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Caribbean Islands

$69+ 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 2/11. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SJU
Dec 3 — Dec 101
Wed 12/3
Wed 12/10
1 adult, Economy
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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 November 3, 2025.

This Expedia deal was found by Cheapflights users on 11/2. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/510:34 amMKE - SJU
1 stop11h 42mMultiple Airlines
Sat 12/133:55 amSJU - MKE
1 stop15h 14mMultiple Airlines
Deal found 11/2$256
This United Airlines deal was found by Cheapflights users on 11/3. 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 12/912:04 pmMKE - SJU
1 stop6h 56mUnited Airlines
Mon 12/152:05 amSJU - MKE
2 stops11h 24mUnited Airlines
Deal found 11/3$300
This American Airlines deal was found by Cheapflights users on 11/2. 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 12/711:57 amMKE - SJU
1 stop15h 22mAmerican Airlines
Fri 12/125:56 pmSJU - MKE
1 stop7h 05mAmerican Airlines
Deal found 11/2$308
This American Airlines deal was found by Cheapflights users on 11/1. 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.
Fri 11/288:13 amMKE - SJU
2 stops14h 31mAmerican Airlines
Sat 12/68:18 amSJU - MKE
2 stops13h 02mAmerican Airlines
Deal found 11/1$314
This American Airlines deal was found by Cheapflights users on 11/1. 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.
Thu 11/136:48 pmMKE - SJU
2 stops13h 29mAmerican Airlines
Wed 11/267:15 amSJU - MKE
1 stop11h 50mAmerican Airlines
Deal found 11/1$317
This American Airlines deal was found by Cheapflights users on 11/2. 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 11/236:14 amMKE - SJU
1 stop12h 44mAmerican Airlines
Tue 11/257:15 amSJU - MKE
1 stop16h 16mAmerican Airlines
Deal found 11/2$335
This CheapOair deal was found by Cheapflights users on 10/31. 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.
Tue 12/308:15 pmMKE - SJU
1 stop16h 05mSpirit Airlines
Fri 1/96:00 amSJU - MKE
1 stop7h 29mSpirit Airlines
Deal found 10/31$336
This Southwest deal was found by Cheapflights users on 11/2. 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 12/211:05 amMKE - SJU
1 stop11h 30mSouthwest
Tue 12/911:20 amSJU - MKE
1 stop7h 05mSouthwest
Deal found 11/2$344
This Southwest deal was found by Cheapflights users on 11/1. 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.
Mon 11/1710:30 amMKE - SJU
2 stops12h 05mSouthwest
Thu 11/275:45 amSJU - MKE
1 stop9h 35mSouthwest
Deal found 11/1$356
This Delta deal was found by Cheapflights users on 11/2. 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.
Sat 12/65:45 amMKE - PLS
1 stop7h 09mDelta
Sat 12/132:10 pmPLS - MKE
1 stop10h 30mDelta
Deal found 11/2$364
This United Airlines deal was found by Cheapflights users on 11/1. 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.
Sat 12/65:00 amMKE - PLS
1 stop7h 55mUnited Airlines
Sat 12/135:06 pmPLS - MKE
2 stops18h 13mUnited Airlines
Deal found 11/1$369
This American Airlines deal was found by Cheapflights users on 11/2. 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 12/146:28 pmMKE - PLS
2 stops16h 39mAmerican Airlines
Sun 12/214:00 pmPLS - MKE
1 stop8h 00mAmerican Airlines
Deal found 11/2$374

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 November 3, 2025.

Round-trip from

$235
(United Airlines)

One-way from

$84
(Frontier)

Popular in

June

Cheapest in

September

Average price

$517
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. 10% potential increase in price ($53 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($14 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 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 November 3, 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

Wed 2/4

8:33 am-9:26 pm

2 stops10h 53m

San Juan Luis Munoz Marin Intl

Fri 2/6

2:15 pm-9:59 pm

2 stops9h 44m

$235

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Tue 2/3

7:02 am-4:52 pm

1 stop7h 50m

San Juan Luis Munoz Marin Intl

Thu 2/26

6:15 am-11:15 am

1 stop7h 00m

$235

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Tue 2/3

11:30 am-9:00 pm

1 stop7h 30m

San Juan Luis Munoz Marin Intl

Fri 2/6

2:05 am-1:53 pm

2 stops13h 48m

$235

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Sun 1/25

10:13 am-8:57 pm

1 stop8h 44m

San Juan Luis Munoz Marin Intl

Wed 2/4

6:27 pm-11:46 pm

1 stop7h 19m

$235

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Tue 2/3

11:35 am-12:35 am

1 stop11h 00m

San Juan Luis Munoz Marin Intl

Sat 2/7

5:30 am-2:40 pm

2 stops11h 10m

$300

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Tue 1/6

7:02 am-4:52 pm

1 stop7h 50m

San Juan Luis Munoz Marin Intl

Thu 2/5

2:15 pm-8:48 pm

1 stop8h 33m

$300

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Tue 12/9

12:04 pm-9:00 pm

1 stop6h 56m

San Juan Luis Munoz Marin Intl

Mon 12/15

2:05 am-11:29 am

2 stops11h 24m

$300

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Tue 3/10

8:30 am-9:22 pm

2 stops11h 52m

San Juan Luis Munoz Marin Intl

Tue 3/10

1:05 am-12:35 pm

2 stops12h 30m

$320

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Tue 2/3

7:50 am-9:26 pm

1 stop11h 36m

San Juan Luis Munoz Marin Intl

Mon 2/9

2:05 am-3:43 pm

2 stops15h 38m

$325

MilwaukeeProvidenciales

MKE - PLS

MKEPLS

Milwaukee-Mitchell

Sat 12/6

7:00 am-1:54 pm

1 stop5h 54m

Providenciales

Sat 12/13

2:10 pm-11:40 pm

1 stop10h 30m

$364

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/1

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, February is the cheapest month in which you can book a flight from Milwaukee to Caribbean Islands (average of $127). Flying from Milwaukee to Caribbean Islands in December is currently the most expensive (average of $188). 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 November 3, 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 November 3, 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
4,238 reviews

Food

7.0

Boarding

8.1

Crew

8.6

Overall

8.0

Entertainment

7.5

Comfort

8.0

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
4,238 reviews
Southwest
8.0
Very good
4,238 reviews

Food

7.0

Boarding

8.1

Crew

8.6

Overall

8.0

Entertainment

7.5

Comfort

8.0

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
7.9
Good
8,001 reviews
Southwest
8.0
Very good
4,238 reviews

Food

7.0

Boarding

8.1

Crew

8.6

Overall

8.0

Entertainment

7.5

Comfort

8.0

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
8,997 reviews
Southwest
8.0
Very good
4,238 reviews

Food

7.0

Boarding

8.1

Crew

8.6

Overall

8.0

Entertainment

7.5

Comfort

8.0

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
11,036 reviews
Southwest
8.0
Very good
4,238 reviews

Food

7.0

Boarding

8.1

Crew

8.6

Overall

8.0

Entertainment

7.5

Comfort

8.0

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
334 reviews
Southwest
8.0
Very good
4,238 reviews

Food

7.0

Boarding

8.1

Crew

8.6

Overall

8.0

Entertainment

7.5

Comfort

8.0

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?

    Southwest, United Airlines, and Delta can get you from Milwaukee to Caribbean Islands in just under 7h 50m. Your travel time can differ by up to 3h 10m. 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 $84. Users have also found prices from $118 and $138 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, February is the cheapest month in which you can book a flight from Milwaukee to Caribbean Islands (average of $127). Flying from Milwaukee to Caribbean Islands in December is currently the most expensive (average of $188). 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 November 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$129Average$243FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$202Average$560FlexibilityNo cancel feeOn-time69%
DeltaCheapest$215Average$585FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$226Average$407FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$275Average$685FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$315Average$764FlexibilityNo cancel feeOn-time63%
Sun Country AirCheapest$540Average$651FlexibilityNo cancel feeOn-time83%

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