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$141+ 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 5/1. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — MKE
Apr 29 — May 61
Tue 4/29
Tue 5/6
1 adult, Economy
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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 April 24, 2025.

Round-trip from

$256
(Delta)

One-way from

$141
(eDestinos)
From Caribbean Islands to Milwaukee-Mitchell
Search Deals
One-way flight from Caribbean Islands to Milwaukee-Mitchell
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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 April 24, 2025.

This Delta deal was found by Cheapflights users on 4/23. 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 9/412:56 pmSJU - MKE
1 stop11h 29mDelta
Thu 9/186:00 amMKE - SJU
1 stop9h 08mDelta
Deal found 4/23$256
This eDestinos deal was found by Cheapflights users on 4/23. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/81:59 amSJU - MKE
2 stops8h 41mSpirit Airlines
Mon 5/1210:35 amMKE - SJU
2 stops13h 19mSpirit Airlines
Deal found 4/23$275
This American Airlines deal was found by Cheapflights users on 4/23. 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 9/48:30 amSJU - MKE
2 stops15h 59mAmerican Airlines
Thu 9/184:41 pmMKE - SJU
2 stops17h 34mAmerican Airlines
Deal found 4/23$299
This United Airlines deal was found by Cheapflights users on 4/23. 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 5/201:05 amSJU - MKE
1 stop8h 12mUnited Airlines
Tue 5/275:15 amMKE - SJU
1 stop8h 29mUnited Airlines
Deal found 4/23$355
This Trip.com deal was found by Cheapflights users on 4/22. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/86:00 amSJU - MKE
1 stop8h 53mMultiple Airlines
Mon 5/1212:22 pmMKE - SJU
1 stop11h 32mMultiple Airlines
Deal found 4/22$390
This Southwest deal was found by Cheapflights users on 4/23. 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.
Thu 7/245:30 pmSJU - MKE
1 stop6h 55mSouthwest
Tue 7/295:00 amMKE - SJU
2 stops10h 00mSouthwest
Deal found 4/23$475
This Mytrip deal was found by Cheapflights users on 4/23. 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.
Wed 5/143:22 pmPUJ - MKE
2 stops21h 05mSpirit Airlines
Wed 5/2112:22 pmMKE - PUJ
2 stops23h 33mSpirit Airlines
Deal found 4/23$525
This Delta deal was found by Cheapflights users on 4/23. 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.
Wed 5/141:05 pmPUJ - MKE
1 stop8h 30mDelta
Wed 5/215:40 amMKE - PUJ
1 stop8h 05mDelta
Deal found 4/23$536
This Alaska Airlines deal was found by Cheapflights users on 4/23. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/2412:59 amSJU - MKE
2 stops24h 00mAlaska Airlines
Sat 8/26:30 amMKE - SJU
2 stops30h 48mAlaska Airlines
Deal found 4/23$1,842

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 April 24, 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 9/4

12:56 pm-11:25 pm

1 stop11h 29m

Milwaukee-Mitchell

Thu 9/18

6:00 am-4:08 pm

1 stop9h 08m

$256

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Thu 5/8

1:59 am-9:40 am

2 stops8h 41m

Milwaukee-Mitchell

Mon 5/12

10:35 am-12:54 am

2 stops13h 19m

$275

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Thu 9/4

8:30 am-11:29 pm

2 stops15h 59m

Milwaukee-Mitchell

Thu 9/18

4:41 pm-11:15 am

2 stops17h 34m

$299

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Tue 5/20

1:05 am-8:17 am

1 stop8h 12m

Milwaukee-Mitchell

Tue 5/27

5:15 am-2:44 pm

1 stop8h 29m

$355

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Thu 5/8

6:00 am-1:53 pm

1 stop8h 53m

Milwaukee-Mitchell

Mon 5/12

12:22 pm-12:54 am

1 stop11h 32m

$390

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Thu 7/24

5:30 pm-11:25 pm

1 stop6h 55m

Milwaukee-Mitchell

Tue 7/29

5:00 am-4:00 pm

2 stops10h 00m

$475

Punta CanaMilwaukee

PUJ - MKE

PUJMKE

Punta Cana

Wed 5/14

3:22 pm-11:27 am

2 stops21h 05m

Milwaukee-Mitchell

Wed 5/21

12:22 pm-12:55 pm

2 stops23h 33m

$525

Punta CanaMilwaukee

PUJ - MKE

PUJMKE

Punta Cana

Wed 5/14

1:05 pm-8:35 pm

1 stop8h 30m

Milwaukee-Mitchell

Wed 5/21

5:40 am-2:45 pm

1 stop8h 05m

$536

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Thu 7/24

12:59 am-11:59 pm

2 stops24h 00m

Milwaukee-Mitchell

Sat 8/2

6:30 am-2:18 pm

2 stops30h 48m

$1,842

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Thu 5/1

9:25 am-4:05 pm

1 stop7h 40m

$141

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/23

Showing 1-10 of 27 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, February is the cheapest month in which you can book a flight from Caribbean Islands to Milwaukee (average of $280). Flying from Caribbean Islands to Milwaukee in June is currently the most expensive (average of $376). 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 April 24, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Caribbean Islands to Milwaukee as you normally would.

Rainfall in Milwaukee by month

Plan your trip to Milwaukee by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Milwaukee ranges from 1.4 - 4.0 inches per month. June is typically the wettest month, when rainfall can reach 4.0 in. January is typically the driest time to visit Milwaukee when rainfall is around 1.4 in.

Temperature in Milwaukee by month

Plan your trip to Milwaukee by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Milwaukee, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 21.2 F).

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 April 24, 2025.
Read through reviews of airlines operating flights from Caribbean Islands to Milwaukee, such as Alaska Airlines, Southwest and Delta. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
9,918 reviews

Boarding

8.2

Overall

8.0

Crew

8.5

Entertainment

7.1

Comfort

7.9

Food

7.1

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Alaska Airlines
8.0
Very good
9,918 reviews
Alaska Airlines
8.0
Very good
9,918 reviews

Boarding

8.2

Overall

8.0

Crew

8.5

Entertainment

7.1

Comfort

7.9

Food

7.1

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Southwest
8.0
Very good
4,286 reviews
Alaska Airlines
8.0
Very good
9,918 reviews

Boarding

8.2

Overall

8.0

Crew

8.5

Entertainment

7.1

Comfort

7.9

Food

7.1

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Delta
8.0
Very good
7,920 reviews
Alaska Airlines
8.0
Very good
9,918 reviews

Boarding

8.2

Overall

8.0

Crew

8.5

Entertainment

7.1

Comfort

7.9

Food

7.1

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
LATAM Airlines
7.5
Good
1,765 reviews
Alaska Airlines
8.0
Very good
9,918 reviews

Boarding

8.2

Overall

8.0

Crew

8.5

Entertainment

7.1

Comfort

7.9

Food

7.1

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
United Airlines
7.4
Good
8,685 reviews
Alaska Airlines
8.0
Very good
9,918 reviews

Boarding

8.2

Overall

8.0

Crew

8.5

Entertainment

7.1

Comfort

7.9

Food

7.1

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >

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.

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

    $141 is the cheapest one-way deal found within the past few days, from Spirit Airlines. You may also be able to find cheap deals on Delta and American Airlines, with prices starting from $158 and $189, 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 Culebra - Milwaukee-Mitchell or Montego Bay Sangster Intl - 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, February is the cheapest month in which you can book a flight from Caribbean Islands to Milwaukee (average of $280). Flying from Caribbean Islands to Milwaukee in June is currently the most expensive (average of $376). 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 Caribbean Islands?

Book flights to Caribbean Islands if you plan to visit one of these locations
Mequon
Pewaukee
Sheboygan
Oak Creek
Wauwatosa

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Alternative routes for Caribbean Islands to Milwaukee

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Top 5 airlines flying from Caribbean Islands to Milwaukee

Discover the top 5 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 April 24, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$182Average$345FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$215Average$419FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$265Average$381FlexibilityNo cancel feeOn-time71%
DeltaCheapest$275Average$395FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$323Average$481FlexibilityNo cancel feeOn-time63%

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