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$255+ Cheap flights from Port of Spain (POS) 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 1/9. Fares are subject to change and may not be available on all flights or dates of travel.
POS — MKE
Dec 3 — Dec 101
Wed 12/3
Wed 12/10
1 adult, Economy
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Find flight deals from Port of Spain to Wisconsin

Cheapest flights from Port of Spain to Wisconsin
Explore the most affordable flight options available from Port of Spain to Wisconsin. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 3, 2025.

This Air Canada deal was found by Cheapflights users on 11/2. 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.
Tue 11/252:15 amPOS - ORD
2 stops14h 40mAir Canada
Mon 12/18:15 pmORD - POS
1 stop26h 55mAir Canada
Deal found 11/2$471
This American Airlines deal was found by Cheapflights users on 11/2. 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 11/267:19 amPOS - ORD
1 stop12h 58mAmerican Airlines
Mon 12/17:17 pmORD - POS
1 stop18h 13mAmerican Airlines
Deal found 11/2$574
This American Airlines deal was found by Cheapflights users on 11/2. 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 11/237:19 amPOS - ORD
1 stop19h 18mAmerican Airlines
Sun 11/307:17 pmORD - POS
1 stop18h 13mAmerican Airlines
Deal found 11/2$580
This United Airlines deal was found by Cheapflights users on 11/2. 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 50mUnited Airlines
Sat 1/106:15 amMSP - POS
1 stop16h 08mUnited Airlines
Deal found 11/2$647
This Kiwi.com deal was found by Cheapflights users on 11/1. 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 12/299:10 amPOS - ORD
1 stop9h 50mMultiple Airlines
Sat 1/36:05 pmORD - POS
1 stop22h 50mMultiple Airlines
Deal found 11/1$655
This Mytrip deal was found by Cheapflights users on 11/3. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/189:10 amPOS - ORD
1 stop9h 50mMultiple Airlines
Thu 12/257:57 pmORD - POS
2 stops22h 03mMultiple Airlines
Deal found 11/3$669
This United Airlines deal was found by Cheapflights users on 11/1. 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.
Sun 12/282:20 amPOS - ORD
1 stop11h 45mUnited Airlines
Sat 1/38:05 pmORD - POS
1 stop26h 18mUnited Airlines
Deal found 11/1$672
This United Airlines deal was found by Cheapflights users on 11/2. 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 stops23h 14mUnited Airlines
Fri 1/26:45 pmMSP - POS
2 stops27h 38mUnited Airlines
Deal found 11/2$772
This American Airlines deal was found by Cheapflights users on 11/2. 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 12/137:10 amPOS - MSP
1 stop17h 39mAmerican Airlines
Sat 1/106:00 amMSP - POS
1 stop14h 48mAmerican Airlines
Deal found 11/2$790
This American Airlines deal was found by Cheapflights users on 11/2. 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 12/236:02 amPOS - MSP
1 stop19h 57mAmerican Airlines
Fri 1/25:48 amMSP - POS
1 stop15h 59mAmerican Airlines
Deal found 11/2$841

Cheap flight deals from Port of Spain to Wisconsin

Keep the following information in mind while searching for Port of Spain to Wisconsin flight deals. Data was last updated November 3, 2025.

Most accurate provider

Expedia
2 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$463
(Priceline)

One-way from

$255
(Mytrip)
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 Port of Spain Piarco Intl to Wisconsin
Search Deals
One-way flight from Port of Spain Piarco Intl to Wisconsin
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Port of Spain 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 November 3, 2025.
Use the filters below to find and compare flights from Port of Spain to Wisconsin that are best for you.

Fly from

Port of Spain

Fly to

Wisconsin

Route

Depart

Return

Price

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Fri 2/13

2:20 am-6:52 pm

2 stops18h 32m

Chicago O'Hare Intl

Tue 2/17

7:15 am-1:20 am

2 stops16h 05m

$463

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Tue 11/25

2:15 am-3:10 pm

1 stop14h 55m

Chicago O'Hare Intl

Mon 12/1

8:15 pm-1:10 am

1 stop26h 55m

$471

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Thu 2/26

2:20 am-6:52 pm

2 stops42h 32m

Chicago O'Hare Intl

Tue 3/3

10:35 am-1:20 am

2 stops12h 45m

$483

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Wed 11/26

7:19 am-6:17 pm

1 stop12h 58m

Chicago O'Hare Intl

Mon 12/1

7:17 pm-3:30 pm

1 stop18h 13m

$574

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Mon 2/2

9:10 am-12:30 pm

1 stop29h 20m

Chicago O'Hare Intl

Fri 2/6

4:35 pm-8:20 pm

2 stops25h 45m

$577

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Sat 2/14

4:47 pm-12:36 am

1 stop9h 49m

Chicago O'Hare Intl

Tue 2/17

9:08 pm-3:30 pm

2 stops16h 22m

$579

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

8:28 am-12:23 am

2 stops13h 55m

$625

Port of SpainMinneapolis

POS - MSP

POSMSP

Port of Spain Piarco Intl

Fri 12/12

1:30 am-1:20 pm

1 stop13h 50m

Minneapolis St Paul

Sat 1/10

6:15 am-12:23 am

1 stop16h 08m

$647

Port of SpainMinneapolis

POS - MSP

POSMSP

Port of Spain Piarco Intl

Sat 12/13

7:10 am-9:39 pm

2 stops16h 29m

Minneapolis St Paul

Sat 1/10

6:32 am-10:48 pm

2 stops14h 16m

$652

Port of SpainMilwaukee

POS - MKE

POSMKE

Port of Spain Piarco Intl

Sat 2/28

4:47 pm-11:02 am

2 stops20h 15m

Milwaukee-Mitchell

Tue 3/3

5:47 pm-3:30 pm

2 stops19h 43m

$753

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/2

Showing 1-10 of 21 results
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Best time to book a flight from Port of Spain to Wisconsin

Have a flexible travel schedule? Discover the best time to fly to Wisconsin from Port of Spain 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 Port of Spain 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 November 3, 2025.
Read through reviews of airlines operating flights from Port of Spain to Wisconsin, such as United Airlines. 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
8,997 reviews

Food

6.6

Overall

7.4

Entertainment

7.1

Crew

8.1

Boarding

7.7

Comfort

7.3

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000
United Airlines
7.4
Good
8,997 reviews
United Airlines
7.4
Good
8,997 reviews

Food

6.6

Overall

7.4

Entertainment

7.1

Crew

8.1

Boarding

7.7

Comfort

7.3

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000

Related info for your journey

Find useful and relevant information for your journey from Port of Spain to Wisconsin. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Port of Spain to Wisconsin?

    For a flight from Port of Spain to Wisconsin, you will be flying from Piarco Intl. Port of Spain Piarco Intl (POS) is just 12.6 mi from the center of the city.

  • How long is the flight from Port of Spain to Wisconsin?

    Air Canada, United Airlines, and American Airlines can get you from Port of Spain to Wisconsin in just under 10h 38m. Your travel time can differ by up to 7h 54m. Port of Spain and Wisconsin are separated by a distance of 2744 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the most popular routes from Port of Spain to Wisconsin?

    When deciding which route to take from Port of Spain to Wisconsin consider Port of Spain Piarco Intl - Chicago O'Hare Intl, Port of Spain Piarco Intl - Minneapolis St Paul or Port of Spain Piarco Intl - Milwaukee-Mitchell as they are the most popular.

  • Can I find deals for flights from Port of Spain to Wisconsin that include hotel bookings?

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

  • How can I find direct flights from Port of Spain to Wisconsin?

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

  • Can I find deals for business class flights from Port of Spain to Wisconsin?

    Yes. Cheapflights offers flight deals from Port of Spain 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 Port of Spain 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 Port of Spain to Wisconsin

Discover the top airline that operate flights from Port of Spain 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 November 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$636Average$771FlexibilityNo cancel feeOn-time69%

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