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Wisconsin

$446+ Cheap flights from Trinidad 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 1/13. Fares are subject to change and may not be available on all flights or dates of travel.
POS — MKE
Feb 10 — Feb 171
Tue 2/10
Tue 2/17
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 January 11, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$522
(Kiwi.com)
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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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 January 11, 2026.

This Priceline deal was found by Cheapflights users on 1/10. 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.
Tue 1/132:20 amPOS - ORD
2 stops18h 35mAir Canada
Mon 1/198:45 pmORD - POS
1 stop26h 35mAir Canada
Deal found 1/10$446
This Expedia deal was found by Cheapflights users on 1/11. 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 2/18:20 amPOS - ORD
2 stops35h 23mMultiple Airlines
Mon 2/166:04 pmORD - POS
2 stops29h 16mMultiple Airlines
Deal found 1/11$452
This Air Canada deal was found by Cheapflights users on 1/11. 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.
Fri 8/211:25 amPOS - ORD
1 stop12h 57mAir Canada
Mon 8/312:15 pmORD - POS
1 stop9h 00mAir Canada
Deal found 1/11$453
This Air Canada deal was found by Cheapflights users on 1/11. 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 2/12:20 amPOS - ORD
1 stop12h 41mAir Canada
Sun 2/1510:00 amORD - POS
1 stop13h 20mAir Canada
Deal found 1/11$464
This Booking.com deal was found by Cheapflights users on 1/10. 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 1/112:20 amPOS - ORD
1 stop19h 25mAir Canada
Sat 1/178:40 pmORD - POS
1 stop26h 40mAir Canada
Deal found 1/10$502
This Kiwi.com deal was found by Cheapflights users on 1/8. 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 3/19:10 amPOS - ORD
1 stop27h 18mMultiple Airlines
Sat 3/712:25 pmORD - POS
1 stop29h 35mMultiple Airlines
Deal found 1/8$522
This Kiwi.com deal was found by Cheapflights users on 1/11. 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 2/243:13 amPOS - ORD
2 stops14h 39mMultiple Airlines
Wed 3/47:23 pmORD - POS
1 stop21h 32mMultiple Airlines
Deal found 1/11$536
This Kiwi.com deal was found by Cheapflights users on 1/9. 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 2/233:13 amPOS - ORD
2 stops38h 35mMultiple Airlines
Tue 3/37:23 pmORD - POS
1 stop21h 32mMultiple Airlines
Deal found 1/9$542
This United Airlines deal was found by Cheapflights users on 1/9. 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 4/112:30 amPOS - MSP
1 stop11h 22mUnited Airlines
Thu 4/307:30 amMSP - POS
1 stop14h 53mUnited Airlines
Deal found 1/9$613
This United Airlines deal was found by Cheapflights users on 1/9. 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.
Thu 4/212:30 amPOS - MSP
1 stop11h 22mUnited Airlines
Fri 5/18:15 amMSP - POS
2 stops14h 08mUnited Airlines
Deal found 1/9$636
This United Airlines deal was found by Cheapflights users on 1/9. 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 4/112:30 amPOS - MSP
1 stop11h 22mUnited Airlines
Fri 5/18:15 amMSP - POS
2 stops14h 08mUnited Airlines
Deal found 1/9$637
This Booking.com deal was found by Cheapflights users on 1/9. 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.
Fri 7/101:25 amPOS - MSP
1 stop12h 05mAir Canada
Sat 7/181:10 pmMSP - POS
2 stops34h 05mAir Canada
Deal found 1/9$641

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 January 11, 2026.
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

Sun 2/1

8:20 am-5:43 pm

2 stops35h 23m

Chicago O'Hare Intl

Mon 2/16

6:04 pm-1:20 am

2 stops29h 16m

$452

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Sun 2/1

2:20 am-7:45 pm

1 stop19h 25m

Chicago O'Hare Intl

Wed 2/18

8:40 pm-1:20 am

1 stop26h 40m

$464

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Sun 2/1

2:20 am-7:45 pm

1 stop19h 25m

Chicago O'Hare Intl

Mon 2/16

6:04 pm-1:20 am

2 stops29h 16m

$464

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Sun 2/1

2:20 am-1:01 pm

1 stop12h 41m

Chicago O'Hare Intl

Tue 2/17

6:04 pm-1:20 am

2 stops53h 16m

$464

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Sun 2/1

2:20 am-1:01 pm

1 stop12h 41m

Chicago O'Hare Intl

Sun 2/15

10:00 am-1:20 am

1 stop13h 20m

$464

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Sun 2/1

2:20 am-3:10 pm

1 stop14h 50m

Chicago O'Hare Intl

Sat 2/14

8:40 pm-1:20 am

1 stop26h 40m

$464

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Sun 3/1

9:10 am-10:28 am

1 stop27h 18m

Chicago O'Hare Intl

Sat 3/7

12:25 pm-8:00 pm

1 stop29h 35m

$522

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Tue 2/24

3:13 am-3:52 pm

2 stops14h 39m

Chicago O'Hare Intl

Wed 3/4

7:23 pm-6:55 pm

1 stop21h 32m

$536

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Mon 2/23

3:13 am-3:48 pm

2 stops38h 35m

Chicago O'Hare Intl

Tue 3/3

7:23 pm-6:55 pm

1 stop21h 32m

$542

Port of SpainMinneapolis

POS - MSP

POSMSP

Port of Spain Piarco Intl

Thu 4/2

12:30 am-10:52 am

1 stop11h 22m

Minneapolis St Paul

Thu 4/30

12:05 pm-11:23 pm

1 stop10h 18m

$613

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/11

Showing 1-10 of 19 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 January 11, 2026.
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
9,143 reviews

Entertainment

7.1

Boarding

7.7

Comfort

7.3

Overall

7.4

Crew

8.1

Food

6.6

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family
United Airlines
7.4
Good
9,143 reviews
United Airlines
7.4
Good
9,143 reviews

Entertainment

7.1

Boarding

7.7

Comfort

7.3

Overall

7.4

Crew

8.1

Food

6.6

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family

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?

    Air Canada and United Airlines can get you from Trinidad to Wisconsin in just under 11h 22m. Your travel time can differ by up to 8h 03m. Airlines will cover a distance of 3027 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 January 11, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$636Average$763FlexibilityNo cancel feeOn-time69%

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