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Caribbean Islands

$118+ 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 11/17. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SJU
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
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 September 15, 2025.

Round-trip from

$235
(American Airlines)

One-way from

$118
(Delta)

Popular in

June

Cheapest in

September

Average price

$317
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 ($47 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 September 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 September 15, 2025.

This Delta deal was found by Cheapflights users on 9/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/285:47 amMKE - SJU
1 stop9h 46mDelta
Tue 11/47:15 amSJU - MKE
1 stop11h 03mDelta
Deal found 9/15$235
This American Airlines deal was found by Cheapflights users on 9/15. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/96:14 amMKE - SJU
1 stop12h 44mAmerican Airlines
Fri 11/148:20 amSJU - MKE
1 stop8h 49mAmerican Airlines
Deal found 9/15$295
This Delta deal was found by Cheapflights users on 9/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/172:04 pmMKE - SJU
1 stop6h 55mDelta
Thu 10/237:15 amSJU - MKE
1 stop9h 36mDelta
Deal found 9/15$305
This Frontier deal was found by Cheapflights users on 9/15. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/57:48 pmMKE - SJU
1 stop12h 07mFrontier
Fri 12/1211:05 amSJU - MKE
1 stop9h 48mFrontier
Deal found 9/15$312
This American Airlines deal was found by Cheapflights users on 9/14. 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 11/46:15 amMKE - SJU
1 stop8h 50mAmerican Airlines
Sat 11/88:00 amSJU - MKE
2 stops12h 27mAmerican Airlines
Deal found 9/14$317
This United Airlines deal was found by Cheapflights users on 9/15. 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.
Wed 10/296:05 amMKE - SJU
2 stops14h 17mUnited Airlines
Sat 11/17:10 amSJU - MKE
1 stop7h 48mUnited Airlines
Deal found 9/15$325
This Priceline deal was found by Cheapflights users on 9/15. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/311:57 amMKE - SJU
1 stop9h 22mMultiple Airlines
Mon 12/811:05 amSJU - MKE
1 stop9h 48mMultiple Airlines
Deal found 9/15$334
This Cheapflightsfares deal was found by Cheapflights users on 9/15. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/311:57 amMKE - SJU
1 stop9h 22mSpirit Airlines
Sun 12/72:59 amSJU - MKE
1 stop11h 52mSpirit Airlines
Deal found 9/15$344
This Delta deal was found by Cheapflights users on 9/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/77:00 amMKE - SJU
1 stop8h 19mDelta
Fri 12/126:36 pmSJU - MKE
1 stop7h 20mDelta
Deal found 9/15$350
This Delta deal was found by Cheapflights users on 9/14. 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.
Wed 10/295:47 amMKE - PUJ
1 stop6h 37mDelta
Wed 11/53:49 pmPUJ - MKE
1 stop10h 06mDelta
Deal found 9/14$352
This American Airlines deal was found by Cheapflights users on 9/14. 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.
Sun 11/96:12 amMKE - PUJ
1 stop8h 34mAmerican Airlines
Fri 11/145:24 pmPUJ - MKE
1 stop7h 32mAmerican Airlines
Deal found 9/14$353
This American Airlines deal was found by Cheapflights users on 9/14. 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 10/184:59 pmMKE - PUJ
2 stops18h 48mAmerican Airlines
Thu 10/231:48 pmPUJ - MKE
2 stops10h 42mAmerican Airlines
Deal found 9/14$355

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 September 15, 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

Thu 10/30

10:35 am-9:59 pm

1 stop10h 24m

San Juan Luis Munoz Marin Intl

Thu 11/6

7:15 am-4:19 pm

1 stop11h 04m

$235

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Tue 10/28

6:05 am-2:40 pm

1 stop7h 35m

San Juan Luis Munoz Marin Intl

Mon 11/3

2:05 am-10:19 am

1 stop10h 14m

$235

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Tue 10/28

2:04 pm-9:59 pm

1 stop6h 55m

San Juan Luis Munoz Marin Intl

Thu 11/6

7:15 am-4:19 pm

1 stop11h 04m

$235

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Fri 10/31

7:00 am-4:25 pm

1 stop8h 25m

San Juan Luis Munoz Marin Intl

Wed 11/5

6:43 pm-11:55 pm

1 stop7h 12m

$305

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Mon 10/27

5:47 am-4:33 pm

1 stop9h 46m

San Juan Luis Munoz Marin Intl

Tue 11/4

7:15 am-1:09 pm

1 stop7h 54m

$305

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Fri 10/31

7:00 am-4:25 pm

1 stop8h 25m

San Juan Luis Munoz Marin Intl

Thu 11/6

7:15 am-4:19 pm

1 stop11h 04m

$305

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Mon 10/27

5:47 am-4:33 pm

1 stop9h 46m

San Juan Luis Munoz Marin Intl

Thu 11/6

7:15 am-4:19 pm

1 stop11h 04m

$305

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Sun 12/7

10:25 am-11:10 pm

1 stop10h 45m

San Juan Luis Munoz Marin Intl

Fri 12/12

6:36 pm-11:56 pm

1 stop7h 20m

$350

MilwaukeePunta Cana

MKE - PUJ

MKEPUJ

Milwaukee-Mitchell

Mon 1/12

5:45 am-4:40 pm

1 stop8h 55m

Punta Cana

Thu 1/15

6:05 pm-9:27 am

1 stop17h 22m

$353

MilwaukeePunta Cana

MKE - PUJ

MKEPUJ

Milwaukee-Mitchell

Sun 1/11

5:45 am-4:40 pm

1 stop8h 55m

Punta Cana

Fri 1/16

5:11 pm-10:11 am

1 stop19h 00m

$353

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/13

Showing 1-10 of 60 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 September 15, 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.

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 September 15, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta, and United Airlines from Milwaukee to Caribbean Islands to help guide your decision. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Overall

8.0

Comfort

8.0

Boarding

8.1

Crew

8.6

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Overall

8.0

Comfort

8.0

Boarding

8.1

Crew

8.6

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Delta
8.0
Very good
7,954 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Overall

8.0

Comfort

8.0

Boarding

8.1

Crew

8.6

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
8,929 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Overall

8.0

Comfort

8.0

Boarding

8.1

Crew

8.6

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Overall

8.0

Comfort

8.0

Boarding

8.1

Crew

8.6

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Sun Country Air
6.9
Okay
330 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Overall

8.0

Comfort

8.0

Boarding

8.1

Crew

8.6

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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.

  • How long is the flight from Milwaukee to Caribbean Islands?

    Delta, United Airlines, and Spirit Airlines can get you from Milwaukee to Caribbean Islands in just under 7h 35m. Your travel time can differ by up to 15h 40m. The distance from Milwaukee to Caribbean Islands is about 2120 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • 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 $118. Users have also found prices from $121 and $163 on American Airlines and United 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 - 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 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.

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 7 airlines flying from Milwaukee to Caribbean Islands

Discover the top 7 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 September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$129Average$230FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$208Average$391FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$215Average$584FlexibilityNo cancel feeOn-time69%
DeltaCheapest$215Average$579FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$275Average$679FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$315Average$750FlexibilityNo cancel feeOn-time63%
Sun Country AirCheapest$540Average$652FlexibilityNo cancel feeOn-time83%

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