HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Caribbean

$119+ 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 2/7. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SJU
Dec 26 — Jan 21
Thu 12/26
Thu 1/2
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Milwaukee to Caribbean with Cheapflights

1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”
2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.
3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 December 21, 2024.

Round-trip from

$200
(FlightHub)

One-way from

$119
(Mytrip)
From Milwaukee-Mitchell to Caribbean
Search Deals
One-way flight from Milwaukee-Mitchell to Caribbean
Search Deals

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 December 21, 2024.

This Mytrip deal was found by Cheapflights users on 12/20. 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 12/295:00 amMKE - SJU
1 stop13h 22mMultiple Airlines
Mon 1/136:56 pmSJU - MKE
1 stop16h 51mMultiple Airlines
Deal found 12/20$342
This American Airlines deal was found by Cheapflights users on 12/21. 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 12/2211:39 amMKE - SJU
2 stops10h 46mAmerican Airlines
Wed 12/259:00 amSJU - MKE
1 stop10h 20mAmerican Airlines
Deal found 12/21$442
This Delta deal was found by Cheapflights users on 12/20. 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 12/246:30 amMKE - SJU
1 stop7h 20mDelta
Thu 12/266:30 amSJU - MKE
1 stop9h 36mDelta
Deal found 12/20$518
This United deal was found by Cheapflights users on 12/21. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/228:00 amMKE - SJU
1 stop10h 55mUnited Airlines
Tue 12/242:05 amSJU - MKE
1 stop9h 39mUnited Airlines
Deal found 12/21$598
This Delta deal was found by Cheapflights users on 12/21. 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.
Mon 12/306:00 amMKE - PUJ
1 stop8h 52mDelta
Thu 1/94:50 pmPUJ - MKE
1 stop9h 03mDelta
Deal found 12/21$600
This FlightHub deal was found by Cheapflights users on 12/20. 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.
Tue 12/245:00 amMKE - STT
1 stop27h 39mSpirit Airlines
Thu 12/2611:44 amSTT - MKE
1 stop13h 01mSpirit Airlines
Deal found 12/20$609
This CheapOair deal was found by Cheapflights users on 12/20. 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.
Sun 12/295:00 amMKE - SJU
1 stop13h 22mSpirit Airlines
Thu 1/24:30 amSJU - MKE
2 stops20h 15mSpirit Airlines
Deal found 12/20$631
This FlightHub deal was found by Cheapflights users on 12/20. 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.
Tue 12/248:22 pmMKE - SJU
1 stop18h 49mFrontier
Fri 12/273:54 amSJU - MKE
1 stop17h 36mFrontier
Deal found 12/20$651
This Mytrip deal was found by Cheapflights users on 12/21. 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 12/305:00 amMKE - PUJ
1 stop8h 55mMultiple Airlines
Thu 1/94:30 pmPUJ - MKE
2 stops25h 53mMultiple Airlines
Deal found 12/21$665
This Mytrip deal was found by Cheapflights users on 12/21. 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 12/256:55 amMKE - STT
1 stop7h 55mMultiple Airlines
Mon 12/3011:44 amSTT - MKE
1 stop13h 01mMultiple Airlines
Deal found 12/21$679
This United Airlines deal was found by Cheapflights users on 12/20. 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.
Sun 12/295:00 amMKE - GCM
2 stops10h 25mUnited Airlines
Wed 1/12:50 pmGCM - MKE
1 stop8h 40mUnited Airlines
Deal found 12/20$694
This American Airlines deal was found by Cheapflights users on 12/21. 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 12/306:15 pmMKE - PUJ
2 stops17h 51mAmerican Airlines
Thu 1/91:30 pmPUJ - MKE
2 stops10h 22mAmerican Airlines
Deal found 12/21$721

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 December 21, 2024.

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

Tue 3/4

11:41 am-9:30 am

1 stop23h 49m

$200

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Thu 2/27

6:47 pm-11:25 pm

1 stop26h 38m

San Juan Luis Munoz Marin Intl

Tue 3/4

2:45 am-9:07 pm

1 stop20h 22m

$291

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Sat 1/11

10:54 am-2:55 pm

2 stops26h 01m

San Juan Luis Munoz Marin Intl

Thu 1/16

10:09 pm-4:23 pm

1 stop20h 14m

$293

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Thu 2/27

1:22 pm-10:35 pm

1 stop7h 13m

San Juan Luis Munoz Marin Intl

Tue 3/4

7:45 am-5:33 pm

2 stops11h 48m

$294

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Fri 2/14

2:14 pm-9:35 am

1 stop17h 21m

San Juan Luis Munoz Marin Intl

Fri 2/21

10:43 pm-1:14 pm

1 stop16h 31m

$296

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Sat 4/5

2:25 pm-11:54 pm

1 stop8h 29m

San Juan Luis Munoz Marin Intl

Tue 4/8

1:05 am-1:47 pm

2 stops13h 42m

$316

MilwaukeePunta Cana

MKE - PUJ

MKEPUJ

Milwaukee-Mitchell

Sun 2/2

5:28 pm-3:45 pm

1 stop20h 17m

Punta Cana

Sun 2/9

4:50 pm-4:23 pm

1 stop25h 33m

$317

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Mon 2/17

6:00 am-4:27 pm

1 stop8h 27m

San Juan Luis Munoz Marin Intl

Thu 2/27

6:15 am-3:03 pm

1 stop10h 48m

$324

MilwaukeeMontego Bay

MKE - MBJ

MKEMBJ

Milwaukee-Mitchell

Sun 2/23

6:47 pm-1:36 pm

1 stop17h 49m

Montego Bay Sangster Intl

Wed 2/26

2:41 pm-5:52 pm

1 stop28h 11m

$336

MilwaukeeMontego Bay

MKE - MBJ

MKEMBJ

Milwaukee-Mitchell

Fri 1/31

6:52 pm-1:48 pm

1 stop17h 56m

Montego Bay Sangster Intl

Wed 2/5

1:16 pm-4:22 pm

1 stop28h 06m

$361

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/19

Showing 1-10 of 48 results
1
2
3
...
5

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 $380). 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 December 21, 2024.

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 December 21, 2024.
Southwest
8.1
Very good
4,814 reviews

Comfort

8.1

Boarding

8.2

Entertainment

7.7

Overall

8.1

Crew

8.7

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
4,814 reviews
Southwest
8.1
Very good
4,814 reviews

Comfort

8.1

Boarding

8.2

Entertainment

7.7

Overall

8.1

Crew

8.7

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
9,537 reviews
Southwest
8.1
Very good
4,814 reviews

Comfort

8.1

Boarding

8.2

Entertainment

7.7

Overall

8.1

Crew

8.7

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
8,597 reviews
Southwest
8.1
Very good
4,814 reviews

Comfort

8.1

Boarding

8.2

Entertainment

7.7

Overall

8.1

Crew

8.7

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.

LATAM Airlines
7.5
Good
1,873 reviews
Southwest
8.1
Very good
4,814 reviews

Comfort

8.1

Boarding

8.2

Entertainment

7.7

Overall

8.1

Crew

8.7

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
9,039 reviews
Southwest
8.1
Very good
4,814 reviews

Comfort

8.1

Boarding

8.2

Entertainment

7.7

Overall

8.1

Crew

8.7

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 $119 on Spirit Airlines. Other airlines that offer cheap prices include American Airlines from $132 and Frontier from $143 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 $380). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Milwaukee to Caribbean

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Cancún flights
O'Hare Intl to Orlando flights
O'Hare Intl to John F Kennedy Intl flights
O'Hare Intl to Dallas/Fort Worth flights
O'Hare Intl to Sky Harbor Intl flights
O'Hare Intl to Las Vegas flights
O'Hare Intl to LaGuardia flights
O'Hare Intl to Los Angeles flights
O'Hare Intl to Miami flights
Minneapolis to Las Vegas flights
O'Hare Intl to Fort Lauderdale flights
Minneapolis to Cancún flights
O'Hare Intl to Mexico City flights
O'Hare Intl to Newark flights
Minneapolis to Sky Harbor Intl flights
Minneapolis to Orlando flights
Minneapolis to Miami flights
O'Hare Intl to Denver flights
O'Hare Intl to Seattle flights
Minneapolis to Fort Lauderdale flights
O'Hare Intl to Luis Munoz Marin Intl flights
O'Hare Intl to Boston flights
O'Hare Intl to Tampa flights
O'Hare Intl to Hobby flights
O'Hare Intl to Charles de Gaulle flights
Minneapolis to Dallas/Fort Worth flights
O'Hare Intl to Atlanta flights
Minneapolis to Seattle flights
O'Hare Intl to Heathrow flights
O'Hare Intl to New Orleans flights
O'Hare Intl to Honolulu flights
O'Hare Intl to San Francisco flights
O'Hare Intl to San Diego flights
Minneapolis to Fort Myers flights
Minneapolis to Los Angeles flights
O'Hare Intl to Fort Myers flights
O'Hare Intl to George Bush Intcntl flights
Minneapolis to Tampa flights
O'Hare Intl to Leonardo da Vinci/Fiumicino flights
O'Hare Intl to Punta Cana flights
Minneapolis to John F Kennedy Intl flights
O'Hare Intl to Narita flights
Minneapolis to LaGuardia flights
O'Hare Intl to Cozumel flights
O'Hare Intl to West Palm Beach flights
O'Hare Intl to Haneda flights
O'Hare Intl to Suvarnabhumi flights
O'Hare Intl to Dulles Intl flights
O'Hare Intl to Santa Ana flights
O'Hare Intl to Istanbul flights

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 December 21, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$146Average$383FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$168Average$409FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$258Average$598FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$274Average$557FlexibilityNo cancel feeOn-time69%
DeltaCheapest$324Average$549FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$360Average$573FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$379Average$725FlexibilityNo cancel feeOn-time63%
Sun Country AirCheapest$498Average$670FlexibilityNo cancel feeOn-time83%
100% Free
Cheapflights is completely free to use, so you can start saving the moment you arrive.
Book with Flexibility
Our users can plan ahead with confidence and find flights with no change fees
Travel Smart
Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.