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$308+ 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 5/27. Fares are subject to change and may not be available on all flights or dates of travel.
POS — MKE
May 5 — May 121
Mon 5/5
Mon 5/12
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 April 30, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$550
(Air Canada)

One-way from

$308
(United Airlines)
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.
Search Deals
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 April 30, 2025.

This Air Canada deal was found by Cheapflights users on 4/29. 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.
Sun 7/62:25 amPOS - ORD
1 stop11h 28mAir Canada
Fri 7/182:00 pmORD - POS
1 stop10h 25mAir Canada
Deal found 4/29$550
This Copa Airlines deal was found by Cheapflights users on 4/28. 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 7/13:48 amPOS - ORD
1 stop10h 54mCopa Airlines
Wed 8/137:54 amORD - POS
1 stop16h 54mCopa Airlines
Deal found 4/28$551
This United Airlines deal was found by Cheapflights users on 4/28. 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 5/1912:30 amPOS - ORD
1 stop24h 45mUnited Airlines
Tue 6/39:21 amORD - POS
1 stop13h 02mUnited Airlines
Deal found 4/28$561
This American Airlines deal was found by Cheapflights users on 4/29. 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 7/27:09 amPOS - ORD
2 stops15h 16mAmerican Airlines
Wed 8/1310:35 amORD - POS
2 stops10h 01mAmerican Airlines
Deal found 4/29$567
This Kiwi.com deal was found by Cheapflights users on 4/27. 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.
Tue 5/209:10 amPOS - ORD
1 stop9h 31mMultiple Airlines
Tue 6/35:51 amORD - POS
2 stops12h 04mMultiple Airlines
Deal found 4/27$658

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 April 30, 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

Sun 7/6

2:25 am-12:53 pm

1 stop11h 28m

Chicago O'Hare Intl

Fri 7/18

2:00 pm-1:25 am

1 stop10h 25m

$550

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Tue 7/1

3:48 am-1:42 pm

1 stop10h 54m

Chicago O'Hare Intl

Wed 8/13

7:54 am-1:48 am

1 stop16h 54m

$551

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Mon 5/19

12:30 am-12:15 am

1 stop24h 45m

Chicago O'Hare Intl

Tue 6/3

9:21 am-11:23 pm

1 stop13h 02m

$561

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Wed 7/2

7:09 am-9:25 pm

2 stops15h 16m

Chicago O'Hare Intl

Wed 8/13

10:35 am-9:36 pm

2 stops10h 01m

$567

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Tue 5/20

9:10 am-5:41 pm

1 stop9h 31m

Chicago O'Hare Intl

Tue 6/3

5:51 am-6:55 pm

2 stops12h 04m

$658

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Tue 5/27

12:30 am-9:55 am

1 stop10h 25m

$308

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Thu 5/29

3:15 pm-6:26 am

2 stops16h 11m

$318

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Wed 5/28

9:10 am-5:41 pm

1 stop9h 31m

$343

Port of SpainMinneapolis

POS - MSP

POSMSP

Port of Spain Piarco Intl

Wed 5/21

12:30 am-10:49 am

1 stop11h 19m

$421

Port of SpainMinneapolis

POS - MSP

POSMSP

Port of Spain Piarco Intl

Thu 5/22

3:15 pm-10:46 pm

1 stop32h 31m

$549

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

Showing 1-10 of 11 results
1
2

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

Rainfall in Wisconsin by month

Plan your trip to Wisconsin by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Wisconsin ranges from 1.4 - 4.0 inches per month. June is typically the wettest month, when rainfall can reach 4.0 in. January is typically the driest time to visit Wisconsin when rainfall is around 1.4 in.

Temperature in Wisconsin by month

Plan your trip to Wisconsin by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Wisconsin, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 21.2 F).

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 April 30, 2025.
Copa Airlines
7.5
Good
1,411 reviews

Entertainment

6.7

Comfort

7.4

Crew

8.1

Overall

7.5

Boarding

7.8

Food

6.8

Reviews

1 / 20
4.0
Okay

Anonymous,Mar 2025

PTY - JFK

There was no chance for me to choose a seat even if I were willing to pay extra for it when I was doing the check-in on line. My seats were the last row on the plane and they didn't have enough food to give me. I had to eat what was left after everybody else had their choice of food. This is unacceptable. Everyone should have a choice. I paid money just like everybody else. Never had this happened on any other airlines even if my seats were last row on the plane.
Copa Airlines
7.5
Good
1,411 reviews
Copa Airlines
7.5
Good
1,411 reviews

Entertainment

6.7

Comfort

7.4

Crew

8.1

Overall

7.5

Boarding

7.8

Food

6.8

Reviews

1 / 20
4.0
Okay

Anonymous,Mar 2025

PTY - JFK

There was no chance for me to choose a seat even if I were willing to pay extra for it when I was doing the check-in on line. My seats were the last row on the plane and they didn't have enough food to give me. I had to eat what was left after everybody else had their choice of food. This is unacceptable. Everyone should have a choice. I paid money just like everybody else. Never had this happened on any other airlines even if my seats were last row on the plane.
United Airlines
7.4
Good
8,696 reviews
Copa Airlines
7.5
Good
1,411 reviews

Entertainment

6.7

Comfort

7.4

Crew

8.1

Overall

7.5

Boarding

7.8

Food

6.8

Reviews

1 / 20
4.0
Okay

Anonymous,Mar 2025

PTY - JFK

There was no chance for me to choose a seat even if I were willing to pay extra for it when I was doing the check-in on line. My seats were the last row on the plane and they didn't have enough food to give me. I had to eat what was left after everybody else had their choice of food. This is unacceptable. Everyone should have a choice. I paid money just like everybody else. Never had this happened on any other airlines even if my seats were last row on the plane.
American Airlines
7.2
Good
10,000 reviews
Copa Airlines
7.5
Good
1,411 reviews

Entertainment

6.7

Comfort

7.4

Crew

8.1

Overall

7.5

Boarding

7.8

Food

6.8

Reviews

1 / 20
4.0
Okay

Anonymous,Mar 2025

PTY - JFK

There was no chance for me to choose a seat even if I were willing to pay extra for it when I was doing the check-in on line. My seats were the last row on the plane and they didn't have enough food to give me. I had to eat what was left after everybody else had their choice of food. This is unacceptable. Everyone should have a choice. I paid money just like everybody else. Never had this happened on any other airlines even if my seats were last row on the plane.
Air Canada
7.0
Good
9,244 reviews
Copa Airlines
7.5
Good
1,411 reviews

Entertainment

6.7

Comfort

7.4

Crew

8.1

Overall

7.5

Boarding

7.8

Food

6.8

Reviews

1 / 20
4.0
Okay

Anonymous,Mar 2025

PTY - JFK

There was no chance for me to choose a seat even if I were willing to pay extra for it when I was doing the check-in on line. My seats were the last row on the plane and they didn't have enough food to give me. I had to eat what was left after everybody else had their choice of food. This is unacceptable. Everyone should have a choice. I paid money just like everybody else. Never had this happened on any other airlines even if my seats were last row on the plane.

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.

  • 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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