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$86+ Cheap flights from Milwaukee (MKE) to Caribbean

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
ene. 28 — feb. 41
mié. 1/28
mié. 2/4
1 adult, Economy
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Cheap flight deals from Milwaukee to Caribbean

Cheapest flights from Milwaukee to Caribbean
Explore the most affordable flight options available from Milwaukee to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on diciembre 29, 2025.

This American Airlines deal was found by Cheapflights users on 12/27. 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.
lun. 12/296:14 amMKE - SJU
1 stop15h 08mAmerican Airlines
mié. 12/318:35 pmSJU - MKE
1 stop15h 50mAmerican Airlines
Deal found 12/27$399
This American Airlines deal was found by Cheapflights users on 12/28. 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.
mar. 12/307:10 amMKE - SJU
1 stop12h 55mAmerican Airlines
dom. 1/116:30 amSJU - MKE
1 stop15h 54mAmerican Airlines
Deal found 12/28$407
This American Airlines deal was found by Cheapflights users on 12/27. 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.
mar. 12/308:08 pmMKE - SJU
1 stop17h 00mAmerican Airlines
vie. 1/92:31 pmSJU - MKE
2 stops11h 04mAmerican Airlines
Deal found 12/27$444
This Delta deal was found by Cheapflights users on 12/27. 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.
lun. 12/295:50 pmMKE - PUJ
1 stop16h 51mDelta
mié. 12/314:46 pmPUJ - MKE
1 stop7h 57mDelta
Deal found 12/27$484
This Delta deal was found by Cheapflights users on 12/27. 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. 12/305:40 amMKE - PUJ
1 stop6h 33mDelta
mié. 12/313:23 pmPUJ - MKE
2 stops20h 10mDelta
Deal found 12/27$513
This Delta deal was found by Cheapflights users on 12/29. 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. 12/306:15 pmMKE - PUJ
1 stop16h 13mDelta
jue. 1/13:38 pmPUJ - MKE
1 stop9h 05mDelta
Deal found 12/29$533
This Delta deal was found by Cheapflights users on 12/27. 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.
lun. 12/296:15 pmMKE - PUJ
1 stop16h 13mDelta
jue. 1/14:46 pmPUJ - MKE
1 stop7h 57mDelta
Deal found 12/27$542
This United Airlines deal was found by Cheapflights users on 12/29. 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.
mié. 12/318:00 amMKE - SJU
1 stop11h 26mUnited Airlines
vie. 1/92:05 amSJU - MKE
2 stops12h 04mUnited Airlines
Deal found 12/29$549
This American Airlines deal was found by Cheapflights users on 12/29. 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.
lun. 12/298:08 pmMKE - SJU
1 stop6h 52mAmerican Airlines
sáb. 1/108:20 amSJU - MKE
2 stops12h 06mAmerican Airlines
Deal found 12/29$574
This Delta deal was found by Cheapflights users on 12/29. 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. 12/305:50 pmMKE - PUJ
1 stop16h 51mDelta
lun. 1/53:21 pmPUJ - MKE
1 stop7h 33mDelta
Deal found 12/29$593
This United Airlines deal was found by Cheapflights users on 12/27. 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.
lun. 12/295:00 amMKE - PUJ
1 stop7h 22mUnited Airlines
mar. 12/304:25 pmPUJ - MKE
1 stop7h 48mUnited Airlines
Deal found 12/27$594
This American Airlines deal was found by Cheapflights users on 12/28. 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.
lun. 12/296:00 amMKE - PUJ
1 stop6h 39mAmerican Airlines
mar. 1/66:07 pmPUJ - MKE
2 stops18h 15mAmerican Airlines
Deal found 12/28$599

Find flight deals from Milwaukee to Caribbean

Keep the following information in mind while searching for Milwaukee to Caribbean flight deals. Data was last updated diciembre 29, 2025.

Round-trip from

$235
(United Airlines)

One-way from

$90
(Priceline)

Popular in

December

Cheapest in

September

Average price

$583

Good round-trip deal

$737 or less
From Milwaukee-Mitchell to Caribbean
Search Deals
One-way flight from Milwaukee-Mitchell to Caribbean
Search Deals
Highest demand for flights based on searches. 11% potential increase in price ($59 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($13 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals
Price to beat on a round-trip flight from Milwaukee-Mitchell to Caribbean.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Milwaukee to Caribbean 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 diciembre 29, 2025.
Use the filters below to find and compare flights from Milwaukee to Caribbean that are best for you.

Fly from

Milwaukee

Fly to

Caribbean

Route

Depart

Return

Price

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

lun. 1/19

11:30 am-9:00 pm

1 stop7h 30m

San Juan Luis Munoz Marin Intl

mié. 1/21

2:05 am-1:53 pm

2 stops13h 48m

$235

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

lun. 2/9

7:32 am-9:39 pm

1 stop12h 07m

San Juan Luis Munoz Marin Intl

sáb. 2/14

6:00 am-6:04 pm

1 stop14h 04m

$235

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

mar. 2/3

5:30 am-2:31 pm

1 stop7h 01m

San Juan Luis Munoz Marin Intl

jue. 2/26

6:15 am-2:50 pm

1 stop10h 35m

$235

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

sáb. 1/24

10:30 am-10:22 pm

2 stops9h 52m

San Juan Luis Munoz Marin Intl

vie. 1/30

2:05 am-10:15 am

1 stop10h 10m

$235

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

mié. 3/4

1:35 pm-11:58 pm

1 stop8h 23m

San Juan Luis Munoz Marin Intl

mié. 3/11

6:15 am-12:13 pm

1 stop6h 58m

$235

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

mié. 3/11

10:09 am-8:18 pm

1 stop9h 09m

San Juan Luis Munoz Marin Intl

lun. 3/16

1:17 pm-8:06 pm

1 stop7h 49m

$235

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

lun. 4/20

3:30 pm-11:40 pm

1 stop7h 10m

San Juan Luis Munoz Marin Intl

vie. 4/24

6:50 am-7:10 pm

1 stop13h 20m

$274

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

sáb. 4/18

5:00 am-7:05 pm

1 stop13h 05m

San Juan Luis Munoz Marin Intl

jue. 4/23

5:05 am-4:15 pm

1 stop12h 10m

$305

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

mié. 2/11

11:30 am-9:00 pm

1 stop7h 30m

San Juan Luis Munoz Marin Intl

mar. 2/24

2:05 am-12:35 pm

2 stops12h 30m

$307

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

mar. 1/13

5:30 am-5:17 pm

1 stop9h 47m

San Juan Luis Munoz Marin Intl

mié. 1/21

6:27 pm-11:46 pm

1 stop7h 19m

$317

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/27

Showing 1-10 of 60 results
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Best time to book a flight from Milwaukee to Caribbean

Have a flexible travel schedule? Discover the best time to fly to Caribbean 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

What is the cheapest month to book a flight from Milwaukee to Caribbean?

Currently, November is the cheapest month in which you can book a flight from Milwaukee to Caribbean (average of $113). Flying from Milwaukee to Caribbean 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 CB?

Find hourly flight availability from Milwaukee to Caribbean. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated diciembre 29, 2025.

When flying from Milwaukee to Caribbean, 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

Get insights into the airlines that provide service to Caribbean. 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. Reviews last updated diciembre 29, 2025.
Read through reviews of airlines operating flights from Milwaukee to Caribbean, such as Southwest, Delta, and United Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,250 reviews

Boarding

8.1

Food

7.0

Crew

8.6

Comfort

8.0

Entertainment

7.5

Overall

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
8.0
Very good
4,250 reviews
Southwest
8.0
Very good
4,250 reviews

Boarding

8.1

Food

7.0

Crew

8.6

Comfort

8.0

Entertainment

7.5

Overall

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
8,012 reviews
Southwest
8.0
Very good
4,250 reviews

Boarding

8.1

Food

7.0

Crew

8.6

Comfort

8.0

Entertainment

7.5

Overall

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
9,120 reviews
Southwest
8.0
Very good
4,250 reviews

Boarding

8.1

Food

7.0

Crew

8.6

Comfort

8.0

Entertainment

7.5

Overall

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
11,067 reviews
Southwest
8.0
Very good
4,250 reviews

Boarding

8.1

Food

7.0

Crew

8.6

Comfort

8.0

Entertainment

7.5

Overall

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
337 reviews
Southwest
8.0
Very good
4,250 reviews

Boarding

8.1

Food

7.0

Crew

8.6

Comfort

8.0

Entertainment

7.5

Overall

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. 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?

    If you book a flight to Caribbean from Milwaukee, you will be flying from Milwaukee-Mitchell, which is the city’s only airport. Milwaukee-Mitchell (MKE) is located 6.4 mi from the center of Milwaukee.

  • How long is the flight from Milwaukee to Caribbean?

    A quick flight from Milwaukee to Caribbean can take about 7h 01m. United Airlines provides one of the quickest options available for as low as $235. Airlines will cover a distance of 2120 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines to fly from Milwaukee to Caribbean one-way?

    One-way options have recently been found by users for as low as $43 on Frontier. Other airlines that offer cheap prices include United Airlines from $108 and Southwest from $108 one-way.

  • What are the most popular routes from Milwaukee to Caribbean?

    The most popular route from Milwaukee to Caribbean is Milwaukee-Mitchell - San Juan Luis Munoz Marin Intl. You may also consider Milwaukee-Mitchell - Punta Cana or Milwaukee-Mitchell - Saint Thomas Island Cyril E King.

  • Can I find deals for flights from Milwaukee to Caribbean that include hotel bookings?

    Yes. In addition to deals on Milwaukee to Caribbean flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Milwaukee to Caribbean?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Milwaukee to Caribbean.

  • Can I find deals for business class flights from Milwaukee to Caribbean?

    Yes. Cheapflights offers flight deals from Milwaukee to Caribbean 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?

    Currently, November is the cheapest month in which you can book a flight from Milwaukee to Caribbean (average of $113). Flying from Milwaukee to Caribbean 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

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Milwaukee to Caribbean

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

Discover the top 7 airlines that operate flights from Milwaukee to Caribbean. 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 diciembre 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$129Average$254FlexibilityNo cancel feeOn-time62%
DeltaCheapest$188Average$588FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$215Average$560FlexibilityNo cancel feeOn-time69%
Spirit AirlinesCheapest$226Average$403FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$270Average$679FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$315Average$745FlexibilityNo cancel feeOn-time63%
Sun Country AirCheapest$497Average$652FlexibilityNo cancel feeOn-time83%

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