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$83+ 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 1/27. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SJU
Jan 26 — Feb 21
Sun 1/26
Sun 2/2
1 adult, Economy
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Cheap flight deals from Milwaukee to Caribbean

Discover tips and strategies to find the most affordable flight options for your journey from Milwaukee (MKE) to Caribbean (0CB). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated January 21, 2025.

Round-trip from

$155
(FlightHub)

One-way from

$83
(Cheapflightsfares)
From Milwaukee-Mitchell to Caribbean
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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 January 21, 2025.

This FlightHub deal was found by Cheapflights users on 1/20. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/246:47 pmMKE - STT
1 stop13h 59mSpirit Airlines
Thu 2/2711:41 amSTT - MKE
1 stop8h 11mSpirit Airlines
Deal found 1/20$155
This CheapOair deal was found by Cheapflights users on 1/20. 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.
Tue 3/42:14 pmMKE - SJU
1 stop17h 35mFrontier
Tue 3/119:35 pmSJU - MKE
1 stop15h 44mFrontier
Deal found 1/20$220
This Mytrip deal was found by Cheapflights users on 1/20. 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.
Sun 2/25:28 pmMKE - SJU
1 stop13h 53mSpirit Airlines
Wed 2/54:53 pmSJU - MKE
2 stops25h 30mSpirit Airlines
Deal found 1/20$233
This CheapOair deal was found by Cheapflights users on 1/20. 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.
Mon 2/172:14 pmMKE - SJU
1 stop17h 35mMultiple Airlines
Fri 3/76:45 pmSJU - MKE
1 stop24h 00mMultiple Airlines
Deal found 1/20$239
This United Airlines deal was found by Cheapflights users on 1/20. 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 5/311:25 amMKE - SJU
2 stops11h 32mUnited Airlines
Sat 5/101:25 pmSJU - MKE
2 stops9h 50mUnited Airlines
Deal found 1/20$275
This American Airlines deal was found by Cheapflights users on 1/20. 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 2/166:19 pmMKE - SJU
1 stop15h 30mAmerican Airlines
Thu 2/202:40 pmSJU - MKE
1 stop10h 00mAmerican Airlines
Deal found 1/20$300
This Kiwi.com deal was found by Cheapflights users on 1/19. 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 2/246:47 pmMKE - MBJ
1 stop17h 56mSpirit Airlines
Tue 3/42:48 pmMBJ - MKE
1 stop26h 57mSpirit Airlines
Deal found 1/19$313
This Delta deal was found by Cheapflights users on 1/20. 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 2/1812:38 pmMKE - SJU
1 stop6h 28mDelta
Tue 3/46:15 amSJU - MKE
1 stop12h 00mDelta
Deal found 1/20$325
This Kiwi.com deal was found by Cheapflights users on 1/19. 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 2/252:14 pmMKE - MBJ
2 stops22h 29mMultiple Airlines
Tue 3/42:48 pmMBJ - MKE
1 stop26h 57mMultiple Airlines
Deal found 1/19$343
This Kiwi.com deal was found by Cheapflights users on 1/19. 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 2/25:28 pmMKE - PUJ
1 stop20h 17mSpirit Airlines
Thu 2/64:50 pmPUJ - MKE
1 stop25h 33mSpirit Airlines
Deal found 1/19$354
This Kiwi.com deal was found by Cheapflights users on 1/19. 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 2/26:52 pmMKE - PUJ
2 stops17h 25mMultiple Airlines
Thu 2/64:50 pmPUJ - MKE
1 stop25h 33mMultiple Airlines
Deal found 1/19$392
This Kiwi.com deal was found by Cheapflights users on 1/20. 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 3/105:40 pmMKE - NAS
1 stop20h 05mMultiple Airlines
Tue 3/184:00 pmNAS - MKE
1 stop27h 38mMultiple Airlines
Deal found 1/20$395

Find flights from Milwaukee to Caribbean within your budget

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 January 21, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

MilwaukeeSaint Thomas Island

MKE - STT

MKESTT

Milwaukee-Mitchell

Mon 2/24

6:47 pm-10:46 am

1 stop13h 59m

Saint Thomas Island Cyril E King

Thu 2/27

11:41 am-5:52 pm

1 stop8h 11m

$155

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Tue 3/4

2:14 pm-9:49 am

1 stop17h 35m

San Juan Luis Munoz Marin Intl

Tue 3/11

9:35 pm-12:19 pm

1 stop15h 44m

$220

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Mon 3/3

6:47 pm-3:07 pm

2 stops42h 20m

San Juan Luis Munoz Marin Intl

Mon 3/10

7:37 pm-12:19 pm

1 stop17h 42m

$222

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Sun 2/2

5:28 pm-9:21 am

1 stop13h 53m

San Juan Luis Munoz Marin Intl

Wed 2/5

4:53 pm-4:23 pm

2 stops25h 30m

$233

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Sat 5/3

11:25 am-11:57 pm

2 stops11h 32m

San Juan Luis Munoz Marin Intl

Sat 5/10

7:45 am-3:10 pm

1 stop8h 25m

$275

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Sun 2/16

6:19 pm-11:49 am

1 stop15h 30m

San Juan Luis Munoz Marin Intl

Thu 2/20

8:15 am-6:29 pm

2 stops12h 14m

$300

MilwaukeeMontego Bay

MKE - MBJ

MKEMBJ

Milwaukee-Mitchell

Mon 2/24

6:47 pm-1:43 pm

1 stop17h 56m

Montego Bay Sangster Intl

Tue 3/4

2:48 pm-4:45 pm

1 stop26h 57m

$313

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Sat 2/22

3:00 pm-11:46 pm

1 stop6h 46m

San Juan Luis Munoz Marin Intl

Wed 3/5

6:15 am-11:30 am

1 stop7h 15m

$325

MilwaukeeMontego Bay

MKE - MBJ

MKEMBJ

Milwaukee-Mitchell

Tue 2/25

2:14 pm-1:43 pm

2 stops22h 29m

Montego Bay Sangster Intl

Tue 3/4

2:48 pm-4:45 pm

1 stop26h 57m

$343

MilwaukeePunta Cana

MKE - PUJ

MKEPUJ

Milwaukee-Mitchell

Sun 2/2

5:28 pm-3:45 pm

1 stop20h 17m

Punta Cana

Thu 2/6

4:50 pm-4:23 pm

1 stop25h 33m

$354

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/20

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.

Travel insights for flights from Milwaukee to Caribbean

Get recent, data-driven insights about flights from Milwaukee to Caribbean including ideal travel times, pricing trends, and more.

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 March is currently the most expensive (average of $378). 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 January 21, 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 January 21, 2025.
Southwest
8.1
Very good
4,659 reviews

Overall

8.1

Boarding

8.2

Crew

8.7

Comfort

8.1

Entertainment

7.7

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,659 reviews
Southwest
8.1
Very good
4,659 reviews

Overall

8.1

Boarding

8.2

Crew

8.7

Comfort

8.1

Entertainment

7.7

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Alaska Airlines
8.0
Very good
9,706 reviews
Southwest
8.1
Very good
4,659 reviews

Overall

8.1

Boarding

8.2

Crew

8.7

Comfort

8.1

Entertainment

7.7

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,521 reviews
Southwest
8.1
Very good
4,659 reviews

Overall

8.1

Boarding

8.2

Crew

8.7

Comfort

8.1

Entertainment

7.7

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

United Airlines
7.4
Good
8,982 reviews
Southwest
8.1
Very good
4,659 reviews

Overall

8.1

Boarding

8.2

Crew

8.7

Comfort

8.1

Entertainment

7.7

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

American Airlines
7.2
Good
10,000 reviews
Southwest
8.1
Very good
4,659 reviews

Overall

8.1

Boarding

8.2

Crew

8.7

Comfort

8.1

Entertainment

7.7

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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 $83 on Spirit Airlines. Other airlines that offer cheap prices include Frontier from $85 and American Airlines from $138 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 March is currently the most expensive (average of $378). 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 January 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$138Average$376FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$167Average$414FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$261Average$616FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$274Average$557FlexibilityNo cancel feeOn-time69%
DeltaCheapest$324Average$529FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$360Average$569FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$379Average$740FlexibilityNo cancel feeOn-time63%
Sun Country AirCheapest$498Average$669FlexibilityNo cancel feeOn-time83%
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