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Caribbean Islands

$65+ 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 3/10. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SJU
feb. 25 — mar. 41
mar. 2/25
mar. 3/4
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 febrero 20, 2025.

Round-trip from

$194
(CheapOair)

One-way from

$65
(Frontier)

Popular in

December

Cheapest in

September

Average price

$396
From Milwaukee-Mitchell to Caribbean Islands
Search Deals
One-way flight from Milwaukee-Mitchell to Caribbean Islands
Search Deals
Highest demand for flights based on searches. 9% potential increase in price ($46 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($16 potential savings vs. average RT price).
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Average for round-trip flights in February 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 febrero 20, 2025.

This CheapOair deal was found by Cheapflights users on 2/20. 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.
sáb. 4/54:05 pmMKE - STT
1 stop17h 01mSpirit Airlines
mié. 4/910:45 amSTT - MKE
1 stop30h 20mSpirit Airlines
Deal found 2/20$194
This CheapOair deal was found by Cheapflights users on 2/19. 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. 3/36:47 pmMKE - SJU
1 stop19h 40mMultiple Airlines
lun. 3/107:37 pmSJU - MKE
1 stop17h 42mMultiple Airlines
Deal found 2/19$195
This FlightHub deal was found by Cheapflights users on 2/18. 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.
mié. 3/261:24 pmMKE - SJU
1 stop11h 28mSpirit Airlines
mar. 4/19:51 pmSJU - MKE
1 stop12h 18mSpirit Airlines
Deal found 2/18$202
This Cheapflightsfares deal was found by Cheapflights users on 2/19. 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. 3/71:19 pmMKE - SJU
1 stop7h 25mFrontier
dom. 3/165:55 amSJU - MKE
1 stop7h 24mFrontier
Deal found 2/19$208
This American Airlines deal was found by Cheapflights users on 2/19. 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. 5/36:40 amMKE - SJU
2 stops12h 40mAmerican Airlines
mar. 5/67:15 amSJU - MKE
1 stop17h 44mAmerican Airlines
Deal found 2/19$275
This FlightHub deal was found by Cheapflights users on 2/19. 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.
mar. 4/86:29 pmMKE - MBJ
1 stop16h 26mSpirit Airlines
mié. 4/1612:00 pmMBJ - MKE
1 stop28h 05mSpirit Airlines
Deal found 2/19$302
This Delta deal was found by Cheapflights users on 2/20. 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. 3/1110:18 amMKE - SJU
1 stop8h 52mDelta
mié. 3/192:42 pmSJU - MKE
1 stop10h 08mDelta
Deal found 2/20$322
This FlightHub deal was found by Cheapflights users on 2/20. 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.
jue. 5/15:00 pmMKE - PUJ
1 stop20h 42mSpirit Airlines
lun. 5/53:48 pmPUJ - MKE
1 stop20h 49mSpirit Airlines
Deal found 2/20$335
This Kiwi.com deal was found by Cheapflights users on 2/20. 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.
lun. 3/314:05 pmMKE - PUJ
1 stop21h 37mMultiple Airlines
lun. 4/72:46 pmPUJ - MKE
2 stops27h 51mMultiple Airlines
Deal found 2/20$362
This FlightHub deal was found by Cheapflights users on 2/19. 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.
lun. 3/314:05 pmMKE - AUA
1 stop21h 40mSpirit Airlines
sáb. 4/53:50 pmAUA - MKE
2 stops21h 39mSpirit Airlines
Deal found 2/19$375
This Kiwi.com deal was found by Cheapflights users on 2/20. 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.
jue. 4/34:41 pmMKE - MBJ
1 stop18h 21mMultiple Airlines
mié. 4/93:05 pmMBJ - MKE
1 stop25h 00mMultiple Airlines
Deal found 2/20$379
This United Airlines deal was found by Cheapflights users on 2/20. 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.
sáb. 5/311:25 amMKE - SJU
2 stops11h 32mUnited Airlines
lun. 5/51:05 amSJU - MKE
1 stop8h 12mUnited Airlines
Deal found 2/20$385

Find flights from Milwaukee to Caribbean Islands within your budget

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 febrero 20, 2025.

Fly from

Milwaukee

Fly to

Caribbean Islands

Route

Depart

Return

Price

MilwaukeeSaint Thomas Island

MKE - STT

MKESTT

Milwaukee-Mitchell

sáb. 4/5

4:05 pm-10:06 am

1 stop17h 01m

Saint Thomas Island Cyril E King

mié. 4/9

10:45 am-4:05 pm

1 stop30h 20m

$194

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

lun. 3/3

6:47 pm-4:27 pm

1 stop19h 40m

San Juan Luis Munoz Marin Intl

lun. 3/10

7:37 pm-12:19 pm

1 stop17h 42m

$195

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

mié. 3/26

1:24 pm-1:52 am

1 stop11h 28m

San Juan Luis Munoz Marin Intl

mar. 4/1

9:51 pm-9:09 am

1 stop12h 18m

$202

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

vie. 3/7

1:19 pm-10:44 pm

1 stop7h 25m

San Juan Luis Munoz Marin Intl

dom. 3/16

5:55 am-12:19 pm

1 stop7h 24m

$208

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

sáb. 5/3

6:40 am-8:20 pm

2 stops12h 40m

San Juan Luis Munoz Marin Intl

mar. 5/6

7:15 am-11:59 pm

1 stop17h 44m

$275

MilwaukeePunta Cana

MKE - PUJ

MKEPUJ

Milwaukee-Mitchell

sáb. 4/5

4:05 pm-2:42 pm

1 stop21h 37m

Punta Cana

mié. 4/9

3:48 pm-4:05 pm

1 stop25h 17m

$290

MilwaukeePunta Cana

MKE - PUJ

MKEPUJ

Milwaukee-Mitchell

lun. 4/7

8:10 am-1:38 pm

Nonstop4h 28m

Punta Cana

mié. 4/9

3:48 pm-4:05 pm

1 stop25h 17m

$291

MilwaukeeMontego Bay

MKE - MBJ

MKEMBJ

Milwaukee-Mitchell

mar. 4/8

6:29 pm-10:55 am

1 stop16h 26m

Montego Bay Sangster Intl

mié. 4/16

12:00 pm-4:05 pm

1 stop28h 05m

$302

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

mar. 3/11

10:18 am-8:10 pm

1 stop8h 52m

San Juan Luis Munoz Marin Intl

mié. 3/19

2:42 pm-11:50 pm

1 stop10h 08m

$322

MilwaukeeOranjestad

MKE - AUA

MKEAUA

Milwaukee-Mitchell

lun. 3/31

4:05 pm-2:45 pm

1 stop21h 40m

Oranjestad Reina Beatrix

sáb. 4/5

3:50 pm-12:29 pm

2 stops21h 39m

$375

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/18

Showing 1-10 of 44 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.

Travel insights for flights from Milwaukee to Caribbean Islands

Get recent, data-driven insights about flights from Milwaukee to Caribbean Islands including ideal travel times, pricing trends, and more.

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 March is currently the most expensive (average of $363). 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 febrero 20, 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 febrero 20, 2025.
Read through reviews of airlines operating flights from Milwaukee to Caribbean Islands, such as Southwest, Alaska Airlines and Delta. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Overall

8.1

Boarding

8.2

Entertainment

7.6

Food

7.1

Comfort

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Southwest
8.1
Very good
4,411 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Overall

8.1

Boarding

8.2

Entertainment

7.6

Food

7.1

Comfort

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Alaska Airlines
8.0
Very good
9,697 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Overall

8.1

Boarding

8.2

Entertainment

7.6

Food

7.1

Comfort

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Delta
8.0
Very good
8,219 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Overall

8.1

Boarding

8.2

Entertainment

7.6

Food

7.1

Comfort

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

United Airlines
7.4
Good
8,765 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Overall

8.1

Boarding

8.2

Entertainment

7.6

Food

7.1

Comfort

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

American Airlines
7.2
Good
10,000 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Overall

8.1

Boarding

8.2

Entertainment

7.6

Food

7.1

Comfort

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

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 Frontier. According to our data, you can fly for as low as $65. Users have also found prices from $92 and $138 on Spirit Airlines and Delta, 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 - Saint Thomas Island Cyril E King 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 March is currently the most expensive (average of $363). 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 febrero 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$129Average$258FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$157Average$420FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$264Average$656FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$268Average$559FlexibilityNo cancel feeOn-time69%
DeltaCheapest$323Average$531FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$379Average$767FlexibilityNo cancel feeOn-time63%
JetBlueCheapest$397Average$463FlexibilityNo cancel feeOn-time62%
Sun Country AirCheapest$495Average$648FlexibilityNo cancel feeOn-time83%
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