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Caribbean

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

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 9/16. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SJU
Apr 22 — Apr 291
Tue 4/22
Tue 4/29
1 adult, Economy
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Cheap flight deals from Milwaukee to Caribbean

Keep the following information in mind while searching for Milwaukee to Caribbean flight deals. Data was last updated April 17, 2025.

Round-trip from

$215
(American Airlines)

One-way from

$108
(American Airlines)

Popular in

December

Cheapest in

September

Average price

$370
From Milwaukee-Mitchell to Caribbean
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One-way flight from Milwaukee-Mitchell to Caribbean
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Highest demand for flights based on searches. 9% potential increase in price ($47 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% 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

Cheapest flights from Milwaukee to Caribbean
Explore the most affordable flight options available from Milwaukee to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 17, 2025.

This American Airlines deal was found by Cheapflights users on 4/16. 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.
Sun 9/74:41 pmMKE - SJU
2 stops17h 34mAmerican Airlines
Sat 9/133:55 pmSJU - MKE
1 stop8h 34mAmerican Airlines
Deal found 4/16$215
This Delta deal was found by Cheapflights users on 4/16. 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.
Sun 5/2510:00 amMKE - SJU
1 stop8h 48mDelta
Sat 5/316:15 amSJU - MKE
1 stop8h 39mDelta
Deal found 4/16$297
This CheapOair deal was found by Cheapflights users on 4/16. 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 5/199:15 amMKE - SJU
1 stop12h 23mSpirit Airlines
Fri 6/61:59 amSJU - MKE
1 stop10h 28mSpirit Airlines
Deal found 4/16$298
This United Airlines deal was found by Cheapflights users on 4/17. 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 9/167:00 amMKE - SJU
1 stop6h 44mUnited Airlines
Mon 9/221:05 amSJU - MKE
2 stops11h 25mUnited Airlines
Deal found 4/17$305
This Mytrip deal was found by Cheapflights users on 4/16. 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 5/1712:22 pmMKE - PUJ
1 stop22h 25mSpirit Airlines
Sat 5/2412:42 pmPUJ - MKE
1 stop23h 45mSpirit Airlines
Deal found 4/16$333
This Mytrip deal was found by Cheapflights users on 4/16. 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.
Sun 5/2512:22 pmMKE - STT
1 stop24h 14mSpirit Airlines
Thu 5/294:35 pmSTT - MKE
1 stop19h 52mSpirit Airlines
Deal found 4/16$339
This American Airlines deal was found by Cheapflights users on 4/17. 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 8/236:53 pmMKE - PLS
1 stop14h 27mAmerican Airlines
Sat 8/3011:20 amPLS - MKE
1 stop13h 10mAmerican Airlines
Deal found 4/17$385
This Delta deal was found by Cheapflights users on 4/16. 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.
Mon 8/257:00 amMKE - NAS
1 stop5h 41mDelta
Fri 8/293:06 pmNAS - MKE
1 stop9h 19mDelta
Deal found 4/16$399
This Southwest deal was found by Cheapflights users on 4/16. 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.
Sat 5/175:25 amMKE - SJU
2 stops8h 40mSouthwest
Sat 5/247:05 amSJU - MKE
1 stop9h 40mSouthwest
Deal found 4/16$400
This American Airlines deal was found by Cheapflights users on 4/16. 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.
Mon 8/257:25 amMKE - NAS
2 stops8h 10mAmerican Airlines
Fri 8/2911:12 amNAS - MKE
1 stop7h 10mAmerican Airlines
Deal found 4/16$403
This Mytrip deal was found by Cheapflights users on 4/16. 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 6/712:22 pmMKE - SJU
1 stop11h 32mMultiple Airlines
Wed 6/112:54 pmSJU - MKE
2 stops27h 23mMultiple Airlines
Deal found 4/16$408
This Mytrip deal was found by Cheapflights users on 4/16. 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.
Sun 5/2512:22 pmMKE - MBJ
2 stops22h 40mSpirit Airlines
Thu 5/2912:07 pmMBJ - MKE
2 stops23h 20mSpirit Airlines
Deal found 4/16$411

Cheapflights Fare Finder

Customize your flight search to find flights from Milwaukee to Caribbean 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 17, 2025.
Use the filters below to find and compare flights from Milwaukee to Caribbean that are best for you.

Fly from

Milwaukee

Fly to

Caribbean

Route

Depart

Return

Price

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Sun 9/7

4:41 pm-11:15 am

2 stops17h 34m

San Juan Luis Munoz Marin Intl

Sat 9/13

3:55 pm-11:29 pm

1 stop8h 34m

$215

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Sun 5/25

10:00 am-7:48 pm

1 stop8h 48m

San Juan Luis Munoz Marin Intl

Sat 5/31

6:15 am-1:54 pm

1 stop8h 39m

$297

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Mon 5/19

9:15 am-10:38 pm

1 stop12h 23m

San Juan Luis Munoz Marin Intl

Fri 6/6

1:59 am-11:27 am

1 stop10h 28m

$298

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Tue 9/16

7:00 am-2:44 pm

1 stop6h 44m

San Juan Luis Munoz Marin Intl

Mon 9/22

1:05 am-11:30 am

2 stops11h 25m

$305

MilwaukeeSaint Thomas Island

MKE - STT

MKESTT

Milwaukee-Mitchell

Sun 5/25

12:22 pm-1:36 pm

1 stop24h 14m

Saint Thomas Island Cyril E King

Thu 5/29

4:35 pm-11:27 am

1 stop19h 52m

$339

MilwaukeePunta Cana

MKE - PUJ

MKEPUJ

Milwaukee-Mitchell

Sat 5/17

12:22 pm-11:47 am

1 stop22h 25m

Punta Cana

Sat 5/24

12:42 pm-11:27 am

1 stop23h 45m

$341

MilwaukeeProvidenciales

MKE - PLS

MKEPLS

Milwaukee-Mitchell

Sat 8/23

6:53 pm-10:20 am

1 stop14h 27m

Providenciales

Sat 8/30

11:20 am-11:30 pm

1 stop13h 10m

$385

MilwaukeeNassau

MKE - NAS

MKENAS

Milwaukee-Mitchell

Mon 8/25

7:00 am-1:41 pm

1 stop5h 41m

Nassau Intl

Fri 8/29

3:06 pm-11:25 pm

1 stop9h 19m

$399

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Sat 5/17

5:25 am-3:05 pm

2 stops8h 40m

San Juan Luis Munoz Marin Intl

Sat 5/24

7:05 am-3:45 pm

1 stop9h 40m

$400

MilwaukeeNassau

MKE - NAS

MKENAS

Milwaukee-Mitchell

Mon 8/25

7:25 am-4:35 pm

2 stops8h 10m

Nassau Intl

Fri 8/29

11:12 am-5:22 pm

1 stop7h 10m

$403

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/16

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

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

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

Currently, September is the cheapest month in which you can book a flight from Milwaukee to Caribbean (average of $254). Flying from Milwaukee to Caribbean 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 CB?

Find hourly flight availability from Milwaukee to Caribbean. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated April 17, 2025.

When flying from Milwaukee to Caribbean, 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 by month

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

In terms of precipitation, rainfall in Caribbean 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 when rainfall is around 2.2 in.

Temperature in Caribbean by month

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

If weather is an important factor for your trip to Caribbean, 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

Get insights into the airlines that provide service to Caribbean. 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. Reviews last updated April 17, 2025.
Alaska Airlines
8.0
Very good
9,887 reviews

Boarding

8.1

Comfort

7.9

Crew

8.5

Entertainment

7.1

Food

7.1

Overall

8.0

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
9,887 reviews
Alaska Airlines
8.0
Very good
9,887 reviews

Boarding

8.1

Comfort

7.9

Crew

8.5

Entertainment

7.1

Food

7.1

Overall

8.0

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
4,280 reviews
Alaska Airlines
8.0
Very good
9,887 reviews

Boarding

8.1

Comfort

7.9

Crew

8.5

Entertainment

7.1

Food

7.1

Overall

8.0

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
7,916 reviews
Alaska Airlines
8.0
Very good
9,887 reviews

Boarding

8.1

Comfort

7.9

Crew

8.5

Entertainment

7.1

Food

7.1

Overall

8.0

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
8,667 reviews
Alaska Airlines
8.0
Very good
9,887 reviews

Boarding

8.1

Comfort

7.9

Crew

8.5

Entertainment

7.1

Food

7.1

Overall

8.0

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
JetBlue
7.3
Good
2,926 reviews
Alaska Airlines
8.0
Very good
9,887 reviews

Boarding

8.1

Comfort

7.9

Crew

8.5

Entertainment

7.1

Food

7.1

Overall

8.0

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. 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?

    If you book a flight to Caribbean from Milwaukee, you will be flying from 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 Milwaukee to Caribbean one-way?

    One-way options have recently been found by users for as low as $108 on American Airlines. Other airlines that offer cheap prices include Spirit Airlines from $118 and United Airlines from $153 one-way.

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

    The most popular route from Milwaukee to Caribbean is Milwaukee-Mitchell - San Juan Luis Munoz Marin Intl. You may also consider Milwaukee-Mitchell - Punta Cana or Milwaukee-Mitchell - Montego Bay Sangster Intl.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Milwaukee to Caribbean 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?

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

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

Discover the top 8 airlines that operate flights from Milwaukee to Caribbean. 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 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$129Average$245FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$204Average$470FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$248Average$463FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$258Average$564FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$265Average$697FlexibilityNo cancel feeOn-time71%
DeltaCheapest$291Average$545FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$375Average$765FlexibilityNo cancel feeOn-time63%
Sun Country AirCheapest$495Average$646FlexibilityNo cancel feeOn-time83%

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