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Caribbean Islands

$108+ Cheap flights from Milwaukee (MKE) to Caribbean Islands

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 7/15. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SJU
Apr 29 — May 61
Tue 4/29
Tue 5/6
1 adult, Economy
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Cheap flight deals from Milwaukee to Caribbean Islands

Keep the following information in mind while searching for Milwaukee to Caribbean Islands flight deals. Data was last updated April 24, 2025.

Round-trip from

$292
(United Airlines)

One-way from

$108
(Delta)

Popular in

December

Cheapest in

September

Average price

$373
From Milwaukee-Mitchell to Caribbean Islands
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One-way flight from Milwaukee-Mitchell to Caribbean Islands
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Highest demand for flights based on searches. 9% potential increase in price ($49 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($17 potential savings vs. average RT price).
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Average for round-trip flights in April 2025
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Find flight deals from Milwaukee to Caribbean Islands

Cheapest flights from Milwaukee to Caribbean Islands
Explore the most affordable flight options available from Milwaukee to Caribbean Islands. 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 4/22. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/167:00 amMKE - SJU
1 stop8h 18mDelta
Tue 9/235:19 pmSJU - MKE
1 stop7h 06mDelta
Deal found 4/22$215
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.
Wed 5/73:52 pmMKE - SJU
1 stop7h 02mUnited Airlines
Tue 5/131:05 amSJU - MKE
1 stop8h 12mUnited Airlines
Deal found 4/23$292
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/1912:22 pmMKE - SJU
1 stop11h 32mSpirit Airlines
Fri 6/61:59 amSJU - MKE
1 stop10h 28mSpirit Airlines
Deal found 4/22$311
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/1710:05 amMKE - SJU
2 stops9h 28mAmerican Airlines
Tue 5/205:25 amSJU - MKE
1 stop16h 45mAmerican Airlines
Deal found 4/22$312
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.
Tue 8/196:00 amMKE - PLS
1 stop5h 45mDelta
Tue 8/262:05 pmPLS - MKE
1 stop7h 08mDelta
Deal found 4/23$360
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.
Tue 8/195:43 pmMKE - PLS
2 stops17h 22mAmerican Airlines
Tue 8/2611:20 amPLS - MKE
1 stop7h 02mAmerican Airlines
Deal found 4/23$364
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/69:15 amMKE - STT
2 stops23h 42mSpirit Airlines
Sun 6/81:21 pmSTT - MKE
1 stop23h 06mSpirit Airlines
Deal found 4/22$373
This Kiwi.com deal was found by Cheapflights users on 4/21. 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 4/2912:32 pmMKE - PUJ
1 stop24h 41mSpirit Airlines
Sat 5/33:18 pmPUJ - MKE
1 stop25h 47mSpirit Airlines
Deal found 4/21$378
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.
Tue 9/94:41 pmMKE - AUA
2 stops19h 39mAmerican Airlines
Tue 9/165:25 pmAUA - MKE
2 stops17h 09mAmerican Airlines
Deal found 4/23$406
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/1910:35 amMKE - SJU
2 stops13h 19mMultiple Airlines
Sat 6/74:20 pmSJU - MKE
1 stop26h 09mMultiple Airlines
Deal found 4/23$412
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.
Sat 6/74:19 pmMKE - STX
2 stops21h 35mAmerican Airlines
Thu 6/125:20 pmSTX - MKE
2 stops20h 27mAmerican Airlines
Deal found 4/23$419
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/148:51 pmMKE - MBJ
2 stops14h 50mSpirit Airlines
Sat 10/2512:11 pmMBJ - MKE
1 stop7h 45mSpirit Airlines
Deal found 4/23$431

Cheapflights Fare Finder

Customize your flight search to find flights from Milwaukee to Caribbean Islands 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 Milwaukee to Caribbean Islands that are best for you.

Fly from

Milwaukee

Fly to

Caribbean Islands

Route

Depart

Return

Price

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Wed 5/7

3:52 pm-11:54 pm

1 stop7h 02m

San Juan Luis Munoz Marin Intl

Tue 5/13

1:05 am-8:17 am

1 stop8h 12m

$292

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Sun 5/25

7:07 am-3:00 pm

1 stop6h 53m

San Juan Luis Munoz Marin Intl

Mon 6/2

7:15 am-11:58 pm

1 stop17h 43m

$312

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Thu 5/8

12:22 pm-12:54 am

1 stop11h 32m

San Juan Luis Munoz Marin Intl

Wed 5/14

1:59 am-11:27 am

1 stop10h 28m

$313

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Sun 5/25

2:59 pm-10:47 pm

1 stop6h 48m

San Juan Luis Munoz Marin Intl

Thu 5/29

6:15 am-3:51 pm

1 stop10h 36m

$315

MilwaukeeProvidenciales

MKE - PLS

MKEPLS

Milwaukee-Mitchell

Tue 8/19

6:00 am-12:45 pm

1 stop5h 45m

Providenciales

Tue 8/26

2:05 pm-8:13 pm

1 stop7h 08m

$360

MilwaukeeProvidenciales

MKE - PLS

MKEPLS

Milwaukee-Mitchell

Tue 8/19

5:43 pm-12:05 pm

2 stops17h 22m

Providenciales

Tue 8/26

11:20 am-5:22 pm

1 stop7h 02m

$364

MilwaukeeSaint Thomas Island

MKE - STT

MKESTT

Milwaukee-Mitchell

Fri 6/6

9:15 am-9:57 am

2 stops23h 42m

Saint Thomas Island Cyril E King

Sun 6/8

1:21 pm-11:27 am

1 stop23h 06m

$373

MilwaukeeOranjestad

MKE - AUA

MKEAUA

Milwaukee-Mitchell

Tue 9/9

5:20 am-3:30 pm

1 stop9h 10m

Oranjestad Reina Beatrix

Tue 9/16

4:45 pm-9:53 am

2 stops18h 08m

$406

MilwaukeeChristiansted

MKE - STX

MKESTX

Milwaukee-Mitchell

Sat 6/7

4:19 pm-2:54 pm

2 stops21h 35m

Christiansted Henry Rohlsen

Thu 6/12

5:20 pm-12:47 pm

2 stops20h 27m

$419

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Sun 6/1

6:10 pm-11:31 am

3 stops40h 21m

San Juan Luis Munoz Marin Intl

Thu 6/5

1:59 am-11:27 am

1 stop10h 28m

$426

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/23

Showing 1-10 of 43 results
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Best time to book a flight from Milwaukee to Caribbean Islands

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

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

Currently, September is the cheapest month in which you can book a flight from Milwaukee to Caribbean Islands (average of $254). Flying from Milwaukee to Caribbean Islands in December is currently the most expensive (average of $336). 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 MKE to EPX?

Find hourly flight availability from Milwaukee to Caribbean Islands. 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.

When flying from Milwaukee to Caribbean Islands, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Rainfall in Caribbean Islands by month

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

In terms of precipitation, rainfall in Caribbean Islands ranges from 2.2 - 6.1 inches per month. November is typically the wettest month, when rainfall can reach 6.1 in. February is typically the driest time to visit Caribbean Islands when rainfall is around 2.2 in.

Temperature in Caribbean Islands by month

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

If weather is an important factor for your trip to Caribbean Islands, use this chart to help with planning. For those seeking warmer temperatures, June is the ideal time of year to visit, when temperatures reach an average of 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 77.0 F).

Reviews of airlines servicing Caribbean Islands

Get insights into the airlines that provide service to Caribbean Islands. 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 Caribbean Islands. Reviews last updated April 24, 2025.
Read through reviews of airlines operating flights from Milwaukee to Caribbean Islands, such as Alaska Airlines, Southwest and Delta. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
9,918 reviews

Comfort

7.9

Entertainment

7.1

Overall

8.0

Boarding

8.2

Food

7.1

Crew

8.5

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

Comfort

7.9

Entertainment

7.1

Overall

8.0

Boarding

8.2

Food

7.1

Crew

8.5

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
4,287 reviews
Alaska Airlines
8.0
Very good
9,918 reviews

Comfort

7.9

Entertainment

7.1

Overall

8.0

Boarding

8.2

Food

7.1

Crew

8.5

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

Comfort

7.9

Entertainment

7.1

Overall

8.0

Boarding

8.2

Food

7.1

Crew

8.5

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
1,767 reviews
Alaska Airlines
8.0
Very good
9,918 reviews

Comfort

7.9

Entertainment

7.1

Overall

8.0

Boarding

8.2

Food

7.1

Crew

8.5

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

Comfort

7.9

Entertainment

7.1

Overall

8.0

Boarding

8.2

Food

7.1

Crew

8.5

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 Milwaukee to Caribbean Islands. 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 from for flights from Milwaukee to Caribbean Islands?

    Milwaukee-Mitchell (MKE) is the airport you will fly out of if you book a flight from Milwaukee to Caribbean Islands. It is only a 6.4 mi journey to Milwaukee-Mitchell (MKE) from Milwaukee’s city center.

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

    For one-way options, check prices for Delta. According to our data, you can fly for as low as $108. Users have also found prices from $144 and $189 on Spirit Airlines and American Airlines, respectively.

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

    When deciding which route to take from Milwaukee to Caribbean Islands consider Milwaukee-Mitchell - San Juan Luis Munoz Marin Intl, Milwaukee-Mitchell - Punta Cana or Milwaukee-Mitchell - Oranjestad Reina Beatrix as they are the most popular.

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

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

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

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

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

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

    Currently, September is the cheapest month in which you can book a flight from Milwaukee to Caribbean Islands (average of $254). Flying from Milwaukee to Caribbean Islands in December is currently the most expensive (average of $336). 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

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Alternative routes for Milwaukee to Caribbean Islands

See prices for flight routes from nearby airports that may be better suited for you.
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Top 8 airlines flying from Milwaukee to Caribbean Islands

Discover the top 8 airlines that operate flights from Milwaukee to Caribbean Islands. 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
FrontierCheapest$129Average$245FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$195Average$451FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$248Average$463FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$258Average$565FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$266Average$711FlexibilityNo cancel feeOn-time71%
DeltaCheapest$289Average$541FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$375Average$765FlexibilityNo cancel feeOn-time63%
Sun Country AirCheapest$495Average$646FlexibilityNo cancel feeOn-time83%

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