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$401+ Cheap flights from Trinidad 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
Nov 5 — Nov 121
Wed 11/5
Wed 11/12
1 adult, Economy
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Cheap flight deals from Trinidad to Wisconsin

Keep the following information in mind while searching for Trinidad to Wisconsin flight deals. Data was last updated October 6, 2025.

Most accurate provider

Expedia
2 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$455
(Kiwi.com)

One-way from

$401
(American Airlines)
Provider with most accurate pricing for Port of Spain Piarco Intl-Milwaukee-Mitchell flight deals.
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Provider most trusted by Cheapflights users for Port of Spain Piarco Intl-Milwaukee-Mitchell flights.
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From Trinidad to Wisconsin
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One-way flight from Trinidad to Wisconsin
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Find flight deals from Trinidad to Wisconsin

Cheapest flights from Trinidad to Wisconsin
Explore the most affordable flight options available from Trinidad to Wisconsin. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 6, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/4. 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 10/242:40 pmPOS - ORD
2 stops18h 38mMultiple Airlines
Sat 11/111:55 amORD - POS
1 stop31h 05mMultiple Airlines
Deal found 10/4$455
This Kiwi.com deal was found by Cheapflights users on 10/4. 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 10/242:40 pmPOS - ORD
2 stops18h 38mMultiple Airlines
Fri 10/315:05 amORD - POS
1 stop13h 55mMultiple Airlines
Deal found 10/4$462
This Mytrip deal was found by Cheapflights users on 10/5. 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 11/2010:10 amPOS - ORD
1 stop15h 03mMultiple Airlines
Thu 11/273:55 pmORD - POS
1 stop31h 15mMultiple Airlines
Deal found 10/5$510
This American Airlines deal was found by Cheapflights users on 10/5. 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
2 stops22h 56mAmerican Airlines
Sat 1/104:52 pmMSP - POS
2 stops20h 33mAmerican Airlines
Deal found 10/5$642
This United Airlines deal was found by Cheapflights users on 10/4. 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 1/106:00 amMSP - POS
2 stops16h 23mUnited Airlines
Deal found 10/4$708
This United Airlines deal was found by Cheapflights users on 10/4. 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 1/27:40 amMSP - POS
2 stops15h 25mUnited Airlines
Deal found 10/4$772
This American Airlines deal was found by Cheapflights users on 10/4. 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 12/234:46 pmPOS - MSP
2 stops22h 12mAmerican Airlines
Fri 1/25:04 pmMSP - POS
2 stops20h 42mAmerican Airlines
Deal found 10/4$845
This United Airlines deal was found by Cheapflights users on 10/3. 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 10/312:30 amPOS - MKE
1 stop17h 38mUnited Airlines
Sat 10/188:00 amMKE - POS
1 stop14h 23mUnited Airlines
Deal found 10/3$901

Cheapflights Fare Finder

 
Customize your flight search to find flights from Trinidad 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 October 6, 2025.
Use the filters below to find and compare flights from Trinidad to Wisconsin that are best for you.

Fly from

Trinidad

Fly to

Wisconsin

Route

Depart

Return

Price

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Fri 10/24

2:40 pm-8:18 am

2 stops18h 38m

Chicago O'Hare Intl

Sat 11/1

11:55 am-8:00 pm

1 stop31h 05m

$455

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Fri 10/24

2:40 pm-8:18 am

2 stops18h 38m

Chicago O'Hare Intl

Fri 10/31

5:05 am-8:00 pm

1 stop13h 55m

$462

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Thu 11/20

10:10 am-11:13 pm

1 stop15h 03m

Chicago O'Hare Intl

Thu 11/27

3:55 pm-1:10 am

1 stop31h 15m

$510

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Thu 2/26

2:15 am-3:10 pm

1 stop14h 55m

Chicago O'Hare Intl

Tue 3/3

10:35 am-1:10 am

2 stops12h 35m

$539

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

8:00 am-12:23 am

1 stop14h 23m

$625

Port of SpainMinneapolis

POS - MSP

POSMSP

Port of Spain Piarco Intl

Sat 12/13

4:33 pm-11:28 am

2 stops20h 55m

Minneapolis St Paul

Sat 1/10

7:43 am-10:48 pm

2 stops13h 05m

$642

Port of SpainMinneapolis

POS - MSP

POSMSP

Port of Spain Piarco Intl

Fri 12/12

1:30 am-7:40 pm

2 stops20h 10m

Minneapolis St Paul

Sat 1/10

6:00 am-12:23 am

2 stops16h 23m

$708

Port of SpainMinneapolis

POS - MSP

POSMSP

Port of Spain Piarco Intl

Mon 12/22

1:30 am-3:48 pm

2 stops16h 18m

Minneapolis St Paul

Fri 1/2

7:40 am-1:05 am

2 stops15h 25m

$772

Port of SpainMilwaukee

POS - MKE

POSMKE

Port of Spain Piarco Intl

Sat 2/28

4:40 pm-9:50 am

2 stops43h 10m

Milwaukee-Mitchell

Tue 3/3

6:50 pm-3:05 pm

2 stops18h 15m

$804

Port of SpainMinneapolis

POS - MSP

POSMSP

Port of Spain Piarco Intl

Tue 12/23

6:02 am-11:59 pm

1 stop19h 57m

$401

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/4

Showing 1-10 of 11 results
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Best time to book a flight from Trinidad to Wisconsin

Have a flexible travel schedule? Discover the best time to fly to Wisconsin from Trinidad 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 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 October 6, 2025.
Peruse reviews from past customers who have flown with United Airlines from Trinidad to Wisconsin to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
8,953 reviews

Crew

8.1

Overall

7.4

Entertainment

7.1

Comfort

7.3

Boarding

7.7

Food

6.6

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
United Airlines
7.4
Good
8,953 reviews
United Airlines
7.4
Good
8,953 reviews

Crew

8.1

Overall

7.4

Entertainment

7.1

Comfort

7.3

Boarding

7.7

Food

6.6

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.

Related info for your journey

Find useful and relevant information for your journey from Trinidad 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 to Wisconsin?

    United Airlines and American Airlines can get you from Trinidad to Wisconsin in just under 10h 38m. Your travel time can differ by up to 10h 17m. Airlines will cover a distance of 2744 mi. 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 to Wisconsin that include hotel bookings?

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

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

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

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

    Yes. Cheapflights offers flight deals from Trinidad 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 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 to Wisconsin

Discover the top airline that operate flights from Trinidad 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 October 6, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$636Average$763FlexibilityNo cancel feeOn-time69%

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