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$113+ 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
may. 6 — may. 131
mar. 5/6
mar. 5/13
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 mayo 1, 2025.

Round-trip from

$225
(Delta)

One-way from

$113
(Delta)

Popular in

December

Cheapest in

September

Average price

$366
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. 3% potential price decrease ($17 potential savings vs. average RT price).
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Average for round-trip flights in May 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 mayo 1, 2025.

This Delta deal was found by Cheapflights users on 4/28. 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.
sáb. 11/157:00 amMKE - SJU
1 stop8h 10mDelta
mar. 11/183:25 pmSJU - MKE
1 stop7h 43mDelta
Deal found 4/28$225
This United Airlines deal was found by Cheapflights users on 4/30. 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.
mié. 9/177:00 amMKE - SJU
1 stop6h 44mUnited Airlines
sáb. 9/201:05 amSJU - MKE
2 stops10h 08mUnited Airlines
Deal found 4/30$254
This American Airlines deal was found by Cheapflights users on 4/29. 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.
mar. 9/165:20 amMKE - SJU
2 stops10h 00mAmerican Airlines
mar. 9/233:55 pmSJU - MKE
1 stop8h 34mAmerican Airlines
Deal found 4/29$302
This Cheapflightsfares deal was found by Cheapflights users on 4/30. 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.
vie. 5/1612:22 pmMKE - SJU
1 stop11h 32mSpirit Airlines
sáb. 5/241:59 amSJU - MKE
1 stop10h 28mSpirit Airlines
Deal found 4/30$306
This Mytrip deal was found by Cheapflights users on 4/29. 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.
mar. 6/1012:22 pmMKE - MBJ
2 stops22h 40mSpirit Airlines
mar. 6/1712:07 pmMBJ - MKE
2 stops30h 02mSpirit Airlines
Deal found 4/29$361
This CheapOair deal was found by Cheapflights users on 4/30. 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.
lun. 5/1912:22 pmMKE - SJU
1 stop11h 32mMultiple Airlines
sáb. 6/74:20 pmSJU - MKE
1 stop26h 09mMultiple Airlines
Deal found 4/30$385
This Kiwi.com deal was found by Cheapflights users on 4/30. 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.
mar. 6/1012:22 pmMKE - PUJ
2 stops23h 33mSpirit Airlines
mar. 6/1712:34 pmPUJ - MKE
1 stop30h 35mSpirit Airlines
Deal found 4/30$402
This Mytrip deal was found by Cheapflights users on 4/29. 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.
vie. 5/1612:22 pmMKE - STT
1 stop24h 14mSpirit Airlines
mar. 5/202:41 pmSTT - MKE
1 stop21h 46mSpirit Airlines
Deal found 4/29$428
This Delta deal was found by Cheapflights users on 4/29. 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.
mar. 8/196:00 amMKE - PLS
1 stop5h 45mDelta
mar. 8/262:05 pmPLS - MKE
1 stop10h 20mDelta
Deal found 4/29$438
This American Airlines deal was found by Cheapflights users on 4/30. 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.
mié. 5/217:07 amMKE - NAS
1 stop5h 38mAmerican Airlines
vie. 5/3012:05 pmNAS - MKE
1 stop10h 05mAmerican Airlines
Deal found 4/30$449
This Delta deal was found by Cheapflights users on 4/29. 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.
dom. 11/96:00 amMKE - PUJ
1 stop6h 23mDelta
vie. 11/144:55 pmPUJ - MKE
1 stop8h 30mDelta
Deal found 4/29$455
This American Airlines deal was found by Cheapflights users on 4/29. 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.
sáb. 10/255:43 pmMKE - PUJ
2 stops17h 52mAmerican Airlines
sáb. 11/15:25 pmPUJ - MKE
2 stops19h 09mAmerican Airlines
Deal found 4/29$459

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 mayo 1, 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

mar. 9/16

2:45 pm-10:08 pm

1 stop6h 23m

San Juan Luis Munoz Marin Intl

mar. 9/23

5:19 pm-11:25 pm

1 stop7h 06m

$225

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

mié. 9/17

7:00 am-2:44 pm

1 stop6h 44m

San Juan Luis Munoz Marin Intl

sáb. 9/20

1:05 am-10:13 am

2 stops10h 08m

$254

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

mar. 9/16

5:20 am-4:20 pm

2 stops10h 00m

San Juan Luis Munoz Marin Intl

mar. 9/23

3:55 pm-11:29 pm

1 stop8h 34m

$302

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

vie. 5/16

12:22 pm-12:54 am

1 stop11h 32m

San Juan Luis Munoz Marin Intl

sáb. 5/24

1:59 am-11:27 am

1 stop10h 28m

$306

MilwaukeeSaint Thomas Island

MKE - STT

MKESTT

Milwaukee-Mitchell

jue. 5/29

12:22 pm-1:36 pm

1 stop24h 14m

Saint Thomas Island Cyril E King

dom. 6/1

1:21 pm-11:27 am

1 stop23h 06m

$330

MilwaukeeMontego Bay

MKE - MBJ

MKEMBJ

Milwaukee-Mitchell

mar. 6/10

12:22 pm-11:02 am

2 stops22h 40m

Montego Bay Sangster Intl

mar. 6/17

12:07 pm-6:09 pm

2 stops30h 02m

$361

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

lun. 5/19

12:22 pm-12:54 am

1 stop11h 32m

San Juan Luis Munoz Marin Intl

sáb. 6/7

4:20 pm-5:29 pm

1 stop26h 09m

$385

MilwaukeePunta Cana

MKE - PUJ

MKEPUJ

Milwaukee-Mitchell

mar. 6/10

12:22 pm-12:55 pm

2 stops23h 33m

Punta Cana

mar. 6/17

12:34 pm-6:09 pm

1 stop30h 35m

$402

MilwaukeeProvidenciales

MKE - PLS

MKEPLS

Milwaukee-Mitchell

mar. 8/19

6:00 am-12:45 pm

1 stop5h 45m

Providenciales

mar. 8/26

2:05 pm-11:25 pm

1 stop10h 20m

$438

MilwaukeeNassau

MKE - NAS

MKENAS

Milwaukee-Mitchell

mié. 5/21

7:07 am-1:45 pm

1 stop5h 38m

Nassau Intl

vie. 5/30

12:05 pm-9:10 pm

1 stop10h 05m

$449

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

Showing 1-10 of 41 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 mayo 1, 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 mayo 1, 2025.
Alaska Airlines
8.0
Very good
9,968 reviews

Boarding

8.2

Overall

8.0

Entertainment

7.1

Crew

8.5

Comfort

7.9

Food

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Alaska Airlines
8.0
Very good
9,968 reviews
Alaska Airlines
8.0
Very good
9,968 reviews

Boarding

8.2

Overall

8.0

Entertainment

7.1

Crew

8.5

Comfort

7.9

Food

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Southwest
8.0
Very good
4,294 reviews
Alaska Airlines
8.0
Very good
9,968 reviews

Boarding

8.2

Overall

8.0

Entertainment

7.1

Crew

8.5

Comfort

7.9

Food

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Delta
8.0
Very good
7,934 reviews
Alaska Airlines
8.0
Very good
9,968 reviews

Boarding

8.2

Overall

8.0

Entertainment

7.1

Crew

8.5

Comfort

7.9

Food

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
LATAM Airlines
7.5
Good
1,767 reviews
Alaska Airlines
8.0
Very good
9,968 reviews

Boarding

8.2

Overall

8.0

Entertainment

7.1

Crew

8.5

Comfort

7.9

Food

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
United Airlines
7.4
Good
8,696 reviews
Alaska Airlines
8.0
Very good
9,968 reviews

Boarding

8.2

Overall

8.0

Entertainment

7.1

Crew

8.5

Comfort

7.9

Food

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

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 $113 on Delta. Other airlines that offer cheap prices include American Airlines from $139 and Spirit Airlines from $147 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 - Saint Thomas Island Cyril E King.

  • 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 mayo 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$129Average$244FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$204Average$452FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$233Average$567FlexibilityNo cancel feeOn-time69%
JetBlueCheapest$248Average$463FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$267Average$711FlexibilityNo cancel feeOn-time71%
DeltaCheapest$286Average$540FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$343Average$765FlexibilityNo cancel feeOn-time63%
Sun Country AirCheapest$495Average$646FlexibilityNo cancel feeOn-time83%

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