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$444+ Cheap flights from Trinidad and Tobago to Wisconsin

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 2/12. Fares are subject to change and may not be available on all flights or dates of travel.
POS — MKE
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
1 adult, Economy
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Cheap 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 December 18, 2025.

This Priceline deal was found by Cheapflights users on 12/16. 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.
Thu 12/252:15 amPOS - ORD
1 stop12h 46mAir Canada
Tue 12/302:00 pmORD - POS
1 stop9h 10mAir Canada
Deal found 12/16$669
This Gotogate deal was found by Cheapflights users on 12/16. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/252:15 amPOS - ORD
2 stops19h 55mMultiple Airlines
Tue 12/308:30 pmORD - POS
2 stops20h 55mMultiple Airlines
Deal found 12/16$758
This United Airlines deal was found by Cheapflights users on 12/17. 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.
Mon 12/221:30 amPOS - MSP
2 stops38h 46mUnited Airlines
Fri 1/25:16 pmMSP - POS
2 stops29h 07mUnited Airlines
Deal found 12/17$963
This United Airlines deal was found by Cheapflights users on 12/16. 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.
Wed 12/171:30 amPOS - ORD
1 stop15h 10mUnited Airlines
Tue 12/237:35 amORD - POS
1 stop14h 48mUnited Airlines
Deal found 12/16$1,001
This Kiwi.com deal was found by Cheapflights users on 12/17. 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.
Sun 12/217:35 pmPOS - ORD
1 stop23h 25mMultiple Airlines
Tue 12/237:01 pmORD - POS
2 stops29h 12mMultiple Airlines
Deal found 12/17$1,025
This Expedia deal was found by Cheapflights users on 12/17. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/213:55 pmPOS - ORD
2 stops28h 51mJetBlue
Tue 12/237:41 pmORD - POS
2 stops16h 49mJetBlue
Deal found 12/17$1,057
This American Airlines deal was found by Cheapflights users on 12/17. 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.
Tue 12/234:46 pmPOS - MSP
2 stops20h 26mAmerican Airlines
Fri 1/25:48 amMSP - POS
1 stop15h 59mAmerican Airlines
Deal found 12/17$1,084
This United Airlines deal was found by Cheapflights users on 12/17. 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 12/202:20 amPOS - ORD
1 stop11h 45mUnited Airlines
Tue 12/231:37 pmORD - POS
1 stop9h 28mUnited Airlines
Deal found 12/17$1,085
This American Airlines deal was found by Cheapflights users on 12/16. 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.
Thu 12/186:02 amPOS - ORD
2 stops13h 47mAmerican Airlines
Tue 12/237:11 amORD - POS
2 stops14h 35mAmerican Airlines
Deal found 12/16$1,630

Find 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 December 18, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$444
(Expedia)
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
Search Deals

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 December 18, 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

Thu 2/12

8:50 am-11:10 pm

1 stop16h 20m

Chicago O'Hare Intl

Thu 2/19

10:00 am-7:17 am

2 stops19h 17m

$444

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Fri 1/30

8:20 am-5:43 pm

2 stops35h 23m

Chicago O'Hare Intl

Fri 2/6

10:00 am-1:20 am

1 stop13h 20m

$478

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Thu 2/12

12:22 pm-11:10 pm

1 stop12h 48m

Chicago O'Hare Intl

Thu 2/19

2:00 pm-1:20 am

1 stop9h 20m

$480

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Thu 1/29

2:20 am-3:10 pm

1 stop14h 50m

Chicago O'Hare Intl

Fri 2/6

10:00 am-1:20 am

1 stop13h 20m

$513

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Sun 2/1

8:20 am-6:32 pm

1 stop12h 12m

Chicago O'Hare Intl

Sun 2/8

10:00 am-1:20 am

1 stop13h 20m

$529

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Wed 5/6

2:22 pm-1:15 am

1 stop11h 53m

Chicago O'Hare Intl

Sun 5/10

8:02 am-1:46 am

1 stop16h 44m

$584

Port of SpainMinneapolis

POS - MSP

POSMSP

Port of Spain Piarco Intl

Thu 1/22

1:30 am-1:00 pm

1 stop13h 30m

Minneapolis St Paul

Sun 1/25

7:35 am-12:23 am

1 stop14h 48m

$613

Port of SpainMinneapolis

POS - MSP

POSMSP

Port of Spain Piarco Intl

Thu 1/15

6:30 am-11:59 pm

1 stop19h 29m

Minneapolis St Paul

Thu 1/29

6:00 am-10:48 pm

1 stop14h 48m

$613

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Wed 5/6

3:10 pm-8:49 am

2 stops18h 39m

Chicago O'Hare Intl

Sun 5/10

7:17 pm-2:00 pm

1 stop17h 43m

$640

Port of SpainMinneapolis

POS - MSP

POSMSP

Port of Spain Piarco Intl

Sun 1/11

1:30 am-2:23 pm

2 stops14h 53m

Minneapolis St Paul

Sun 1/25

5:16 pm-12:23 am

2 stops29h 07m

$661

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/17

Showing 1-10 of 25 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 December 18, 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
9,091 reviews

Comfort

7.3

Entertainment

7.1

Boarding

7.7

Crew

8.1

Overall

7.4

Food

6.6

Reviews

1 / 20
4.0
Okay

Kevin,Dec 2025

BOS - EWR

Seems like every United flight has a delay and it’s always someone else’s fault. Step up and take some accountability
United Airlines
7.4
Good
9,091 reviews
United Airlines
7.4
Good
9,091 reviews

Comfort

7.3

Entertainment

7.1

Boarding

7.7

Crew

8.1

Overall

7.4

Food

6.6

Reviews

1 / 20
4.0
Okay

Kevin,Dec 2025

BOS - EWR

Seems like every United flight has a delay and it’s always someone else’s fault. Step up and take some accountability

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 13h 30m. JetBlue provides one of the quickest options available for as low as $613. 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.

  • 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 December 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$636Average$771FlexibilityNo cancel feeOn-time69%

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