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$108+ 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 4/25. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — MKE
Apr 8 — Apr 151
Tue 4/8
Tue 4/15
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 3, 2025.

Round-trip from

$271
(Mytrip)

One-way from

$108
(American Airlines)
From Caribbean Islands to Milwaukee-Mitchell
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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 3, 2025.

This Mytrip deal was found by Cheapflights users on 4/2. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/307:00 pmSJU - MKE
2 stops22h 05mSpirit Airlines
Fri 5/912:22 pmMKE - SJU
1 stop11h 32mSpirit Airlines
Deal found 4/2$271
This Delta deal was found by Cheapflights users on 4/2. 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 9/42:28 pmSJU - MKE
1 stop9h 57mDelta
Thu 9/186:00 amMKE - SJU
1 stop9h 08mDelta
Deal found 4/2$275
This American Airlines deal was found by Cheapflights users on 4/3. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/15:30 amSJU - MKE
1 stop16h 21mAmerican Airlines
Tue 5/611:23 amMKE - SJU
1 stop16h 49mAmerican Airlines
Deal found 4/3$285
This Booking.com deal was found by Cheapflights users on 4/1. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/189:21 amSJU - MKE
1 stop7h 25mMultiple Airlines
Mon 4/217:10 pmMKE - SJU
1 stop19h 50mMultiple Airlines
Deal found 4/1$311
This Frontier deal was found by Cheapflights users on 4/2. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/102:56 amSJU - MKE
1 stop13h 06mFrontier
Fri 4/183:52 pmMKE - SJU
1 stop8h 58mFrontier
Deal found 4/2$316
This United Airlines deal was found by Cheapflights users on 4/2. 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 4/301:05 amSJU - MKE
1 stop8h 12mUnited Airlines
Mon 5/53:52 pmMKE - SJU
1 stop7h 02mUnited Airlines
Deal found 4/2$325
This United Airlines deal was found by Cheapflights users on 4/2. 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.
Thu 4/241:51 pmMBJ - MKE
1 stop29h 16mUnited Airlines
Sun 4/272:22 pmMKE - MBJ
1 stop22h 27mUnited Airlines
Deal found 4/2$452
This Delta deal was found by Cheapflights users on 4/2. 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 4/244:56 pmMBJ - MKE
1 stop6h 58mDelta
Sat 4/265:45 amMKE - MBJ
1 stop9h 46mDelta
Deal found 4/2$475
This United Airlines deal was found by Cheapflights users on 4/2. 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.
Sat 4/261:50 pmPUJ - MKE
1 stop9h 25mUnited Airlines
Sun 5/410:15 amMKE - PUJ
1 stop27h 50mUnited Airlines
Deal found 4/2$487
This Delta deal was found by Cheapflights users on 4/2. 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.
Sat 4/262:40 pmPUJ - MKE
1 stop10h 14mDelta
Sun 5/45:45 amMKE - PUJ
1 stop7h 45mDelta
Deal found 4/2$542
This American Airlines deal was found by Cheapflights users on 4/2. 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 5/2910:10 amMBJ - MKE
2 stops11h 00mAmerican Airlines
Tue 9/25:06 amMKE - MBJ
1 stop7h 36mAmerican Airlines
Deal found 4/2$559
This Mytrip deal was found by Cheapflights users on 4/2. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/2611:50 amPUJ - MKE
2 stops29h 15mSpirit Airlines
Sun 5/45:00 pmMKE - PUJ
3 stops41h 44mSpirit Airlines
Deal found 4/2$601

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 3, 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

Wed 4/30

7:00 pm-4:05 pm

2 stops22h 05m

Milwaukee-Mitchell

Fri 5/9

12:22 pm-12:54 am

1 stop11h 32m

$271

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Thu 5/1

5:30 am-8:51 pm

1 stop16h 21m

Milwaukee-Mitchell

Tue 5/6

11:23 am-5:12 am

1 stop16h 49m

$285

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Fri 4/18

9:21 am-3:46 pm

1 stop7h 25m

Milwaukee-Mitchell

Mon 4/21

7:10 pm-4:00 pm

1 stop19h 50m

$311

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Thu 4/10

2:56 am-3:02 pm

1 stop13h 06m

Milwaukee-Mitchell

Fri 4/18

3:52 pm-1:50 am

1 stop8h 58m

$316

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Wed 4/30

1:05 am-8:17 am

1 stop8h 12m

Milwaukee-Mitchell

Mon 5/5

3:52 pm-11:54 pm

1 stop7h 02m

$325

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Wed 4/30

5:11 pm-11:54 pm

1 stop7h 43m

Milwaukee-Mitchell

Fri 5/9

2:59 pm-10:47 pm

1 stop6h 48m

$345

Montego BayMilwaukee

MBJ - MKE

MBJMKE

Montego Bay Sangster Intl

Thu 4/24

1:51 pm-7:07 pm

1 stop29h 16m

Milwaukee-Mitchell

Sun 4/27

2:22 pm-12:49 pm

1 stop22h 27m

$452

Montego BayMilwaukee

MBJ - MKE

MBJMKE

Montego Bay Sangster Intl

Thu 4/24

4:56 pm-11:54 pm

1 stop6h 58m

Milwaukee-Mitchell

Sat 4/26

5:45 am-3:31 pm

1 stop9h 46m

$475

Punta CanaMilwaukee

PUJ - MKE

PUJMKE

Punta Cana

Sat 4/26

1:50 pm-10:15 pm

1 stop9h 25m

Milwaukee-Mitchell

Sun 5/4

10:15 am-3:05 pm

1 stop27h 50m

$487

Punta CanaMilwaukee

PUJ - MKE

PUJMKE

Punta Cana

Sat 4/26

2:40 pm-11:54 pm

1 stop10h 14m

Milwaukee-Mitchell

Sun 5/4

5:45 am-2:30 pm

1 stop7h 45m

$542

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/2

Showing 1-10 of 33 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 3, 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 3, 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
9,827 reviews

Entertainment

7.1

Crew

8.5

Overall

8.0

Food

7.1

Boarding

8.2

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Alaska Airlines
8.0
Very good
9,827 reviews
Alaska Airlines
8.0
Very good
9,827 reviews

Entertainment

7.1

Crew

8.5

Overall

8.0

Food

7.1

Boarding

8.2

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Southwest
8.0
Very good
4,274 reviews
Alaska Airlines
8.0
Very good
9,827 reviews

Entertainment

7.1

Crew

8.5

Overall

8.0

Food

7.1

Boarding

8.2

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Delta
8.0
Very good
7,897 reviews
Alaska Airlines
8.0
Very good
9,827 reviews

Entertainment

7.1

Crew

8.5

Overall

8.0

Food

7.1

Boarding

8.2

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
LATAM Airlines
7.5
Good
1,754 reviews
Alaska Airlines
8.0
Very good
9,827 reviews

Entertainment

7.1

Crew

8.5

Overall

8.0

Food

7.1

Boarding

8.2

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
United Airlines
7.4
Good
8,619 reviews
Alaska Airlines
8.0
Very good
9,827 reviews

Entertainment

7.1

Crew

8.5

Overall

8.0

Food

7.1

Boarding

8.2

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

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?

    $108 is the cheapest one-way deal found within the past few days, from American Airlines. You may also be able to find cheap deals on United Airlines and Spirit Airlines, with prices starting from $118 and $131, 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 Montego Bay Sangster Intl - Milwaukee-Mitchell or Christiansted Henry Rohlsen - 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

Browse thousands of different options on Cheapflights for your next trip

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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 6 airlines flying from Caribbean Islands to Milwaukee

Discover the top 6 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 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$182Average$345FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$215Average$419FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$265Average$396FlexibilityNo cancel feeOn-time71%
DeltaCheapest$275Average$398FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$378Average$481FlexibilityNo cancel feeOn-time63%
JetBlueCheapest$397Average$457FlexibilityNo cancel feeOn-time62%

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