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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 4/26. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SJU
Apr 2 — Apr 91
Wed 4/2
Wed 4/9
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 March 28, 2025.

Round-trip from

$215
(Delta)

One-way from

$108
(American Airlines)

Popular in

December

Cheapest in

September

Average price

$488

Good round-trip deal

$604 or less

Good one-way deal

$292 or less
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. 3% potential price decrease ($15 potential savings vs. average RT price).
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Average for round-trip flights in March 2025
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Price to beat on a round-trip flight from Milwaukee-Mitchell to Caribbean.
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Price to beat on a one-way flight from Milwaukee-Mitchell to Caribbean.
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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 March 28, 2025.

This Delta deal was found by Cheapflights users on 3/27. 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.
Sat 5/31:33 pmMKE - SJU
1 stop8h 42mDelta
Sat 5/106:15 amSJU - MKE
1 stop8h 39mDelta
Deal found 3/27$215
This CheapOair deal was found by Cheapflights users on 3/26. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/275:00 pmMKE - SJU
1 stop14h 26mSpirit Airlines
Sun 5/49:25 amSJU - MKE
1 stop7h 40mSpirit Airlines
Deal found 3/26$229
This United Airlines deal was found by Cheapflights users on 3/26. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/283:43 pmMKE - SJU
1 stop7h 11mUnited Airlines
Thu 5/11:05 amSJU - MKE
1 stop8h 12mUnited Airlines
Deal found 3/26$246
This American Airlines deal was found by Cheapflights users on 3/27. 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.
Sat 5/36:40 amMKE - SJU
1 stop16h 29mAmerican Airlines
Sat 5/101:10 pmSJU - MKE
2 stops9h 17mAmerican Airlines
Deal found 3/27$292
This CheapOair deal was found by Cheapflights users on 3/28. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/114:02 pmMKE - SJU
1 stop20h 14mFrontier
Sat 4/122:45 amSJU - MKE
1 stop17h 18mFrontier
Deal found 3/28$308
This Mytrip deal was found by Cheapflights users on 3/26. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/24:05 pmMKE - PUJ
1 stop21h 37mSpirit Airlines
Wed 4/93:18 pmPUJ - MKE
1 stop25h 47mSpirit Airlines
Deal found 3/26$316
This CheapOair deal was found by Cheapflights users on 3/27. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/41:24 pmMKE - SJU
1 stop10h 18mMultiple Airlines
Thu 4/102:56 amSJU - MKE
1 stop13h 06mMultiple Airlines
Deal found 3/27$320
This Mytrip deal was found by Cheapflights users on 3/27. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/265:06 pmMKE - AUA
2 stops20h 34mSpirit Airlines
Sat 5/33:45 pmAUA - MKE
1 stop25h 20mSpirit Airlines
Deal found 3/27$363
This Mytrip deal was found by Cheapflights users on 3/27. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/215:06 pmMKE - MBJ
2 stops17h 49mSpirit Airlines
Wed 4/3012:00 pmMBJ - MKE
1 stop28h 05mSpirit Airlines
Deal found 3/27$367
This Southwest deal was found by Cheapflights users on 3/27. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/21:25 pmMKE - SJU
1 stop6h 40mSouthwest
Fri 5/96:50 amSJU - MKE
1 stop10h 40mSouthwest
Deal found 3/27$375
This CheapOair deal was found by Cheapflights users on 3/27. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/3012:22 pmMKE - STT
2 stops20h 35mSpirit Airlines
Tue 6/310:52 amSTT - MKE
2 stops25h 35mSpirit Airlines
Deal found 3/27$384
This Mytrip deal was found by Cheapflights users on 3/26. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/125:06 pmMKE - PUJ
1 stop17h 38mMultiple Airlines
Sat 4/1912:39 pmPUJ - MKE
1 stop25h 49mMultiple Airlines
Deal found 3/26$393

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 March 28, 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

Sat 5/3

1:33 pm-11:15 pm

1 stop8h 42m

San Juan Luis Munoz Marin Intl

Sat 5/10

6:15 am-1:54 pm

1 stop8h 39m

$215

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Sun 4/27

5:00 pm-8:26 am

1 stop14h 26m

San Juan Luis Munoz Marin Intl

Sun 5/4

9:25 am-4:05 pm

1 stop7h 40m

$229

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Mon 4/28

3:43 pm-11:54 pm

1 stop7h 11m

San Juan Luis Munoz Marin Intl

Thu 5/1

1:05 am-8:17 am

1 stop8h 12m

$246

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Sat 5/3

6:40 am-12:09 am

1 stop16h 29m

San Juan Luis Munoz Marin Intl

Sat 5/10

1:10 pm-9:27 pm

2 stops9h 17m

$292

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Fri 4/11

4:02 pm-1:16 pm

1 stop20h 14m

San Juan Luis Munoz Marin Intl

Sat 4/12

2:45 am-7:03 pm

1 stop17h 18m

$308

MilwaukeePunta Cana

MKE - PUJ

MKEPUJ

Milwaukee-Mitchell

Wed 4/2

4:05 pm-2:42 pm

1 stop21h 37m

Punta Cana

Wed 4/9

3:18 pm-4:05 pm

1 stop25h 47m

$316

MilwaukeeOranjestad

MKE - AUA

MKEAUA

Milwaukee-Mitchell

Sat 4/26

5:06 pm-2:40 pm

2 stops20h 34m

Oranjestad Reina Beatrix

Sat 5/3

3:45 pm-4:05 pm

1 stop25h 20m

$363

MilwaukeeMontego Bay

MKE - MBJ

MKEMBJ

Milwaukee-Mitchell

Mon 4/21

5:06 pm-10:55 am

2 stops17h 49m

Montego Bay Sangster Intl

Wed 4/30

12:00 pm-4:05 pm

1 stop28h 05m

$367

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Fri 5/2

1:25 pm-9:05 pm

1 stop6h 40m

San Juan Luis Munoz Marin Intl

Fri 5/9

6:50 am-4:30 pm

1 stop10h 40m

$375

MilwaukeeSaint Thomas Island

MKE - STT

MKESTT

Milwaukee-Mitchell

Fri 5/30

12:22 pm-9:57 am

2 stops20h 35m

Saint Thomas Island Cyril E King

Tue 6/3

10:52 am-11:27 am

2 stops25h 35m

$384

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/26

Showing 1-10 of 42 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 December is currently the most expensive (average of $336). 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 March 28, 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.

Rainfall in Caribbean by month

Plan your trip to Caribbean by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Caribbean ranges from 2.2 - 6.1 inches per month. November is typically the wettest month, when rainfall can reach 6.1 in. February is typically the driest time to visit Caribbean when rainfall is around 2.2 in.

Temperature in Caribbean by month

Plan your trip to Caribbean by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Caribbean, use this chart to help with planning. For those seeking warmer temperatures, June is the ideal time of year to visit, when temperatures reach an average of 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 77.0 F).

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 March 28, 2025.
Southwest
8.1
Very good
4,274 reviews

Comfort

8.1

Crew

8.7

Food

7.1

Boarding

8.2

Entertainment

7.6

Overall

8.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Southwest
8.1
Very good
4,274 reviews
Southwest
8.1
Very good
4,274 reviews

Comfort

8.1

Crew

8.7

Food

7.1

Boarding

8.2

Entertainment

7.6

Overall

8.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Alaska Airlines
8.0
Very good
9,798 reviews
Southwest
8.1
Very good
4,274 reviews

Comfort

8.1

Crew

8.7

Food

7.1

Boarding

8.2

Entertainment

7.6

Overall

8.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Delta
8.0
Very good
7,897 reviews
Southwest
8.1
Very good
4,274 reviews

Comfort

8.1

Crew

8.7

Food

7.1

Boarding

8.2

Entertainment

7.6

Overall

8.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
United Airlines
7.4
Good
8,603 reviews
Southwest
8.1
Very good
4,274 reviews

Comfort

8.1

Crew

8.7

Food

7.1

Boarding

8.2

Entertainment

7.6

Overall

8.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
JetBlue
7.3
Good
2,923 reviews
Southwest
8.1
Very good
4,274 reviews

Comfort

8.1

Crew

8.7

Food

7.1

Boarding

8.2

Entertainment

7.6

Overall

8.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

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 American Airlines. Other airlines that offer cheap prices include Spirit Airlines from $125 and Frontier from $148 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 - Oranjestad Reina Beatrix.

  • 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 December is currently the most expensive (average of $336). 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 8 airlines flying from Milwaukee to Caribbean

Discover the top 8 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 March 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$129Average$247FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$155Average$441FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$265Average$678FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$268Average$560FlexibilityNo cancel feeOn-time69%
DeltaCheapest$295Average$536FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$379Average$767FlexibilityNo cancel feeOn-time63%
JetBlueCheapest$384Average$458FlexibilityNo cancel feeOn-time62%
Sun Country AirCheapest$495Average$646FlexibilityNo cancel feeOn-time83%
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