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$400+ 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 12/23. Fares are subject to change and may not be available on all flights or dates of travel.
POS — MKE
Oct 19 — Oct 261
Sun 10/19
Sun 10/26
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 19, 2025.

Round-trip from

$452
(Priceline)

One-way from

$400
(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 19, 2025.

This Priceline deal was found by Cheapflights users on 9/17. 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.
Sun 10/261:15 amPOS - ORD
2 stops18h 40mAir Canada
Thu 10/302:00 pmORD - POS
1 stop9h 10mAir Canada
Deal found 9/17$452
This Kiwi.com deal was found by Cheapflights users on 9/17. 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.
Thu 10/166:25 pmPOS - ORD
1 stop15h 57mMultiple Airlines
Thu 10/2310:27 amORD - POS
2 stops14h 19mMultiple Airlines
Deal found 9/17$458
This Booking.com deal was found by Cheapflights users on 9/17. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/162:15 amPOS - ORD
2 stops42h 40mAir Canada
Sat 12/66:05 pmORD - POS
2 stops29h 05mAir Canada
Deal found 9/17$471
This Kiwi.com deal was found by Cheapflights users on 9/17. 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.
Fri 10/172:40 pmPOS - ORD
2 stops18h 38mMultiple Airlines
Sun 10/1910:27 amORD - POS
1 stop16h 48mMultiple Airlines
Deal found 9/17$506
This Kiwi.com deal was found by Cheapflights users on 9/17. 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 11/1710:10 amPOS - ORD
1 stop25h 13mMultiple Airlines
Sat 12/65:59 pmORD - POS
2 stops41h 32mMultiple Airlines
Deal found 9/17$523
This Kiwi.com deal was found by Cheapflights users on 9/18. 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 9/303:51 amPOS - ORD
2 stops30h 27mMultiple Airlines
Tue 10/146:58 pmORD - POS
1 stop23h 32mMultiple Airlines
Deal found 9/18$551
This Copa Airlines deal was found by Cheapflights users on 9/17. 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.
Wed 10/153:51 amPOS - ORD
1 stop10h 50mCopa Airlines
Thu 10/233:07 pmORD - POS
1 stop9h 39mCopa Airlines
Deal found 9/17$562
This Kiwi.com deal was found by Cheapflights users on 9/17. 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.
Sat 11/13:48 amPOS - MSP
2 stops18h 05mMultiple Airlines
Sun 11/96:18 amMSP - POS
1 stop10h 37mMultiple Airlines
Deal found 9/17$578
This United Airlines deal was found by Cheapflights users on 9/17. 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 11/11:32 amPOS - MSP
2 stops33h 22mUnited Airlines
Sun 11/911:27 amMSP - POS
2 stops34h 56mUnited Airlines
Deal found 9/17$633
This United Airlines deal was found by Cheapflights users on 9/17. 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 9/17$637
This American Airlines deal was found by Cheapflights users on 9/17. 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 11/27:19 amPOS - MSP
1 stop17h 55mAmerican Airlines
Sun 11/95:45 amMSP - POS
1 stop15h 54mAmerican Airlines
Deal found 9/17$653
This American Airlines deal was found by Cheapflights users on 9/18. 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 1/106:18 pmMSP - POS
2 stops18h 47mAmerican Airlines
Deal found 9/18$655

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 19, 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 10/26

1:15 am-6:55 pm

2 stops18h 40m

Chicago O'Hare Intl

Thu 10/30

7:15 am-12:10 am

2 stops15h 55m

$452

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Sun 11/16

2:15 am-2:55 pm

2 stops14h 40m

Chicago O'Hare Intl

Sat 12/6

8:15 pm-1:10 am

1 stop26h 55m

$452

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Thu 10/16

6:25 pm-9:22 am

1 stop15h 57m

Chicago O'Hare Intl

Thu 10/23

10:27 am-1:46 am

2 stops14h 19m

$458

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Fri 10/17

2:40 pm-8:18 am

2 stops18h 38m

Chicago O'Hare Intl

Sun 10/19

10:27 am-4:15 am

1 stop16h 48m

$506

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Mon 11/17

10:10 am-9:23 am

1 stop25h 13m

Chicago O'Hare Intl

Sat 12/6

5:59 pm-1:31 pm

2 stops41h 32m

$523

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Wed 10/15

3:51 am-1:41 pm

1 stop10h 50m

Chicago O'Hare Intl

Thu 10/23

3:07 pm-1:46 am

1 stop9h 39m

$562

Port of SpainMinneapolis

POS - MSP

POSMSP

Port of Spain Piarco Intl

Sun 11/2

10:10 am-10:34 am

2 stops26h 24m

Minneapolis St Paul

Sun 11/9

6:48 am-1:05 pm

1 stop28h 17m

$599

Port of SpainMilwaukee

POS - MKE

POSMKE

Port of Spain Piarco Intl

Fri 2/27

2:20 am-6:47 pm

2 stops18h 27m

Milwaukee-Mitchell

Tue 3/3

11:39 am-1:05 am

1 stop11h 26m

$629

Port of SpainMinneapolis

POS - MSP

POSMSP

Port of Spain Piarco Intl

Sat 11/1

1:32 am-9:54 am

2 stops33h 22m

Minneapolis St Paul

Sun 11/9

11:27 am-12:23 am

2 stops34h 56m

$633

Port of SpainMinneapolis

POS - MSP

POSMSP

Port of Spain Piarco Intl

Fri 12/12

1:30 am-1:10 pm

1 stop13h 40m

Minneapolis St Paul

Sat 1/10

7:35 am-12:23 am

1 stop14h 48m

$637

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/17

Showing 1-10 of 20 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
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 19, 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
8,925 reviews

Comfort

7.3

Overall

7.4

Crew

8.1

Boarding

7.7

Entertainment

7.1

Food

6.6

Reviews

1 / 20
4.0
Okay

Tim,Sep 2025

IAD - GSP

This was pretty bad. It’s chaos at the Dulles boarding gates for the small regional jets because they use one gate to board 3-4 flights at a time. So, it’s difficult knowing where and when to go. There is little space for any size of carrry-on, so most had to gate check their bags. However, the worst of it was that our single flight attendant fell asleep before we took off and the pilot couldn’t do so until she responded to his messages. My wife had to wake her up! So we were a little late leaving. Not to be thwarted, the flight attendant fell asleep right after take off and there was no sight of her during the flight. When the aircraft touched down, a tray of unsecured canned drinks came crashing onto the aisle up front. I can only assume someone didn’t do what they were supposed to. The pilot was great, but I’m sure he must not be happy with this crew member.
United Airlines
7.4
Good
8,925 reviews
United Airlines
7.4
Good
8,925 reviews

Comfort

7.3

Overall

7.4

Crew

8.1

Boarding

7.7

Entertainment

7.1

Food

6.6

Reviews

1 / 20
4.0
Okay

Tim,Sep 2025

IAD - GSP

This was pretty bad. It’s chaos at the Dulles boarding gates for the small regional jets because they use one gate to board 3-4 flights at a time. So, it’s difficult knowing where and when to go. There is little space for any size of carrry-on, so most had to gate check their bags. However, the worst of it was that our single flight attendant fell asleep before we took off and the pilot couldn’t do so until she responded to his messages. My wife had to wake her up! So we were a little late leaving. Not to be thwarted, the flight attendant fell asleep right after take off and there was no sight of her during the flight. When the aircraft touched down, a tray of unsecured canned drinks came crashing onto the aisle up front. I can only assume someone didn’t do what they were supposed to. The pilot was great, but I’m sure he must not be happy with this crew member.

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 18h 01m. Air Canada provides one of the quickest options available for as low as $642. 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 American Airlines ($400), United Airlines ($411), and Copa Airlines ($723).

  • 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 19, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$636Average$763FlexibilityNo cancel feeOn-time69%

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