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Caribbean Islands

$86+ 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 2/7. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SJU
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
1 adult, Economy
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Cheap 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 December 18, 2025.

This Priceline deal was found by Cheapflights users on 12/17. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/207:48 pmMKE - SJU
1 stop29h 02mFrontier
Thu 12/259:37 pmSJU - MKE
1 stop21h 44mFrontier
Deal found 12/17$264
This Priceline deal was found by Cheapflights users on 12/16. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/218:06 pmMKE - SJU
1 stop28h 44mFrontier
Thu 12/259:37 pmSJU - MKE
1 stop21h 44mFrontier
Deal found 12/16$314
This Frontier deal was found by Cheapflights users on 12/15. 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.
Sat 12/207:48 pmMKE - SJU
1 stop11h 10mFrontier
Sun 12/213:55 amSJU - MKE
1 stop9h 18mFrontier
Deal found 12/15$334
This Priceline deal was found by Cheapflights users on 12/17. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/218:06 pmMKE - SJU
1 stop11h 17mFrontier
Tue 12/236:00 amSJU - MKE
1 stop14h 26mFrontier
Deal found 12/17$355
This Travelocity deal was found by Cheapflights users on 12/15. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/237:21 pmMKE - SJU
1 stop23h 06mFrontier
Fri 12/2610:33 amSJU - MKE
1 stop8h 48mFrontier
Deal found 12/15$359
This Frontier deal was found by Cheapflights users on 12/15. 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.
Sat 12/207:48 pmMKE - SJU
1 stop11h 10mFrontier
Tue 12/2310:33 amSJU - MKE
1 stop9h 53mFrontier
Deal found 12/15$375
This Priceline deal was found by Cheapflights users on 12/17. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/218:06 pmMKE - SJU
1 stop11h 17mFrontier
Fri 12/263:55 amSJU - MKE
1 stop17h 08mFrontier
Deal found 12/17$389
This American Airlines deal was found by Cheapflights users on 12/16. 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.
Tue 12/306:27 pmMKE - SJU
1 stop15h 12mAmerican Airlines
Fri 1/96:30 amSJU - MKE
1 stop15h 54mAmerican Airlines
Deal found 12/16$390
This United Airlines deal was found by Cheapflights users on 12/17. 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.
Thu 12/187:08 amMKE - SJU
2 stops12h 18mUnited Airlines
Sun 12/217:45 amSJU - MKE
1 stop9h 07mUnited Airlines
Deal found 12/17$399
This Priceline deal was found by Cheapflights users on 12/15. 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.
Fri 12/2610:48 amMKE - SJU
1 stop9h 56mFrontier
Mon 12/299:37 pmSJU - MKE
1 stop22h 49mFrontier
Deal found 12/15$405
This Priceline deal was found by Cheapflights users on 12/15. 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.
Sat 12/207:48 pmMKE - SJU
1 stop11h 10mFrontier
Sat 12/279:49 amSJU - MKE
1 stop11h 14mFrontier
Deal found 12/15$409
This Delta deal was found by Cheapflights users on 12/16. 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.
Wed 12/175:45 amMKE - PUJ
1 stop6h 40mDelta
Mon 12/224:46 pmPUJ - MKE
1 stop9h 05mDelta
Deal found 12/16$434

Find 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 December 18, 2025.

Round-trip from

$235
(Delta)

One-way from

$86
(Priceline)

Popular in

June

Cheapest in

September

Average price

$532
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 ($48 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($12 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

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 December 18, 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

Sun 1/4

8:06 pm-2:50 am

1 stop28h 44m

San Juan Luis Munoz Marin Intl

Sat 1/10

6:15 am-7:14 pm

1 stop14h 59m

$235

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Tue 3/3

6:00 am-4:52 pm

2 stops8h 52m

San Juan Luis Munoz Marin Intl

Tue 3/10

3:12 pm-11:18 pm

1 stop9h 06m

$235

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Tue 2/10

5:30 am-2:31 pm

1 stop7h 01m

San Juan Luis Munoz Marin Intl

Sat 2/14

6:15 am-1:16 pm

1 stop9h 01m

$235

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Tue 3/3

6:00 am-3:40 pm

1 stop7h 40m

San Juan Luis Munoz Marin Intl

Tue 3/10

1:05 am-12:35 pm

2 stops12h 30m

$235

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Tue 1/13

8:33 am-9:26 pm

2 stops10h 53m

San Juan Luis Munoz Marin Intl

Tue 1/20

2:05 am-10:46 am

1 stop10h 41m

$253

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Thu 1/8

7:30 pm-8:54 am

1 stop11h 24m

San Juan Luis Munoz Marin Intl

Sat 1/17

8:57 am-6:47 pm

1 stop11h 50m

$289

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Mon 2/2

11:30 am-12:36 am

2 stops11h 06m

San Juan Luis Munoz Marin Intl

Fri 2/6

2:15 pm-9:59 pm

2 stops9h 44m

$303

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Thu 2/19

12:20 pm-11:58 pm

1 stop9h 38m

San Juan Luis Munoz Marin Intl

Wed 2/25

7:30 am-12:31 pm

1 stop7h 01m

$305

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Sat 1/31

7:48 pm-9:54 am

1 stop12h 06m

San Juan Luis Munoz Marin Intl

Sat 2/7

8:00 am-6:53 pm

1 stop12h 53m

$306

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Wed 3/11

7:30 am-8:49 pm

2 stops12h 19m

San Juan Luis Munoz Marin Intl

Sun 3/15

1:30 am-11:01 am

1 stop10h 31m

$308

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/16

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, November is the cheapest month in which you can book a flight from Milwaukee to Caribbean Islands (average of $113). Flying from Milwaukee to Caribbean Islands in December is currently the most expensive (average of $221). 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 December 18, 2025.

It’s optimal to fly from Milwaukee to Caribbean Islands at noon. By choosing this option you can save up to 41% on the cost of your flight, compared to a flight in the morning.

What is the cheapest day to fly from Milwaukee to Caribbean Islands?

Use this chart to determine the cheapest time to fly round-trip from Milwaukee to Caribbean Islands. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Milwaukee to Caribbean Islands flight should consider departing on Saturday at noon when fares are most often at their lowest. Sunday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

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 December 18, 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
7.9
Good
4,251 reviews

Entertainment

7.5

Food

7.0

Crew

8.6

Boarding

8.1

Overall

7.9

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
7.9
Good
4,251 reviews
Southwest
7.9
Good
4,251 reviews

Entertainment

7.5

Food

7.0

Crew

8.6

Boarding

8.1

Overall

7.9

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Delta
7.9
Good
8,009 reviews
Southwest
7.9
Good
4,251 reviews

Entertainment

7.5

Food

7.0

Crew

8.6

Boarding

8.1

Overall

7.9

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
United Airlines
7.4
Good
9,095 reviews
Southwest
7.9
Good
4,251 reviews

Entertainment

7.5

Food

7.0

Crew

8.6

Boarding

8.1

Overall

7.9

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
American Airlines
7.2
Good
11,054 reviews
Southwest
7.9
Good
4,251 reviews

Entertainment

7.5

Food

7.0

Crew

8.6

Boarding

8.1

Overall

7.9

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Sun Country Air
6.9
Okay
333 reviews
Southwest
7.9
Good
4,251 reviews

Entertainment

7.5

Food

7.0

Crew

8.6

Boarding

8.1

Overall

7.9

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

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?

    Frontier, American Airlines, and Delta can get you from Milwaukee to Caribbean Islands in just under 7h 01m. Your travel time can differ by up to 21h 43m. 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 Frontier. According to our data, you can fly for as low as $43. Users have also found prices from $108 and $108 on United Airlines and Southwest, 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 - Montego Bay Sangster Intl 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, November is the cheapest month in which you can book a flight from Milwaukee to Caribbean Islands (average of $113). Flying from Milwaukee to Caribbean Islands in December is currently the most expensive (average of $221). 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 December 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$129Average$256FlexibilityNo cancel feeOn-time62%
DeltaCheapest$191Average$588FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$215Average$566FlexibilityNo cancel feeOn-time69%
Spirit AirlinesCheapest$226Average$406FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$274Average$680FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$315Average$754FlexibilityNo cancel feeOn-time63%
Sun Country AirCheapest$497Average$652FlexibilityNo cancel feeOn-time83%

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