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$108+ 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 9/23. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SJU
Aug 22 — Aug 291
Fri 8/22
Fri 8/29
1 adult, Economy
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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 August 17, 2025.

Round-trip from

$215
(American Airlines)

One-way from

$108
(Southwest)

Popular in

June

Cheapest in

September

Average price

$399
From Milwaukee-Mitchell to Caribbean
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One-way flight from Milwaukee-Mitchell to Caribbean
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Highest demand for flights based on searches. 9% potential increase in price ($47 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($12 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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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 August 17, 2025.

This American Airlines deal was found by Cheapflights users on 8/16. 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.
Sat 10/2511:33 amMKE - SJU
2 stops11h 21mAmerican Airlines
Thu 10/307:45 amSJU - MKE
1 stop16h 31mAmerican Airlines
Deal found 8/16$215
This American Airlines deal was found by Cheapflights users on 8/17. 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.
Wed 9/243:47 pmMKE - SJU
2 stops18h 24mAmerican Airlines
Mon 9/294:43 pmSJU - MKE
2 stops18h 21mAmerican Airlines
Deal found 8/17$221
This American Airlines deal was found by Cheapflights users on 8/17. 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 9/216:00 amMKE - SJU
2 stops16h 37mAmerican Airlines
Wed 9/244:43 pmSJU - MKE
2 stops18h 49mAmerican Airlines
Deal found 8/17$245
This American Airlines deal was found by Cheapflights users on 8/16. 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.
Sat 10/111:20 pmMKE - SJU
1 stop8h 45mAmerican Airlines
Sat 10/187:10 amSJU - MKE
2 stops13h 36mAmerican Airlines
Deal found 8/16$270
This American Airlines deal was found by Cheapflights users on 8/16. 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.
Sat 11/158:05 amMKE - SJU
2 stops11h 27mAmerican Airlines
Tue 11/185:59 pmSJU - MKE
1 stop6h 57mAmerican Airlines
Deal found 8/16$275
This Southwest deal was found by Cheapflights users on 8/17. 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 9/243:00 pmMKE - SJU
1 stop6h 45mSouthwest
Mon 9/295:50 amSJU - MKE
1 stop10h 55mSouthwest
Deal found 8/17$297
This American Airlines deal was found by Cheapflights users on 8/17. 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 9/1911:25 amMKE - SJU
2 stops11h 12mAmerican Airlines
Tue 9/236:10 amSJU - MKE
2 stops18h 33mAmerican Airlines
Deal found 8/17$305
This American Airlines deal was found by Cheapflights users on 8/16. 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 9/296:23 pmMKE - SJU
2 stops17h 24mAmerican Airlines
Mon 10/611:56 amSJU - MKE
2 stops13h 18mAmerican Airlines
Deal found 8/16$313
This Southwest deal was found by Cheapflights users on 8/17. 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 9/1912:20 pmMKE - SJU
1 stop10h 10mSouthwest
Tue 9/233:05 pmSJU - MKE
1 stop7h 45mSouthwest
Deal found 8/17$315
This American Airlines deal was found by Cheapflights users on 8/16. 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.
Sat 10/111:20 pmMKE - SJU
1 stop8h 45mAmerican Airlines
Sun 10/197:10 amSJU - MKE
1 stop18h 04mAmerican Airlines
Deal found 8/16$330
This Delta deal was found by Cheapflights users on 8/16. 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 9/2110:29 amMKE - SJU
1 stop10h 31mDelta
Sat 9/277:30 amSJU - MKE
1 stop10h 05mDelta
Deal found 8/16$333
This United Airlines deal was found by Cheapflights users on 8/16. 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 9/96:00 amMKE - PUJ
1 stop8h 25mUnited Airlines
Thu 9/113:15 pmPUJ - MKE
1 stop9h 14mUnited Airlines
Deal found 8/16$351

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 August 17, 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

Fri 10/24

1:43 pm-11:59 pm

1 stop9h 16m

San Juan Luis Munoz Marin Intl

Thu 10/30

7:45 am-11:16 pm

1 stop16h 31m

$215

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Sat 11/15

10:25 am-11:17 pm

1 stop10h 52m

San Juan Luis Munoz Marin Intl

Tue 11/18

6:20 pm-11:25 pm

1 stop7h 05m

$215

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Sat 1/24

11:47 am-11:40 pm

1 stop9h 53m

San Juan Luis Munoz Marin Intl

Fri 1/30

2:25 pm-9:25 pm

1 stop9h 00m

$215

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Sat 10/11

6:00 am-2:11 pm

1 stop7h 11m

San Juan Luis Munoz Marin Intl

Sat 10/18

5:43 pm-11:55 pm

1 stop7h 12m

$215

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Wed 10/15

6:00 am-11:59 pm

1 stop16h 59m

San Juan Luis Munoz Marin Intl

Thu 10/23

7:10 am-12:14 am

1 stop18h 04m

$215

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Sat 10/25

11:33 am-11:54 pm

2 stops11h 21m

San Juan Luis Munoz Marin Intl

Thu 10/30

7:45 am-11:16 pm

1 stop16h 31m

$215

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Tue 9/16

8:00 am-3:52 pm

1 stop6h 52m

San Juan Luis Munoz Marin Intl

Tue 9/23

6:10 am-11:43 pm

2 stops18h 33m

$215

MilwaukeePunta Cana

MKE - PUJ

MKEPUJ

Milwaukee-Mitchell

Tue 9/9

6:00 am-3:25 pm

1 stop8h 25m

Punta Cana

Thu 9/11

3:15 pm-11:29 pm

1 stop9h 14m

$351

MilwaukeePunta Cana

MKE - PUJ

MKEPUJ

Milwaukee-Mitchell

Tue 10/21

5:26 am-3:29 pm

2 stops9h 03m

Punta Cana

Tue 10/28

4:39 pm-11:50 am

2 stops20h 11m

$355

MilwaukeeProvidenciales

MKE - PLS

MKEPLS

Milwaukee-Mitchell

Tue 9/30

5:40 am-12:45 pm

1 stop6h 05m

Providenciales

Tue 10/7

2:05 pm-8:42 pm

1 stop7h 37m

$360

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/16

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, September is the cheapest month in which you can book a flight from Milwaukee to Caribbean (average of $254). Flying from Milwaukee to Caribbean in June is currently the most expensive (average of $339). 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 August 17, 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 August 17, 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
4,246 reviews

Crew

8.6

Food

7.0

Overall

8.0

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Southwest
8.0
Very good
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Crew

8.6

Food

7.0

Overall

8.0

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Delta
8.0
Very good
7,986 reviews
Southwest
8.0
Very good
4,246 reviews

Crew

8.6

Food

7.0

Overall

8.0

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
United Airlines
7.4
Good
8,919 reviews
Southwest
8.0
Very good
4,246 reviews

Crew

8.6

Food

7.0

Overall

8.0

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,246 reviews

Crew

8.6

Food

7.0

Overall

8.0

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Sun Country Air
6.9
Okay
333 reviews
Southwest
8.0
Very good
4,246 reviews

Crew

8.6

Food

7.0

Overall

8.0

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.

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.

  • 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 $108 on Delta. Other airlines that offer cheap prices include American Airlines from $110 and Spirit Airlines from $188 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, September is the cheapest month in which you can book a flight from Milwaukee to Caribbean (average of $254). Flying from Milwaukee to Caribbean in June is currently the most expensive (average of $339). 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 August 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$129Average$233FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$202Average$597FlexibilityNo cancel feeOn-time69%
Spirit AirlinesCheapest$208Average$391FlexibilityNo cancel feeOn-time65%
DeltaCheapest$223Average$575FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$275Average$684FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$322Average$746FlexibilityNo cancel feeOn-time63%
Sun Country AirCheapest$502Average$649FlexibilityNo cancel feeOn-time83%

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