HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Caribbean

$127+ 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 2/19. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SJU
nov. 25 — dic. 21
lun. 11/25
lun. 12/2
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 noviembre 20, 2024.

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 noviembre 20, 2024.

This CheapOair deal was found by Cheapflights users on 11/19. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 12/105:00 amMKE - STT
1 stop27h 51mSpirit Airlines
mié. 12/1811:44 amSTT - MKE
1 stop13h 01mSpirit Airlines
Deal found 11/19$219
This CheapOair deal was found by Cheapflights users on 11/19. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 11/268:05 amMKE - SJU
1 stop10h 33mMultiple Airlines
mié. 12/49:15 pmSJU - MKE
1 stop14h 32mMultiple Airlines
Deal found 11/19$273
This CheapOair deal was found by Cheapflights users on 11/19. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 12/610:47 amMKE - SJU
1 stop13h 53mFrontier
sáb. 12/149:49 pmSJU - MKE
1 stop13h 58mFrontier
Deal found 11/19$274
This Mytrip deal was found by Cheapflights users on 11/19. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 12/95:00 amMKE - SJU
2 stops29h 33mSpirit Airlines
mar. 12/178:31 pmSJU - MKE
2 stops28h 14mSpirit Airlines
Deal found 11/19$285
This American Airlines deal was found by Cheapflights users on 11/19. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 12/96:54 amMKE - SJU
1 stop12h 01mAmerican Airlines
mar. 12/175:30 amSJU - MKE
2 stops10h 04mAmerican Airlines
Deal found 11/19$311
This Mytrip deal was found by Cheapflights users on 11/19. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 12/145:00 amMKE - PUJ
2 stops31h 00mSpirit Airlines
mié. 12/184:50 pmPUJ - MKE
1 stop7h 55mSpirit Airlines
Deal found 11/19$316
This Booking.com deal was found by Cheapflights users on 11/19. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 12/145:00 amMKE - MBJ
1 stop7h 33mSpirit Airlines
mié. 12/182:38 pmMBJ - MKE
1 stop9h 07mSpirit Airlines
Deal found 11/19$320
This Kiwi.com deal was found by Cheapflights users on 11/19. 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.
mar. 12/105:00 amMKE - AUA
1 stop8h 40mSpirit Airlines
jue. 12/124:40 pmAUA - MKE
1 stop31h 02mSpirit Airlines
Deal found 11/19$331
This Delta deal was found by Cheapflights users on 11/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 12/107:00 amMKE - SJU
1 stop8h 15mDelta
jue. 12/126:25 pmSJU - MKE
1 stop7h 32mDelta
Deal found 11/19$334
This Mytrip deal was found by Cheapflights users on 11/19. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 12/105:00 amMKE - STT
2 stops30h 23mMultiple Airlines
mié. 12/185:45 pmSTT - MKE
3 stops25h 44mMultiple Airlines
Deal found 11/19$342
This United deal was found by Cheapflights users on 11/19. 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 United is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 12/1011:45 amMKE - SJU
2 stops10h 51mUnited Airlines
vie. 12/132:05 amSJU - MKE
2 stops11h 47mUnited Airlines
Deal found 11/19$354
This Kiwi.com deal was found by Cheapflights users on 11/19. 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.
mar. 12/105:00 amMKE - AUA
1 stop8h 40mMultiple Airlines
jue. 12/124:40 pmAUA - MKE
2 stops19h 07mMultiple Airlines
Deal found 11/19$399

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 2,629,791 searches. Data last updated noviembre 20, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

MilwaukeeSaint Thomas Island

MKE - STT

MKESTT

Milwaukee-Mitchell

mar. 12/10

5:00 am-10:51 am

1 stop27h 51m

Saint Thomas Island Cyril E King

mié. 12/18

11:44 am-10:45 pm

1 stop13h 01m

$219

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

jue. 1/9

5:51 pm-9:35 am

1 stop13h 44m

San Juan Luis Munoz Marin Intl

lun. 1/13

9:49 pm-9:47 am

1 stop13h 58m

$269

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

mar. 1/21

7:59 am-10:07 pm

2 stops12h 08m

San Juan Luis Munoz Marin Intl

jue. 1/30

4:40 pm-9:56 pm

1 stop7h 16m

$274

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

mié. 1/15

10:54 am-7:31 pm

1 stop6h 37m

San Juan Luis Munoz Marin Intl

lun. 1/20

9:49 pm-9:54 am

1 stop14h 05m

$278

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

mar. 12/10

5:00 am-8:22 pm

1 stop13h 22m

San Juan Luis Munoz Marin Intl

dom. 12/15

3:20 am-9:42 pm

2 stops20h 22m

$281

MilwaukeePunta Cana

MKE - PUJ

MKEPUJ

Milwaukee-Mitchell

sáb. 12/14

5:00 am-2:00 pm

2 stops31h 00m

Punta Cana

mié. 12/18

4:50 pm-10:45 pm

1 stop7h 55m

$316

MilwaukeeMontego Bay

MKE - MBJ

MKEMBJ

Milwaukee-Mitchell

sáb. 12/14

5:00 am-1:33 pm

1 stop7h 33m

Montego Bay Sangster Intl

mié. 12/18

2:38 pm-10:45 pm

1 stop9h 07m

$320

MilwaukeeOranjestad

MKE - AUA

MKEAUA

Milwaukee-Mitchell

mar. 12/10

5:00 am-3:40 pm

1 stop8h 40m

Oranjestad Reina Beatrix

jue. 12/12

4:40 pm-9:42 pm

1 stop31h 02m

$331

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

mar. 12/10

1:02 pm-12:59 am

1 stop9h 57m

San Juan Luis Munoz Marin Intl

dom. 12/15

3:25 pm-11:57 pm

1 stop10h 32m

$334

MilwaukeeSaint Thomas Island

MKE - STT

MKESTT

Milwaukee-Mitchell

mar. 12/10

5:00 am-1:23 pm

2 stops30h 23m

Saint Thomas Island Cyril E King

mié. 12/18

5:45 pm-5:29 pm

3 stops25h 44m

$342

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/20

Showing 1-10 of 55 results
1
2
3
...
6

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 $335). 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 noviembre 20, 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 noviembre 20, 2024.
Southwest
8.1
Very good
5,014 reviews

Comfort

8.1

Crew

8.7

Boarding

8.2

Overall

8.1

Food

7.2

Entertainment

7.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Southwest
8.1
Very good
5,014 reviews
Southwest
8.1
Very good
5,014 reviews

Comfort

8.1

Crew

8.7

Boarding

8.2

Overall

8.1

Food

7.2

Entertainment

7.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Delta
8.0
Very good
8,756 reviews
Southwest
8.1
Very good
5,014 reviews

Comfort

8.1

Crew

8.7

Boarding

8.2

Overall

8.1

Food

7.2

Entertainment

7.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

United Airlines
7.4
Good
9,171 reviews
Southwest
8.1
Very good
5,014 reviews

Comfort

8.1

Crew

8.7

Boarding

8.2

Overall

8.1

Food

7.2

Entertainment

7.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

WestJet
7.3
Good
2,811 reviews
Southwest
8.1
Very good
5,014 reviews

Comfort

8.1

Crew

8.7

Boarding

8.2

Overall

8.1

Food

7.2

Entertainment

7.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

American Airlines
7.2
Good
10,000 reviews
Southwest
8.1
Very good
5,014 reviews

Comfort

8.1

Crew

8.7

Boarding

8.2

Overall

8.1

Food

7.2

Entertainment

7.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

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 $127 on Spirit Airlines. Other airlines that offer cheap prices include American Airlines from $137 and Frontier from $149 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 $335). 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 Miami flights
O'Hare Intl to Dallas/Fort Worth flights
O'Hare Intl to John F Kennedy Intl flights
O'Hare Intl to Los Angeles flights
O'Hare Intl to Fort Lauderdale flights
O'Hare Intl to LaGuardia flights
O'Hare Intl to Mexico City flights
O'Hare Intl to Sky Harbor Intl flights
O'Hare Intl to Las Vegas flights
Minneapolis to Las Vegas flights
O'Hare Intl to Newark flights
Minneapolis to Cancún flights
Minneapolis to Sky Harbor Intl flights
Minneapolis to Orlando flights
O'Hare Intl to Tampa flights
O'Hare Intl to Denver flights
O'Hare Intl to Seattle flights
O'Hare Intl to Atlanta flights
Minneapolis to Newark flights
Minneapolis to LaGuardia flights
O'Hare Intl to Heathrow flights
O'Hare Intl to Luis Munoz Marin Intl flights
O'Hare Intl to Hobby flights
O'Hare Intl to Boston flights
O'Hare Intl to Cozumel flights
O'Hare Intl to Charles de Gaulle flights
Minneapolis to Fort Myers flights
Minneapolis to Seattle flights
O'Hare Intl to Honolulu flights
O'Hare Intl to San Francisco flights
Minneapolis to Miami flights
O'Hare Intl to New Orleans flights
Minneapolis to Los Angeles flights
O'Hare Intl to George Bush Intcntl flights
O'Hare Intl to San Diego flights
O'Hare Intl to Fort Myers flights
Minneapolis to Dallas/Fort Worth flights
Minneapolis to Fort Lauderdale flights
O'Hare Intl to Santa Ana flights
Minneapolis to Tampa flights
O'Hare Intl to Narita flights
Minneapolis to John F Kennedy Intl flights
O'Hare Intl to Leonardo da Vinci/Fiumicino flights
O'Hare Intl to Suvarnabhumi flights
O'Hare Intl to Baltimore flights
O'Hare Intl to Haneda flights
O'Hare Intl to Dulles Intl flights
O'Hare Intl to West Palm Beach 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 2,629,791 searches. Data last updated noviembre 20, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$157Average$386FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$168Average$420FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$258Average$572FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$274Average$561FlexibilityNo cancel feeOn-time69%
DeltaCheapest$324Average$562FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$325Average$707FlexibilityNo cancel feeOn-time63%
JetBlueCheapest$360Average$591FlexibilityNo cancel feeOn-time62%
Sun Country AirCheapest$398Average$677FlexibilityNo 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.
View all available airlines