Caribbean

$138+ 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 7/21. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SJU
Jun 10 — Jun 171
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Cheap 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 May 11, 2026.

This American Airlines deal was found by Cheapflights users on 5/11. 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 9/55:00 am
MKE
-
SJU
1 stop16h 52m
American Airlines
Wed 9/96:30 am
SJU
-
MKE
2 stops16h 24m
American Airlines
Deal found 5/11$351
This United Airlines deal was found by Cheapflights users on 5/6. 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.
Thu 11/128:45 pm
MKE
-
MBJ
1 stop16h 01m
United Airlines
Tue 11/172:48 pm
MBJ
-
MKE
1 stop10h 21m
United Airlines
Deal found 5/6$352
This American Airlines deal was found by Cheapflights users on 5/11. 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 6/15:53 pm
MKE
-
MBJ
2 stops17h 26m
American Airlines
Fri 6/55:17 pm
MBJ
-
MKE
2 stops18h 47m
American Airlines
Deal found 5/11$357
This American Airlines deal was found by Cheapflights users on 5/9. 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 11/96:48 pm
MKE
-
MBJ
1 stop14h 20m
American Airlines
Mon 11/162:19 pm
MBJ
-
MKE
1 stop18h 41m
American Airlines
Deal found 5/9$358
This Priceline deal was found by Cheapflights users on 5/10. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/168:43 am
MKE
-
SJU
1 stop16h 28m
Frontier
Mon 7/204:05 pm
SJU
-
MKE
1 stop16h 53m
Frontier
Deal found 5/10$361
This Delta deal was found by Cheapflights users on 5/7. 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.
Wed 7/296:50 am
MKE
-
MBJ
1 stop8h 44m
Delta
Wed 8/51:09 pm
MBJ
-
MKE
1 stop10h 44m
Delta
Deal found 5/7$362
This American Airlines deal was found by Cheapflights users on 5/7. 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 6/296:50 pm
MKE
-
MBJ
2 stops18h 18m
American Airlines
Sat 7/43:02 pm
MBJ
-
MKE
1 stop26h 15m
American Airlines
Deal found 5/7$364
This Southwest deal was found by Cheapflights users on 5/6. 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 7/299:25 am
MKE
-
SJU
1 stop13h 20m
Southwest
Wed 8/55:15 am
SJU
-
MKE
1 stop6h 40m
Southwest
Deal found 5/6$365
This American Airlines deal was found by Cheapflights users on 5/10. 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 8/178:20 am
MKE
-
SJU
1 stop13h 47m
American Airlines
Fri 8/211:38 pm
SJU
-
MKE
2 stops10h 21m
American Airlines
Deal found 5/10$366
This American Airlines deal was found by Cheapflights users on 5/11. 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 8/126:33 am
MKE
-
SJU
2 stops13h 41m
American Airlines
Tue 8/186:51 am
SJU
-
MKE
1 stop17h 32m
American Airlines
Deal found 5/11$371
This American Airlines deal was found by Cheapflights users on 5/11. 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.
Thu 9/36:16 am
MKE
-
SJU
2 stops11h 08m
American Airlines
Tue 9/82:33 pm
SJU
-
MKE
1 stop7h 35m
American Airlines
Deal found 5/11$376
This Southwest deal was found by Cheapflights users on 5/7. 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 9/210:00 am
MKE
-
SJU
2 stops11h 00m
Southwest
Sun 9/66:00 am
SJU
-
MKE
1 stop7h 40m
Southwest
Deal found 5/7$387

Find flight deals from Milwaukee to Caribbean

Keep the following information in mind while searching for Milwaukee to Caribbean flight deals. Data was last updated May 11, 2026.

Round-trip from

$326
(Delta)

One-way from

$138
(Priceline)

Popular in

December

Cheapest in

September

Average price

$415
From Milwaukee-Mitchell to Caribbean
One-way flight from Milwaukee-Mitchell to Caribbean
Highest demand for flights based on searches. 17% potential increase in price ($92 potential increase over avg. RT price).
Cheapest flight prices on average. 4% potential price decrease ($21 potential savings vs. average RT price).
Average for round-trip flights in May 2026

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 May 11, 2026.
Use the filters below to find and compare flights from Milwaukee to Caribbean that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

MilwaukeeMontego Bay

MKE - MBJ

MKEMBJ

Milwaukee-Mitchell

Thu 8/27

4:25 pm-11:42 am

2 stops19h 17m

Montego Bay Sangster Intl

Mon 8/31

5:13 pm-11:37 am

2 stops18h 24m

$357

MilwaukeeMontego Bay

MKE - MBJ

MKEMBJ

Milwaukee-Mitchell

Wed 7/29

6:50 am-3:34 pm

1 stop8h 44m

Montego Bay Sangster Intl

Wed 8/5

1:09 pm-11:53 pm

1 stop10h 44m

$362

MilwaukeeMontego Bay

MKE - MBJ

MKEMBJ

Milwaukee-Mitchell

Mon 6/29

6:20 am-3:10 pm

2 stops8h 50m

Montego Bay Sangster Intl

Sat 7/4

2:40 pm-7:00 am

2 stops16h 20m

$391
Quickest round-trip

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Fri 7/31

3:15 pm-11:35 pm

1 stop7h 20m

San Juan Luis Munoz Marin Intl

Tue 8/4

10:30 am-4:20 pm

1 stop6h 50m

$404

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Mon 6/15

1:30 pm-10:45 pm

1 stop8h 15m

San Juan Luis Munoz Marin Intl

Mon 6/22

7:00 am-11:59 pm

1 stop17h 59m

$406

MilwaukeeMontego Bay

MKE - MBJ

MKEMBJ

Milwaukee-Mitchell

Mon 6/1

6:17 pm-11:19 am

1 stop17h 02m

Montego Bay Sangster Intl

Fri 6/5

3:00 pm-11:47 pm

1 stop8h 47m

$434

MilwaukeeMontego Bay

MKE - MBJ

MKEMBJ

Milwaukee-Mitchell

Mon 6/1

6:17 pm-1:08 pm

2 stops18h 51m

Montego Bay Sangster Intl

Sat 6/6

3:00 pm-11:47 pm

1 stop8h 47m

$439

MilwaukeeMontego Bay

MKE - MBJ

MKEMBJ

Milwaukee-Mitchell

Wed 7/29

6:17 pm-1:09 pm

2 stops18h 52m

Montego Bay Sangster Intl

Wed 8/5

12:38 pm-11:50 pm

2 stops11h 12m

$444

MilwaukeeMontego Bay

MKE - MBJ

MKEMBJ

Milwaukee-Mitchell

Sat 6/27

7:49 pm-1:31 pm

1 stop17h 42m

Montego Bay Sangster Intl

Sat 7/4

3:02 pm-5:17 pm

1 stop26h 15m

$447

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Sun 8/2

6:15 am-11:55 pm

2 stops16h 40m

San Juan Luis Munoz Marin Intl

Sun 8/16

9:25 pm-8:55 am

1 stop12h 30m

$448

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/6

Showing 1-10 of 60 resultsSorted by cheapest first
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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

How far ahead should I book a flight from Milwaukee to Caribbean?

The best time to book flights from Milwaukee to Caribbean is 42 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

What is the cheapest month to book a flight from Milwaukee to Caribbean?

Currently, April is the cheapest month in which you can book a flight from Milwaukee to Caribbean (average of $101). Flying from Milwaukee to Caribbean in March is currently the most expensive (average of $968). 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.

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 May 11, 2026.
Read through reviews of airlines operating flights from Milwaukee to Caribbean, such as Southwest,Delta, andUnited Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.

Entertainment

7.5

Crew

8.6

Comfort

8.0

Boarding

8.1

Overall

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

Entertainment

7.5

Crew

8.6

Comfort

8.0

Boarding

8.1

Overall

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

Entertainment

7.5

Crew

8.6

Comfort

8.0

Boarding

8.1

Overall

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

Entertainment

7.5

Crew

8.6

Comfort

8.0

Boarding

8.1

Overall

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

Entertainment

7.5

Crew

8.6

Comfort

8.0

Boarding

8.1

Overall

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

Entertainment

7.5

Crew

8.6

Comfort

8.0

Boarding

8.1

Overall

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

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.

  • How long is the flight from Milwaukee to Caribbean?

    A quick flight from Milwaukee to Caribbean can take about 8h 44m. American Airlines provides one of the quickest options available for as low as $362. Airlines will cover a distance of 1786 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • 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 $90 on Frontier. Other airlines that offer cheap prices include Southwest from $108 and Delta from $112 one-way.

  • What are the most popular routes from Milwaukee to Caribbean?

  • 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, April is the cheapest month in which you can book a flight from Milwaukee to Caribbean (average of $101). Flying from Milwaukee to Caribbean in March is currently the most expensive (average of $968). 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.

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 May 11, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$112Average$562FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$156Average$360FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$202Average$560FlexibilityNo cancel feeOn-time69%
Spirit AirlinesCheapest$219Average$367FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$256Average$664FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$315Average$714FlexibilityNo cancel feeOn-time63%
Sun Country AirCheapest$547Average$841FlexibilityNo cancel feeOn-time83%

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