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$69+ 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 1/11. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SJU
Dec 14 — Dec 211
Sun 12/14
Sun 12/21
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 14, 2025.

This American Airlines deal was found by Cheapflights users on 11/12. 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 12/94:30 pmMKE - SJU
2 stops15h 39mAmerican Airlines
Tue 12/1612:49 pmSJU - MKE
2 stops12h 12mAmerican Airlines
Deal found 11/12$235
This Kiwi.com deal was found by Cheapflights users on 11/12. 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.
Thu 12/1110:34 amMKE - SJU
1 stop14h 16mMultiple Airlines
Sun 12/213:55 amSJU - MKE
1 stop9h 18mMultiple Airlines
Deal found 11/12$260
This Kiwi.com deal was found by Cheapflights users on 11/11. 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.
Thu 12/1110:34 amMKE - SJU
1 stop14h 16mMultiple Airlines
Thu 12/189:37 pmSJU - MKE
1 stop22h 49mMultiple Airlines
Deal found 11/11$300
This Delta deal was found by Cheapflights users on 11/12. 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 12/97:00 amMKE - SJU
1 stop8h 20mDelta
Tue 12/167:00 amSJU - MKE
1 stop9h 21mDelta
Deal found 11/12$306
This American Airlines deal was found by Cheapflights users on 11/12. 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 12/76:50 pmMKE - SJU
2 stops13h 19mAmerican Airlines
Fri 12/122:36 pmSJU - MKE
2 stops10h 25mAmerican Airlines
Deal found 11/12$308
This Cheapflightsfares deal was found by Cheapflights users on 11/12. 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.
Mon 12/1510:34 amMKE - SJU
1 stop11h 42mSpirit Airlines
Fri 12/1911:38 amSJU - MKE
1 stop9h 42mSpirit Airlines
Deal found 11/12$316
This American Airlines deal was found by Cheapflights users on 11/11. 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.
Mon 11/245:00 amMKE - SJU
1 stop7h 49mAmerican Airlines
Sat 12/68:18 amSJU - MKE
2 stops10h 58mAmerican Airlines
Deal found 11/11$317
This American Airlines deal was found by Cheapflights users on 11/14. 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.
Fri 11/286:00 amMKE - SJU
2 stops12h 58mAmerican Airlines
Sat 12/68:18 amSJU - MKE
2 stops10h 58mAmerican Airlines
Deal found 11/14$324
This United Airlines deal was found by Cheapflights users on 11/12. 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 12/96:00 amMKE - SJU
2 stops13h 26mUnited Airlines
Mon 12/152:05 amSJU - MKE
1 stop10h 39mUnited Airlines
Deal found 11/12$325
This Kiwi.com deal was found by Cheapflights users on 11/13. 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.
Tue 12/308:15 pmMKE - STT
1 stop16h 13mMultiple Airlines
Wed 1/73:23 pmSTT - MKE
1 stop29h 22mMultiple Airlines
Deal found 11/13$332
This Kiwi.com deal was found by Cheapflights users on 11/13. 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.
Tue 12/308:15 pmMKE - STT
1 stop16h 13mMultiple Airlines
Thu 1/83:57 pmSTT - MKE
1 stop29h 04mMultiple Airlines
Deal found 11/13$360
This Delta deal was found by Cheapflights users on 11/12. 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 12/95:45 amMKE - PUJ
1 stop7h 54mDelta
Sun 12/211:53 pmPUJ - MKE
1 stop8h 42mDelta
Deal found 11/12$362

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 14, 2025.

Round-trip from

$235
(United Airlines)

One-way from

$69
(Frontier)

Popular in

June

Cheapest in

September

Average price

$506

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. 9% potential increase in price ($45 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

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 14, 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

Mon 1/19

11:30 am-9:00 pm

1 stop7h 30m

San Juan Luis Munoz Marin Intl

Thu 1/22

2:05 am-12:09 pm

2 stops12h 04m

$235

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Thu 1/29

6:50 am-8:55 pm

1 stop12h 05m

San Juan Luis Munoz Marin Intl

Mon 2/2

5:40 am-1:00 pm

1 stop9h 20m

$235

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Tue 1/20

11:30 am-9:00 pm

1 stop7h 30m

San Juan Luis Munoz Marin Intl

Mon 1/26

2:05 am-1:53 pm

2 stops13h 48m

$269

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Sat 1/24

2:05 pm-11:00 pm

1 stop6h 55m

San Juan Luis Munoz Marin Intl

Sun 2/1

5:35 am-3:35 pm

1 stop12h 00m

$305

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Thu 1/8

11:30 am-9:00 pm

1 stop7h 30m

San Juan Luis Munoz Marin Intl

Wed 1/14

2:05 am-10:46 am

1 stop10h 41m

$316

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Sun 1/11

10:14 am-11:44 pm

1 stop11h 30m

San Juan Luis Munoz Marin Intl

Wed 1/14

6:27 pm-11:30 pm

1 stop7h 03m

$317

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Sun 1/11

3:20 pm-6:11 am

2 stops12h 51m

San Juan Luis Munoz Marin Intl

Wed 1/14

8:35 am-1:53 pm

1 stop7h 18m

$325

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Sat 1/31

2:32 pm-6:11 am

2 stops13h 39m

San Juan Luis Munoz Marin Intl

Fri 2/6

2:05 am-10:15 am

1 stop10h 10m

$325

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Tue 2/3

5:00 am-3:40 pm

1 stop8h 40m

San Juan Luis Munoz Marin Intl

Wed 2/25

2:05 am-3:35 pm

2 stops15h 30m

$325

MilwaukeeSaint Thomas Island

MKE - STT

MKESTT

Milwaukee-Mitchell

Fri 1/2

10:48 am-2:28 pm

2 stops25h 40m

Saint Thomas Island Cyril E King

Wed 1/7

3:23 pm-6:45 pm

1 stop29h 22m

$356

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/12

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 $120). Flying from Milwaukee to Caribbean 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 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 14, 2025.

It’s typically best to fly out from Milwaukee to Caribbean at noon. Doing so could potentially save you 37% 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 14, 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
4,242 reviews

Boarding

8.1

Comfort

8.0

Food

7.0

Overall

8.0

Crew

8.6

Entertainment

7.5

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

Boarding

8.1

Comfort

8.0

Food

7.0

Overall

8.0

Crew

8.6

Entertainment

7.5

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
8,007 reviews
Southwest
8.0
Very good
4,242 reviews

Boarding

8.1

Comfort

8.0

Food

7.0

Overall

8.0

Crew

8.6

Entertainment

7.5

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
9,017 reviews
Southwest
8.0
Very good
4,242 reviews

Boarding

8.1

Comfort

8.0

Food

7.0

Overall

8.0

Crew

8.6

Entertainment

7.5

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
11,051 reviews
Southwest
8.0
Very good
4,242 reviews

Boarding

8.1

Comfort

8.0

Food

7.0

Overall

8.0

Crew

8.6

Entertainment

7.5

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
336 reviews
Southwest
8.0
Very good
4,242 reviews

Boarding

8.1

Comfort

8.0

Food

7.0

Overall

8.0

Crew

8.6

Entertainment

7.5

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. 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 19m. United Airlines provides one of the quickest options available for as low as $362. Airlines will cover a distance of 2032 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • 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 $120). Flying from Milwaukee to Caribbean 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

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 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$129Average$243FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$202Average$560FlexibilityNo cancel feeOn-time69%
DeltaCheapest$215Average$568FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$226Average$407FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$275Average$683FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$315Average$764FlexibilityNo cancel feeOn-time63%
Sun Country AirCheapest$540Average$651FlexibilityNo cancel feeOn-time83%

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