 2/13

2:20 am-6:52 pm

2 stops18h 32m

Chicago O'Hare Intl

Tue 2/17

7:15 am-1:20 am

2 stops16h 05m

$463

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Tue 1/13

2:20 am-6:51 pm

2 stops18h 31m

Chicago O'Hare Intl

Tue 1/20

7:15 am-1:20 am

2 stops16h 05m

$463

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Tue 11/25

2:15 am-3:10 pm

1 stop14h 55m

Chicago O'Hare Intl

Mon 12/1

8:15 pm-1:10 am

1 stop26h 55m

$471

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Thu 2/26

2:20 am-6:52 pm

2 stops42h 32m

Chicago O'Hare Intl

Tue 3/3

2:00 pm-1:20 am

1 stop9h 20m

$483

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Wed 1/14

2:16 pm-12:24 am

1 stop12h 08m

Chicago O'Hare Intl

Tue 1/20

7:35 am-1:44 am

1 stop16h 09m

$562

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Wed 11/26

7:19 am-6:17 pm

1 stop12h 58m

Chicago O'Hare Intl

Mon 12/1

7:17 pm-3:30 pm

1 stop18h 13m

$574

Port of SpainMinneapolis

POS - MSP

POSMSP

Port of Spain Piarco Intl

Thu 3/12

12:30 am-5:01 pm

2 stops17h 31m

Minneapolis St Paul

Sun 3/15

8:00 am-11:23 pm

2 stops38h 23m

$611

Port of SpainMilwaukee

POS - MKE

POSMKE

Port of Spain Piarco Intl

Fri 2/27

2:20 am-10:58 am

1 stop10h 38m

Milwaukee-Mitchell

Tue 3/3

8:28 am-12:23 am

2 stops13h 55m

$625

Port of SpainMinneapolis

POS - MSP

POSMSP

Port of Spain Piarco Intl

Fri 3/13

3:34 pm-12:27 pm

2 stops21h 53m

Minneapolis St Paul

Sun 3/15

4:11 pm-1:51 pm

2 stops20h 40m

$642

Port of SpainMinneapolis

POS - MSP

POSMSP

Port of Spain Piarco Intl

Fri 12/12

1:30 am-1:20 pm

1 stop13h 50m

Minneapolis St Paul

Sat 1/10

6:15 am-12:23 am

1 stop16h 08m

$647

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/3

Showing 1-10 of 24 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 November 4, 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
8,997 reviews

Comfort

7.3

Food

6.6

Overall

7.4

Crew

8.1

Entertainment

7.1

Boarding

7.7

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000
United Airlines
7.4
Good
8,997 reviews
United Airlines
7.4
Good
8,997 reviews

Comfort

7.3

Food

6.6

Overall

7.4

Crew

8.1

Entertainment

7.1

Boarding

7.7

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000

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 17h 31m. Air Canada provides one of the quickest options available for as low as $611. There are 3027 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.

  • What are the cheapest airlines to fly from Trinidad and Tobago to Wisconsin one-way?

    The cheapest airlines for a one-way flight from Trinidad and Tobago to Wisconsin are Air Canada ($265), American Airlines ($401), and United Airlines ($405).

  • 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.

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 November 4, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$636Average$771FlexibilityNo cancel feeOn-time69%

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