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$84+ Cheap flights from Caribbean Islands to Milwaukee (MKE)

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 1/31. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — MKE
Dec 2 — Dec 91
Tue 12/2
Tue 12/9
1 adult, Economy
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Find flight deals from Caribbean Islands to Milwaukee

Cheapest flights from Caribbean Islands to Milwaukee
Explore the most affordable flight options available from Caribbean Islands to Milwaukee. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 2, 2025.

This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/54:40 pmSJU - MKE
1 stop7h 05mSouthwest
Mon 12/811:05 amMKE - SJU
1 stop9h 00mSouthwest
Deal found 11/1$274
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/253:44 pmSJU - MKE
1 stop6h 51mDelta
Tue 1/67:02 amMKE - SJU
1 stop7h 50mDelta
Deal found 11/2$300
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.
Thu 12/43:41 pmSJU - MKE
1 stop10h 20mAmerican Airlines
Wed 12/106:01 amMKE - SJU
2 stops9h 02mAmerican Airlines
Deal found 11/2$308
This Cheapflightsfares deal was found by Cheapflights users on 10/31. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/2511:38 amSJU - MKE
1 stop9h 42mSpirit Airlines
Mon 1/58:15 pmMKE - SJU
1 stop12h 18mSpirit Airlines
Deal found 10/31$326
This CheapOair deal was found by Cheapflights users on 10/31. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/2511:38 amSJU - MKE
1 stop9h 42mSpirit Airlines
Tue 1/68:15 pmMKE - SJU
1 stop12h 18mSpirit Airlines
Deal found 10/31$343
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/225:09 pmSJU - MKE
1 stop27h 17mMultiple Airlines
Sun 1/48:15 pmMKE - SJU
1 stop12h 18mMultiple Airlines
Deal found 11/2$345
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/243:55 amSJU - MKE
1 stop17h 25mMultiple Airlines
Tue 1/68:15 pmMKE - SJU
1 stop28h 35mMultiple Airlines
Deal found 11/2$351
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/223:55 amSJU - MKE
1 stop16h 31mMultiple Airlines
Sat 1/38:15 pmMKE - SJU
1 stop16h 05mMultiple Airlines
Deal found 11/1$355
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/257:15 amSJU - MKE
1 stop16h 16mAmerican Airlines
Tue 12/26:06 amMKE - SJU
2 stops9h 46mAmerican Airlines
Deal found 11/1$360
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.
Wed 12/32:05 amSJU - MKE
1 stop10h 39mUnited Airlines
Wed 12/108:40 amMKE - SJU
2 stops11h 42mUnited Airlines
Deal found 11/2$364
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/263:59 amSJU - MKE
1 stop9h 41mMultiple Airlines
Fri 12/56:09 pmMKE - SJU
1 stop30h 41mMultiple Airlines
Deal found 11/2$365
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/83:49 pmSTT - MKE
1 stop10h 06mDelta
Sun 11/165:45 amMKE - STT
1 stop6h 55mDelta
Deal found 11/1$683

Cheap flight deals from Caribbean Islands to Milwaukee

Keep the following information in mind while searching for Caribbean Islands to Milwaukee flight deals. Data was last updated November 2, 2025.

Round-trip from

$138
(Frontier)

One-way from

$84
(Priceline)
From Caribbean Islands to Milwaukee-Mitchell
Search Deals
One-way flight from Caribbean Islands to Milwaukee-Mitchell
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Caribbean Islands 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 November 2, 2025.
Use the filters below to find and compare flights from Caribbean Islands to Milwaukee that are best for you.

Fly from

Caribbean Islands

Fly to

Milwaukee

Route

Depart

Return

Price

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Thu 2/19

11:05 am-6:45 pm

1 stop9h 40m

Milwaukee-Mitchell

Mon 2/23

7:40 pm-9:55 am

1 stop12h 15m

$153

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Fri 12/5

4:40 pm-9:45 pm

1 stop7h 05m

Milwaukee-Mitchell

Mon 12/8

11:05 am-10:05 pm

1 stop9h 00m

$274

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Thu 12/25

3:44 pm-8:35 pm

1 stop6h 51m

Milwaukee-Mitchell

Tue 1/6

7:02 am-4:52 pm

1 stop7h 50m

$300

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Thu 12/4

2:36 pm-12:01 am

2 stops11h 25m

Milwaukee-Mitchell

Wed 12/10

6:01 am-10:09 pm

2 stops14h 08m

$308

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Wed 12/24

6:00 am-5:49 pm

1 stop13h 49m

Milwaukee-Mitchell

Sat 1/3

11:19 am-5:00 am

1 stop15h 41m

$308

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Thu 12/25

11:38 am-7:20 pm

1 stop9h 42m

Milwaukee-Mitchell

Mon 1/5

8:15 pm-10:33 am

1 stop12h 18m

$326

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Tue 11/25

7:15 am-9:31 pm

1 stop16h 16m

Milwaukee-Mitchell

Tue 12/2

12:00 pm-12:44 am

2 stops10h 44m

$360

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Wed 1/28

2:05 am-3:43 pm

2 stops15h 38m

Milwaukee-Mitchell

Mon 2/2

8:33 am-12:36 am

2 stops14h 03m

$364

Montego BayMilwaukee

MBJ - MKE

MBJMKE

Montego Bay Sangster Intl

Fri 3/6

2:48 pm-10:43 pm

1 stop8h 55m

Milwaukee-Mitchell

Tue 3/10

5:00 am-12:46 pm

1 stop7h 46m

$503

Punta CanaMilwaukee

PUJ - MKE

PUJMKE

Punta Cana

Mon 3/9

3:25 pm-10:30 am

1 stop20h 05m

Milwaukee-Mitchell

Wed 3/11

1:25 pm-2:19 pm

1 stop23h 54m

$598

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/2

Showing 1-10 of 49 results
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Best time to book a flight from Caribbean Islands to Milwaukee

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

What is the cheapest month to book a flight from Caribbean Islands to Milwaukee?

Currently, September is the cheapest month in which you can book a flight from Caribbean Islands to Milwaukee (average of $113). Flying from Caribbean Islands to Milwaukee in June is currently the most expensive (average of $184). 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.

What is the cheapest time of day to fly from EPX to MKE?

Find hourly flight availability from Caribbean Islands to Milwaukee. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated November 2, 2025.

It’s optimal to fly from Caribbean Islands to Milwaukee in the morning. By choosing this option you can save up to 23% on the cost of your flight, compared to a flight at noon.

What is the cheapest day to fly from Caribbean Islands to Milwaukee?

Use this chart to determine the cheapest time to fly round-trip from Caribbean Islands to Milwaukee. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Caribbean Islands to Milwaukee flight should consider departing on Saturday afternoons when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

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 November 2, 2025.
Read through reviews of airlines operating flights from Caribbean Islands to Milwaukee, such as Delta, United Airlines, and American Airlines. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
8,001 reviews

Boarding

8.2

Comfort

7.9

Crew

8.5

Entertainment

7.9

Food

7.3

Overall

7.9

Reviews

1 / 20
8.0
Excellent

Lane,Nov 2025

MEM - ATL

The crew was very friendly, but they only came around and offered the better Delta Comfort snacks one time. I thought they would come around more frequently on a 5 hour flight. They did do two beverage services though, which was nice.
Delta
7.9
Good
8,001 reviews
Delta
7.9
Good
8,001 reviews

Boarding

8.2

Comfort

7.9

Crew

8.5

Entertainment

7.9

Food

7.3

Overall

7.9

Reviews

1 / 20
8.0
Excellent

Lane,Nov 2025

MEM - ATL

The crew was very friendly, but they only came around and offered the better Delta Comfort snacks one time. I thought they would come around more frequently on a 5 hour flight. They did do two beverage services though, which was nice.
United Airlines
7.4
Good
8,997 reviews
Delta
7.9
Good
8,001 reviews

Boarding

8.2

Comfort

7.9

Crew

8.5

Entertainment

7.9

Food

7.3

Overall

7.9

Reviews

1 / 20
8.0
Excellent

Lane,Nov 2025

MEM - ATL

The crew was very friendly, but they only came around and offered the better Delta Comfort snacks one time. I thought they would come around more frequently on a 5 hour flight. They did do two beverage services though, which was nice.
American Airlines
7.2
Good
11,034 reviews
Delta
7.9
Good
8,001 reviews

Boarding

8.2

Comfort

7.9

Crew

8.5

Entertainment

7.9

Food

7.3

Overall

7.9

Reviews

1 / 20
8.0
Excellent

Lane,Nov 2025

MEM - ATL

The crew was very friendly, but they only came around and offered the better Delta Comfort snacks one time. I thought they would come around more frequently on a 5 hour flight. They did do two beverage services though, which was nice.

Related info for your journey

Find useful and relevant information for your journey from Caribbean Islands 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 Caribbean Islands?

    If you book a flight to Milwaukee from Caribbean Islands, you will be flying to Milwaukee-Mitchell, which is the city’s only airport. Milwaukee-Mitchell (MKE) is located 6.4 mi from the center of Milwaukee.

  • How long is the flight from Caribbean Islands to Milwaukee?

    A quick flight from Caribbean Islands to Milwaukee can take about 6h 51m. Frontier provides one of the quickest options available for as low as $300. Airlines will cover a distance of 2120 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines to fly from Caribbean Islands to Milwaukee one-way?

    $118 is the cheapest one-way deal found within the past few days, from Southwest. You may also be able to find cheap deals on United Airlines and Delta, with prices starting from $118 and $118, respectively.

  • What are the most popular routes from Caribbean Islands to Milwaukee?

    The most popular route from Caribbean Islands to Milwaukee is San Juan Luis Munoz Marin Intl - Milwaukee-Mitchell. You may also consider Port of Spain Piarco Intl - Milwaukee-Mitchell or Culebra - Milwaukee-Mitchell.

  • Can I find deals for flights from Caribbean Islands to Milwaukee that include hotel bookings?

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

  • How can I find direct flights from Caribbean Islands to Milwaukee?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Caribbean Islands to Milwaukee.

  • Can I find deals for business class flights from Caribbean Islands to Milwaukee?

    Yes. Cheapflights offers flight deals from Caribbean Islands 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 Caribbean Islands to Milwaukee?

    Currently, September is the cheapest month in which you can book a flight from Caribbean Islands to Milwaukee (average of $113). Flying from Caribbean Islands to Milwaukee in June is currently the most expensive (average of $184). 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 Caribbean Islands to Milwaukee

See prices for flight routes from nearby airports that may be better suited for you.
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Top 4 airlines flying from Caribbean Islands to Milwaukee

Discover the top 4 airlines that operate flights from Caribbean Islands 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 November 2, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$215Average$399FlexibilityNo cancel feeOn-time69%
DeltaCheapest$215Average$445FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$235Average$437FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$305Average$485FlexibilityNo cancel feeOn-time63%

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