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$673+ Cheap flights from Trinidad and Tobago 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 1/26. 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 Milwaukee

Best flights from Trinidad and Tobago to Milwaukee
Discover carefully curated flight deals from Trinidad and Tobago to Milwaukee that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated December 18, 2025.

This Kiwi.com deal was found by Cheapflights users on 12/15. 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 1/2610:10 amPOS - MKE
2 stops33h 48mMultiple Airlines
Sat 2/77:48 pmMKE - POS
1 stop23h 27mMultiple Airlines
Deal found 12/15$694
This United Airlines deal was found by Cheapflights users on 12/15. 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 1/291:30 amPOS - MKE
2 stops14h 23mUnited Airlines
Thu 2/56:00 amMKE - POS
2 stops40h 23mUnited Airlines
Deal found 12/15$764
This Kiwi.com deal was found by Cheapflights users on 12/15. 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 1/2610:10 amPOS - MKE
2 stops33h 48mMultiple Airlines
Thu 2/57:13 pmMKE - POS
1 stop22h 17mMultiple Airlines
Deal found 12/15$715
This United Airlines deal was found by Cheapflights users on 12/15. 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 1/251:30 amPOS - MKE
2 stops35h 04mUnited Airlines
Thu 2/56:00 amMKE - POS
2 stops40h 23mUnited Airlines
Deal found 12/15$764
This Kiwi.com deal was found by Cheapflights users on 12/15. 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 1/3010:10 amPOS - MKE
2 stops26h 07mMultiple Airlines
Thu 2/57:13 pmMKE - POS
1 stop22h 17mMultiple Airlines
Deal found 12/15$727
This United Airlines deal was found by Cheapflights users on 12/15. 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 1/261:30 amPOS - MKE
2 stops23h 26mUnited Airlines
Thu 2/52:32 pmMKE - POS
2 stops31h 51mUnited Airlines
Deal found 12/15$764
This Kiwi.com deal was found by Cheapflights users on 12/15. 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.
Thu 1/2910:10 amPOS - MKE
2 stops34h 23mMultiple Airlines
Tue 2/36:53 pmMKE - POS
1 stop22h 37mMultiple Airlines
Deal found 12/15$746
This United Airlines deal was found by Cheapflights users on 12/15. 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 1/291:30 amPOS - MKE
2 stops12h 39mUnited Airlines
Fri 2/63:20 pmMKE - POS
2 stops31h 03mUnited Airlines
Deal found 12/15$786
This Kiwi.com deal was found by Cheapflights users on 12/15. 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 1/278:55 amPOS - MKE
2 stops35h 06mMultiple Airlines
Sat 2/77:48 pmMKE - POS
1 stop23h 27mMultiple Airlines
Deal found 12/15$765
This United Airlines deal was found by Cheapflights users on 12/15. 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 1/251:30 amPOS - MKE
2 stops12h 39mUnited Airlines
Fri 2/63:20 pmMKE - POS
2 stops31h 03mUnited Airlines
Deal found 12/15$786
This Kiwi.com deal was found by Cheapflights users on 12/15. 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 1/288:30 amPOS - MKE
1 stop11h 31mMultiple Airlines
Tue 2/36:53 pmMKE - POS
1 stop22h 37mMultiple Airlines
Deal found 12/15$783

Find flight deals from Trinidad and Tobago to Milwaukee

Keep the following information in mind while searching for Trinidad and Tobago to Milwaukee flight deals. Data was last updated December 18, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$673
(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 Trinidad and Tobago to Milwaukee-Mitchell
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Trinidad and Tobago 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 December 18, 2025.
Use the filters below to find and compare flights from Trinidad and Tobago to Milwaukee that are best for you.

Fly from

Trinidad and Tobago

Fly to

Milwaukee

Route

Depart

Return

Price

Port of SpainMilwaukee

POS - MKE

POSMKE

Port of Spain Piarco Intl

Mon 1/26

10:10 am-5:58 pm

2 stops33h 48m

Milwaukee-Mitchell

Sat 2/7

7:48 pm-9:15 pm

1 stop23h 27m

$694

Port of SpainMilwaukee

POS - MKE

POSMKE

Port of Spain Piarco Intl

Mon 1/26

10:10 am-5:58 pm

2 stops33h 48m

Milwaukee-Mitchell

Thu 2/5

7:13 pm-7:30 pm

1 stop22h 17m

$715

Port of SpainMilwaukee

POS - MKE

POSMKE

Port of Spain Piarco Intl

Fri 1/30

10:10 am-10:17 am

2 stops26h 07m

Milwaukee-Mitchell

Thu 2/5

7:13 pm-7:30 pm

1 stop22h 17m

$727

Port of SpainMilwaukee

POS - MKE

POSMKE

Port of Spain Piarco Intl

Thu 1/29

10:10 am-6:33 pm

2 stops34h 23m

Milwaukee-Mitchell

Tue 2/3

6:53 pm-7:30 pm

1 stop22h 37m

$746

Port of SpainMilwaukee

POS - MKE

POSMKE

Port of Spain Piarco Intl

Thu 1/29

1:30 am-1:53 pm

2 stops14h 23m

Milwaukee-Mitchell

Thu 2/5

6:00 am-12:23 am

2 stops40h 23m

$764

Port of SpainMilwaukee

POS - MKE

POSMKE

Port of Spain Piarco Intl

Sun 1/25

1:30 am-10:34 am

2 stops35h 04m

Milwaukee-Mitchell

Thu 2/5

6:00 am-12:23 am

2 stops40h 23m

$764

Port of SpainMilwaukee

POS - MKE

POSMKE

Port of Spain Piarco Intl

Mon 1/26

1:30 am-10:56 pm

2 stops23h 26m

Milwaukee-Mitchell

Thu 2/5

2:32 pm-12:23 am

2 stops31h 51m

$764

Port of SpainMilwaukee

POS - MKE

POSMKE

Port of Spain Piarco Intl

Tue 1/27

8:55 am-6:01 pm

2 stops35h 06m

Milwaukee-Mitchell

Sat 2/7

7:48 pm-9:15 pm

1 stop23h 27m

$765

Port of SpainMilwaukee

POS - MKE

POSMKE

Port of Spain Piarco Intl

Wed 1/28

8:30 am-6:01 pm

1 stop11h 31m

Milwaukee-Mitchell

Tue 2/3

6:53 pm-7:30 pm

1 stop22h 37m

$783

Port of SpainMilwaukee

POS - MKE

POSMKE

Port of Spain Piarco Intl

Thu 1/29

1:30 am-12:09 pm

2 stops12h 39m

Milwaukee-Mitchell

Fri 2/6

3:20 pm-12:23 am

2 stops31h 03m

$786

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/15

Showing 1-10 of 11 results
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Best time to book a flight from Trinidad and Tobago to Milwaukee

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

What is the cheapest month to book a flight from Trinidad and Tobago to Milwaukee?

Currently, December is the cheapest month in which you can book a flight from Trinidad and Tobago to Milwaukee (average of $304). Flying from Trinidad and Tobago 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 December 18, 2025.
Read through reviews of airlines operating flights from Trinidad and Tobago to Milwaukee, such as United Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
9,091 reviews

Overall

7.4

Crew

8.1

Comfort

7.3

Entertainment

7.1

Food

6.6

Boarding

7.7

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

Overall

7.4

Crew

8.1

Comfort

7.3

Entertainment

7.1

Food

6.6

Boarding

7.7

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 Milwaukee. 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 into for flights to Milwaukee from Trinidad and Tobago?

    Milwaukee-Mitchell (MKE) is the airport you will fly into if you book a flight from Trinidad and Tobago to Milwaukee. It is only a 6.4 mi journey from Milwaukee-Mitchell (MKE) to Milwaukee’s city center.

  • How long is the flight from Trinidad and Tobago to Milwaukee?

    A quick flight from Trinidad and Tobago to Milwaukee can take about 14h 23m. United Airlines provides one of the quickest options available for as low as $764. There are 2744 mi between Trinidad and Tobago and Milwaukee.

  • Can I find deals for flights from Trinidad and Tobago to Milwaukee that include hotel bookings?

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

  • How can I find direct flights from Trinidad and Tobago to Milwaukee?

    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 Milwaukee.

  • Can I find deals for business class flights from Trinidad and Tobago to Milwaukee?

    Yes. Cheapflights offers flight deals from Trinidad and Tobago 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 Trinidad and Tobago to Milwaukee?

    Currently, December is the cheapest month in which you can book a flight from Trinidad and Tobago to Milwaukee (average of $304). Flying from Trinidad and Tobago 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 Trinidad and Tobago to Milwaukee

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 Milwaukee

Discover the top airline that operate flights from Trinidad and Tobago 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 December 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$636Average$771FlexibilityNo cancel feeOn-time69%

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