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Caribbean Islands

$113+ 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 7/8. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SJU
Jun 21 — Jun 281
Sat 6/21
Sat 6/28
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 June 16, 2025.

Round-trip from

$225
(Delta)

One-way from

$113
(Southwest)

Popular in

June

Cheapest in

September

Average price

$566
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 ($44 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($12 potential savings vs. average RT price).
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Average for round-trip flights in June 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 June 16, 2025.

This Delta deal was found by Cheapflights users on 6/14. 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 9/162:45 pmMKE - SJU
1 stop6h 23mDelta
Tue 9/235:19 pmSJU - MKE
1 stop7h 06mDelta
Deal found 6/14$225
This United Airlines deal was found by Cheapflights users on 6/15. 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 9/2310:50 amMKE - SJU
2 stops12h 07mUnited Airlines
Tue 10/71:05 amSJU - MKE
2 stops10h 06mUnited Airlines
Deal found 6/15$244
This Southwest deal was found by Cheapflights users on 6/15. 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.
Tue 9/236:05 amMKE - SJU
1 stop10h 20mSouthwest
Wed 10/86:10 amSJU - MKE
1 stop11h 05mSouthwest
Deal found 6/15$270
This FlightHub deal was found by Cheapflights users on 6/15. 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 7/87:03 pmMKE - STT
1 stop16h 27mSpirit Airlines
Tue 7/154:05 pmSTT - MKE
1 stop24h 37mSpirit Airlines
Deal found 6/15$273
This American Airlines deal was found by Cheapflights users on 6/14. 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 11/154:38 pmMKE - SJU
1 stop17h 07mAmerican Airlines
Tue 11/187:25 amSJU - MKE
2 stops11h 53mAmerican Airlines
Deal found 6/14$276
This FlightHub deal was found by Cheapflights users on 6/15. 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.
Thu 7/104:37 pmMKE - SJU
1 stop7h 58mSpirit Airlines
Thu 7/1710:14 pmSJU - MKE
2 stops18h 28mSpirit Airlines
Deal found 6/15$289
This Booking.com deal was found by Cheapflights users on 6/14. 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.
Mon 9/298:51 pmMKE - MBJ
2 stops12h 23mSpirit Airlines
Sat 10/412:11 pmMBJ - MKE
1 stop7h 45mSpirit Airlines
Deal found 6/14$342
This Delta deal was found by Cheapflights users on 6/16. 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.
Tue 7/295:40 amMKE - PUJ
1 stop8h 11mDelta
Thu 8/74:16 pmPUJ - MKE
1 stop8h 43mDelta
Deal found 6/16$351
This American Airlines deal was found by Cheapflights users on 6/14. 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 7/296:20 amMKE - PUJ
1 stop8h 49mAmerican Airlines
Thu 8/74:15 pmPUJ - MKE
2 stops19h 15mAmerican Airlines
Deal found 6/14$355
This FlightHub deal was found by Cheapflights users on 6/15. 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.
Wed 8/206:00 amMKE - PUJ
1 stop28h 45mSpirit Airlines
Tue 8/2612:40 pmPUJ - MKE
1 stop11h 32mSpirit Airlines
Deal found 6/15$357
This Mytrip deal was found by Cheapflights users on 6/14. 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.
Mon 7/712:02 pmMKE - SJU
3 stops35h 03mMultiple Airlines
Sun 7/131:37 amSJU - MKE
2 stops17h 10mMultiple Airlines
Deal found 6/14$408
This Kiwi.com deal was found by Cheapflights users on 6/15. 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.
Sat 7/124:37 pmMKE - PUJ
1 stop15h 17mMultiple Airlines
Sat 7/195:00 pmPUJ - MKE
2 stops45h 56mMultiple Airlines
Deal found 6/15$423

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 June 16, 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

Sat 9/13

10:25 am-10:08 pm

1 stop10h 43m

San Juan Luis Munoz Marin Intl

Sat 9/20

2:28 pm-8:33 pm

1 stop7h 05m

$225

MilwaukeeSaint Thomas Island

MKE - STT

MKESTT

Milwaukee-Mitchell

Tue 7/8

7:03 pm-12:30 pm

1 stop16h 27m

Saint Thomas Island Cyril E King

Tue 7/15

4:05 pm-3:42 pm

1 stop24h 37m

$273

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Sat 8/30

6:32 am-10:49 pm

1 stop15h 17m

San Juan Luis Munoz Marin Intl

Fri 9/5

4:42 pm-10:04 am

2 stops18h 22m

$276

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Thu 7/10

4:37 pm-1:35 am

1 stop7h 58m

San Juan Luis Munoz Marin Intl

Thu 7/17

10:14 pm-3:42 pm

2 stops18h 28m

$289

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Wed 8/27

7:35 am-5:25 pm

2 stops8h 50m

San Juan Luis Munoz Marin Intl

Thu 9/4

3:30 pm-9:25 pm

1 stop6h 55m

$311

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Sun 9/7

6:00 am-2:44 pm

1 stop7h 44m

San Juan Luis Munoz Marin Intl

Fri 9/12

1:05 am-11:30 am

2 stops11h 25m

$315

MilwaukeeMontego Bay

MKE - MBJ

MKEMBJ

Milwaukee-Mitchell

Mon 9/29

8:51 pm-9:14 am

2 stops12h 23m

Montego Bay Sangster Intl

Sat 10/4

12:11 pm-7:56 pm

1 stop7h 45m

$342

MilwaukeePunta Cana

MKE - PUJ

MKEPUJ

Milwaukee-Mitchell

Tue 7/29

5:40 am-2:51 pm

1 stop8h 11m

Punta Cana

Thu 8/7

4:16 pm-11:59 pm

1 stop8h 43m

$351

MilwaukeePunta Cana

MKE - PUJ

MKEPUJ

Milwaukee-Mitchell

Tue 7/29

6:20 am-4:09 pm

1 stop8h 49m

Punta Cana

Thu 8/7

4:15 pm-10:30 am

2 stops19h 15m

$355

MilwaukeePunta Cana

MKE - PUJ

MKEPUJ

Milwaukee-Mitchell

Wed 8/20

6:00 am-11:45 am

1 stop28h 45m

Punta Cana

Tue 8/26

12:40 pm-11:12 pm

1 stop11h 32m

$357

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/16

Showing 1-10 of 53 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 June is currently the most expensive (average of $339). 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 June 16, 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 June 16, 2025.
Read through reviews of airlines operating flights from Milwaukee to Caribbean Islands, such as Southwest, Delta and LATAM Airlines. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,278 reviews

Crew

8.6

Comfort

8.0

Boarding

8.2

Entertainment

7.6

Overall

8.0

Food

7.1

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Southwest
8.0
Very good
4,278 reviews
Southwest
8.0
Very good
4,278 reviews

Crew

8.6

Comfort

8.0

Boarding

8.2

Entertainment

7.6

Overall

8.0

Food

7.1

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Delta
8.0
Very good
7,963 reviews
Southwest
8.0
Very good
4,278 reviews

Crew

8.6

Comfort

8.0

Boarding

8.2

Entertainment

7.6

Overall

8.0

Food

7.1

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
LATAM Airlines
7.5
Good
1,785 reviews
Southwest
8.0
Very good
4,278 reviews

Crew

8.6

Comfort

8.0

Boarding

8.2

Entertainment

7.6

Overall

8.0

Food

7.1

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
United Airlines
7.4
Good
8,801 reviews
Southwest
8.0
Very good
4,278 reviews

Crew

8.6

Comfort

8.0

Boarding

8.2

Entertainment

7.6

Overall

8.0

Food

7.1

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
JetBlue
7.3
Good
2,922 reviews
Southwest
8.0
Very good
4,278 reviews

Crew

8.6

Comfort

8.0

Boarding

8.2

Entertainment

7.6

Overall

8.0

Food

7.1

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

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 Southwest. According to our data, you can fly for as low as $113. Users have also found prices from $115 and $118 on American 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 - 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 June is currently the most expensive (average of $339). 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.

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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 June 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$129Average$239FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$195Average$474FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$225Average$591FlexibilityNo cancel feeOn-time69%
JetBlueCheapest$248Average$445FlexibilityNo cancel feeOn-time62%
DeltaCheapest$268Average$548FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$269Average$726FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$332Average$750FlexibilityNo cancel feeOn-time63%
Sun Country AirCheapest$495Average$647FlexibilityNo cancel feeOn-time83%

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