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$118+ 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 11/9. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SJU
Nov 13 — Nov 201
Thu 11/13
Thu 11/20
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 October 14, 2025.

This Delta deal was found by Cheapflights users on 10/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/711:39 amMKE - SJU
1 stop9h 41mDelta
Wed 12/107:00 amSJU - MKE
1 stop9h 21mDelta
Deal found 10/14$235
This United Airlines deal was found by Cheapflights users on 10/12. 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.
Sat 11/88:44 amMKE - SJU
2 stops10h 42mUnited Airlines
Sat 11/158:30 amSJU - MKE
2 stops10h 02mUnited Airlines
Deal found 10/12$253
This Southwest deal was found by Cheapflights users on 10/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/1212:45 pmMKE - SJU
1 stop7h 15mSouthwest
Thu 12/186:10 amSJU - MKE
1 stop12h 05mSouthwest
Deal found 10/13$274
This Southwest deal was found by Cheapflights users on 10/12. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/35:30 amMKE - SJU
2 stops11h 05mSouthwest
Wed 2/410:20 amSJU - MKE
1 stop7h 00mSouthwest
Deal found 10/12$305
This American Airlines deal was found by Cheapflights users on 10/14. 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.
Tue 11/45:00 amMKE - SJU
2 stops13h 48mAmerican Airlines
Sat 11/87:15 amSJU - MKE
1 stop16h 20mAmerican Airlines
Deal found 10/14$308
This Frontier deal was found by Cheapflights users on 10/14. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/57:48 pmMKE - SJU
1 stop12h 07mFrontier
Fri 12/1211:05 amSJU - MKE
1 stop9h 48mFrontier
Deal found 10/14$312
This Southwest deal was found by Cheapflights users on 10/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/35:30 amMKE - SJU
2 stops11h 05mSouthwest
Tue 2/35:40 amSJU - MKE
2 stops14h 45mSouthwest
Deal found 10/13$313
This Delta deal was found by Cheapflights users on 10/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/16:00 amMKE - SJU
1 stop7h 11mDelta
Thu 11/66:43 pmSJU - MKE
1 stop7h 12mDelta
Deal found 10/14$317
This United Airlines deal was found by Cheapflights users on 10/14. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/98:40 amMKE - SJU
2 stops11h 42mUnited Airlines
Wed 12/108:30 amSJU - MKE
2 stops15h 17mUnited Airlines
Deal found 10/14$320
This American Airlines deal was found by Cheapflights users on 10/14. 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.
Mon 11/36:00 amMKE - SJU
2 stops12h 48mAmerican Airlines
Thu 11/62:05 pmSJU - MKE
1 stop11h 57mAmerican Airlines
Deal found 10/14$322
This United Airlines deal was found by Cheapflights users on 10/13. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/68:40 amMKE - SJU
2 stops11h 42mUnited Airlines
Fri 12/122:05 amSJU - MKE
1 stop10h 39mUnited Airlines
Deal found 10/13$323
This United Airlines deal was found by Cheapflights users on 10/13. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/158:00 amMKE - SJU
1 stop11h 26mUnited Airlines
Mon 11/172:05 amSJU - MKE
2 stops11h 24mUnited Airlines
Deal found 10/13$325

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 October 14, 2025.

Round-trip from

$235
(Delta)

One-way from

$118
(American Airlines)

Popular in

June

Cheapest in

September

Average price

$338

Good round-trip deal

$767 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. 10% potential increase in price ($50 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 October 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 October 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

Sun 12/7

11:39 am-11:20 pm

1 stop9h 41m

San Juan Luis Munoz Marin Intl

Tue 12/9

2:08 pm-8:22 pm

1 stop8h 14m

$235

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Wed 2/25

11:30 am-12:36 am

2 stops11h 06m

San Juan Luis Munoz Marin Intl

Wed 3/11

7:35 am-2:05 pm

1 stop7h 30m

$308

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Sat 12/6

7:05 am-5:20 pm

1 stop8h 15m

San Juan Luis Munoz Marin Intl

Wed 12/10

7:00 am-4:16 pm

1 stop11h 16m

$317

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Wed 12/10

7:00 am-5:20 pm

1 stop8h 20m

San Juan Luis Munoz Marin Intl

Fri 12/12

7:00 am-2:21 pm

1 stop9h 21m

$317

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Tue 12/9

7:00 am-5:20 pm

1 stop8h 20m

San Juan Luis Munoz Marin Intl

Fri 12/12

7:00 am-4:13 pm

1 stop11h 13m

$317

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Wed 12/10

7:00 am-5:20 pm

1 stop8h 20m

San Juan Luis Munoz Marin Intl

Thu 12/11

6:38 pm-11:55 pm

1 stop7h 17m

$317

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Thu 12/4

11:30 am-9:30 pm

1 stop8h 00m

San Juan Luis Munoz Marin Intl

Tue 12/9

11:20 am-9:25 pm

1 stop12h 05m

$325

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Tue 12/9

8:40 am-10:22 pm

2 stops11h 42m

San Juan Luis Munoz Marin Intl

Fri 12/12

8:10 am-3:08 pm

1 stop8h 58m

$325

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Sat 11/15

6:05 am-9:26 pm

2 stops13h 21m

San Juan Luis Munoz Marin Intl

Mon 11/17

2:05 am-1:58 pm

2 stops13h 53m

$325

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Sat 1/31

3:20 pm-6:11 am

2 stops12h 51m

San Juan Luis Munoz Marin Intl

Mon 2/9

2:05 am-3:43 pm

2 stops15h 38m

$325

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/13

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, February 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 $186). 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 October 14, 2025.

It’s typically best to fly out from Milwaukee to Caribbean at noon. Doing so could potentially save you 36% 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 October 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
4,238 reviews

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

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

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

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
8.0
Very good
7,977 reviews
Southwest
8.0
Very good
4,238 reviews

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

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
8,977 reviews
Southwest
8.0
Very good
4,238 reviews

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

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
11,044 reviews
Southwest
8.0
Very good
4,238 reviews

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

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
335 reviews
Southwest
8.0
Very good
4,238 reviews

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

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 9h 41m. Delta 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 $118 on Delta. Other airlines that offer cheap prices include United Airlines from $118 and American Airlines from $118 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, February 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 $186). 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 October 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$129Average$238FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$188Average$561FlexibilityNo cancel feeOn-time69%
DeltaCheapest$215Average$566FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$226Average$392FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$275Average$669FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$315Average$753FlexibilityNo cancel feeOn-time63%
Sun Country AirCheapest$540Average$650FlexibilityNo cancel feeOn-time83%

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