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$90+ 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 2/14. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SJU
Dec 29 — Jan 51
Mon 12/29
Mon 1/5
1 adult, Economy
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Find 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 November 29, 2025.

This Kiwi.com deal was found by Cheapflights users on 11/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/56:09 pmMKE - SJU
1 stop28h 07mMultiple Airlines
Sat 12/134:10 amSJU - MKE
2 stops14h 59mMultiple Airlines
Deal found 11/29$309
This Kiwi.com deal was found by Cheapflights users on 11/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/56:09 pmMKE - SJU
1 stop30h 41mMultiple Airlines
Wed 12/103:55 amSJU - MKE
1 stop7h 44mMultiple Airlines
Deal found 11/27$311
This American Airlines deal was found by Cheapflights users on 11/27. 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.
Tue 12/96:15 amMKE - SJU
1 stop13h 54mAmerican Airlines
Sat 12/206:44 amSJU - MKE
1 stop17h 16mAmerican Airlines
Deal found 11/27$317
This Kiwi.com deal was found by Cheapflights users on 11/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/810:34 amMKE - SJU
2 stops12h 11mMultiple Airlines
Thu 12/113:55 amSJU - MKE
1 stop15h 14mMultiple Airlines
Deal found 11/28$321
This Kiwi.com deal was found by Cheapflights users on 11/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/710:34 amMKE - SJU
1 stop14h 16mMultiple Airlines
Thu 12/115:00 pmSJU - MKE
1 stop18h 39mMultiple Airlines
Deal found 11/27$325
This Kiwi.com deal was found by Cheapflights users on 11/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/56:09 pmMKE - SJU
1 stop28h 07mMultiple Airlines
Wed 12/105:00 pmSJU - MKE
1 stop18h 39mMultiple Airlines
Deal found 11/29$332
This Kiwi.com deal was found by Cheapflights users on 11/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/810:34 amMKE - SJU
1 stop14h 16mMultiple Airlines
Sun 12/1411:05 amSJU - MKE
1 stop24h 34mMultiple Airlines
Deal found 11/28$338
This Kiwi.com deal was found by Cheapflights users on 11/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/76:09 pmMKE - SJU
1 stop13h 46mMultiple Airlines
Wed 12/175:00 pmSJU - MKE
1 stop28h 20mMultiple Airlines
Deal found 11/28$340
This Expedia deal was found by Cheapflights users on 11/26. 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.
Mon 12/1510:34 amMKE - SJU
1 stop11h 42mMultiple Airlines
Thu 12/255:09 pmSJU - MKE
1 stop26h 12mMultiple Airlines
Deal found 11/26$341
This Kiwi.com deal was found by Cheapflights users on 11/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/810:34 amMKE - SJU
1 stop14h 16mMultiple Airlines
Wed 12/103:55 amSJU - MKE
1 stop7h 44mMultiple Airlines
Deal found 11/28$342
This Delta deal was found by Cheapflights users on 11/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/215:40 amMKE - PLS
1 stop6h 05mDelta
Wed 12/313:50 pmPLS - MKE
1 stop7h 53mDelta
Deal found 11/28$355
This Delta deal was found by Cheapflights users on 11/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/215:40 amMKE - PLS
1 stop7h 45mDelta
Thu 12/252:10 pmPLS - MKE
1 stop9h 33mDelta
Deal found 11/28$356

Cheap flight deals from Milwaukee to Caribbean

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

Round-trip from

$308
(American Airlines)

One-way from

$90
(Frontier)

Popular in

June

Cheapest in

September

Average price

$513

Good round-trip deal

$607 or less

Good one-way deal

$324 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. 8% potential increase in price ($42 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($11 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
Search Deals
Price to beat on a round-trip flight from Milwaukee-Mitchell to Caribbean.
Search Deals
Price to beat on a one-way 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 November 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

Wed 2/25

1:35 pm-11:58 pm

1 stop8h 23m

San Juan Luis Munoz Marin Intl

Thu 3/5

2:16 pm-8:36 pm

1 stop8h 20m

$313

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Wed 2/25

1:35 pm-11:58 pm

1 stop8h 23m

San Juan Luis Munoz Marin Intl

Tue 3/3

6:15 am-12:31 pm

1 stop8h 16m

$313

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Wed 2/25

1:35 pm-11:58 pm

1 stop8h 23m

San Juan Luis Munoz Marin Intl

Wed 3/4

6:15 am-12:31 pm

1 stop8h 16m

$314

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Tue 2/3

11:30 am-12:36 am

2 stops11h 06m

San Juan Luis Munoz Marin Intl

Mon 2/9

2:05 am-10:46 am

1 stop10h 41m

$325

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Sun 2/22

9:44 am-10:22 pm

2 stops10h 38m

San Juan Luis Munoz Marin Intl

Thu 2/26

4:52 pm-10:28 pm

1 stop7h 36m

$325

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Tue 2/24

9:44 am-10:22 pm

2 stops10h 38m

San Juan Luis Munoz Marin Intl

Tue 3/3

2:05 am-2:05 pm

2 stops14h 00m

$325

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Wed 2/25

9:44 am-12:36 am

2 stops12h 52m

San Juan Luis Munoz Marin Intl

Thu 3/5

2:05 am-2:10 pm

2 stops14h 05m

$325

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Wed 2/25

6:00 am-9:26 pm

2 stops13h 26m

San Juan Luis Munoz Marin Intl

Wed 3/4

8:35 am-3:35 pm

1 stop9h 00m

$325

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Wed 2/25

6:00 am-9:26 pm

2 stops13h 26m

San Juan Luis Munoz Marin Intl

Mon 3/2

2:05 am-3:35 pm

2 stops15h 30m

$325

MilwaukeeProvidenciales

MKE - PLS

MKEPLS

Milwaukee-Mitchell

Sun 12/21

5:49 pm-12:00 pm

2 stops17h 11m

Providenciales

Wed 12/31

3:50 pm-10:43 pm

1 stop7h 53m

$355

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/27

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, January is the cheapest month in which you can book a flight from Milwaukee to Caribbean (average of $127). Flying from Milwaukee to Caribbean in December is currently the most expensive (average of $192). 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 November 29, 2025.

It’s typically best to fly out from Milwaukee to Caribbean at noon. Doing so could potentially save you 41% on the flight price compared to flying in the morning, which is usually more expensive.

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

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

Travelers seeking maximum savings on their Milwaukee to Caribbean 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

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 November 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
4,255 reviews

Entertainment

7.5

Crew

8.6

Overall

8.0

Comfort

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.
Southwest
8.0
Very good
4,255 reviews
Southwest
8.0
Very good
4,255 reviews

Entertainment

7.5

Crew

8.6

Overall

8.0

Comfort

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.
Delta
7.9
Good
8,011 reviews
Southwest
8.0
Very good
4,255 reviews

Entertainment

7.5

Crew

8.6

Overall

8.0

Comfort

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.
United Airlines
7.4
Good
9,056 reviews
Southwest
8.0
Very good
4,255 reviews

Entertainment

7.5

Crew

8.6

Overall

8.0

Comfort

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.
American Airlines
7.2
Good
11,043 reviews
Southwest
8.0
Very good
4,255 reviews

Entertainment

7.5

Crew

8.6

Overall

8.0

Comfort

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.
Sun Country Air
6.9
Okay
333 reviews
Southwest
8.0
Very good
4,255 reviews

Entertainment

7.5

Crew

8.6

Overall

8.0

Comfort

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.

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 8h 23m. Delta provides one of the quickest options available for as low as $313. 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 $90 on Frontier. Other airlines that offer cheap prices include Spirit Airlines from $163 and United Airlines from $169 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, January is the cheapest month in which you can book a flight from Milwaukee to Caribbean (average of $127). Flying from Milwaukee to Caribbean in December is currently the most expensive (average of $192). 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 November 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$129Average$229FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$215Average$561FlexibilityNo cancel feeOn-time69%
DeltaCheapest$215Average$589FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$226Average$409FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$274Average$683FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$315Average$765FlexibilityNo cancel feeOn-time63%
Sun Country AirCheapest$540Average$643FlexibilityNo cancel feeOn-time83%

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