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$893+ Cheap flights from Port of Spain (POS) to Milwaukee (MKE)

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 2/11. Fares are subject to change and may not be available on all flights or dates of travel.
POS — MKE
Feb 26 — Mar 51
Thu 2/26
Thu 3/5
1 adult, Economy
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Cheap flight deals from Port of Spain to Milwaukee

Cheapest flights from Port of Spain to Milwaukee
Explore the most affordable flight options available from Port of Spain to Milwaukee. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 27, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/26. 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.
Wed 2/118:30 am
POS
-
MKE
1 stop25h 10m
Multiple Airlines
Sun 2/156:37 pm
MKE
-
POS
2 stops23h 23m
Multiple Airlines
Deal found 1/26$893
This American Airlines deal was found by Cheapflights users on 1/26. 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 2/116:30 am
POS
-
MKE
2 stops19h 05m
American Airlines
Sun 2/153:05 pm
MKE
-
POS
2 stops22h 01m
American Airlines
Deal found 1/26$934
This United Airlines deal was found by Cheapflights users on 1/26. 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.
Tue 2/102:20 am
POS
-
MKE
1 stop10h 26m
United Airlines
Sun 2/1511:39 am
MKE
-
POS
1 stop11h 26m
United Airlines
Deal found 1/26$963

Find flight deals from Port of Spain to Milwaukee

Discover tips and strategies to find the most affordable flight options for your journey from Port of Spain (POS) to Milwaukee (MKE). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated January 27, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$893
(Kiwi.com)
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 Milwaukee-Mitchell
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Port of Spain to Milwaukee 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 27, 2026.
Use the filters below to find and compare flights from Port of Spain to Milwaukee that are best for you.

Fly from

Port of Spain

Fly to

Milwaukee

Route

Depart

Return

Price

Port of SpainMilwaukee

POS - MKE

POSMKE

Port of Spain Piarco Intl

Wed 2/11

8:30 am-7:40 am

1 stop25h 10m

Milwaukee-Mitchell

Sun 2/15

6:37 pm-8:00 pm

2 stops23h 23m

$893

Port of SpainMilwaukee

POS - MKE

POSMKE

Port of Spain Piarco Intl

Wed 2/11

6:30 am-11:35 pm

2 stops19h 05m

Milwaukee-Mitchell

Sun 2/15

3:05 pm-3:06 pm

2 stops22h 01m

$934

Port of SpainMilwaukee

POS - MKE

POSMKE

Port of Spain Piarco Intl

Tue 2/10

2:20 am-10:46 am

1 stop10h 26m

Milwaukee-Mitchell

Sun 2/15

11:39 am-1:05 am

1 stop11h 26m

$963

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/26

Compare providers for flights from Port of Spain to Milwaukee

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Port of Spain to Milwaukee in January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Port of Spain-Milwaukee flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Port of Spain-Milwaukee flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Port of Spain-Milwaukee flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Port of Spain-Milwaukee flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Port of Spain-Milwaukee flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Port of Spain to Milwaukee

Have a flexible travel schedule? Discover the best time to fly to Milwaukee 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 Milwaukee

What is the cheapest month to book a flight from Port of Spain to Milwaukee?

Currently, December is the cheapest month in which you can book a flight from Port of Spain to Milwaukee (average of $304). Flying from Port of Spain to Milwaukee in April is currently the most expensive (average of $632). 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.

Reviews of airlines servicing Milwaukee

Get insights into the airlines that provide service to Milwaukee. 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 Milwaukee. Reviews last updated January 27, 2026.
Peruse reviews from past customers who have flown with United Airlines from Port of Spain to Milwaukee 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
9,205 reviews

Boarding

7.7

Crew

8.1

Food

6.6

Comfort

7.3

Overall

7.4

Entertainment

7.1

Reviews

1 / 20
6.0
Good

Gerry,Jan 2026

YVR - DEN

Seats were uncomfortable. Second leg of my flight on United had much more comfortable seats
United Airlines
7.4
Good
9,205 reviews
United Airlines
7.4
Good
9,205 reviews

Boarding

7.7

Crew

8.1

Food

6.6

Comfort

7.3

Overall

7.4

Entertainment

7.1

Reviews

1 / 20
6.0
Good

Gerry,Jan 2026

YVR - DEN

Seats were uncomfortable. Second leg of my flight on United had much more comfortable seats

Related info for your journey

Find useful and relevant information for your journey from Port of Spain to Milwaukee. 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 Port of Spain to Milwaukee?

    American Airlines and United Airlines can get you from Port of Spain to Milwaukee in just under 10h 26m. Your travel time can differ by up to 8h 39m. There are 2744 mi between Port of Spain and Milwaukee. 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 Port of Spain to Milwaukee that include hotel bookings?

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

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

    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 Milwaukee.

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

    Yes. Cheapflights offers flight deals from Port of Spain to Milwaukee 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 Port of Spain to Milwaukee?

    Currently, December is the cheapest month in which you can book a flight from Port of Spain to Milwaukee (average of $304). Flying from Port of Spain to Milwaukee in April is currently the most expensive (average of $632). 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

Traveling to a place near Milwaukee?

Book flights to Milwaukee if you plan to visit one of these locations
Sheboygan
New Berlin
Oak Creek
Wauwatosa

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Alternative routes for Port of Spain to Milwaukee

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Top airline flying from Port of Spain to Milwaukee

Discover the top airline that operate flights from Port of Spain to Milwaukee. 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 27, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$636Average$763FlexibilityNo cancel feeOn-time69%

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