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$118+ Cheap flights from Caribbean to Milwaukee (MKE)

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 10/30. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — MKE
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
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Cheap flight deals from Caribbean to Milwaukee

Keep the following information in mind while searching for Caribbean to Milwaukee flight deals. Data was last updated September 15, 2025.

Round-trip from

$235
(American Airlines)

One-way from

$118
(Delta)

Popular in

July

Cheapest in

February

Average price

$328
From Caribbean to Milwaukee-Mitchell
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One-way flight from Caribbean to Milwaukee-Mitchell
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Highest demand for flights based on searches. 21% potential increase in price ($104 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($11 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from Caribbean to Milwaukee

Cheapest flights from Caribbean to Milwaukee
Explore the most affordable flight options available from Caribbean to Milwaukee. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 15, 2025.

This American Airlines deal was found by Cheapflights users on 9/14. 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 10/233:50 pmSJU - MKE
1 stop9h 24mAmerican Airlines
Sun 10/262:05 pmMKE - SJU
1 stop8h 49mAmerican Airlines
Deal found 9/14$235
This American Airlines deal was found by Cheapflights users on 9/15. 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 10/255:25 amSJU - MKE
1 stop16h 26mAmerican Airlines
Wed 10/296:45 amMKE - SJU
2 stops14h 25mAmerican Airlines
Deal found 9/15$241
This United Airlines deal was found by Cheapflights users on 9/13. 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 12/152:05 amSJU - MKE
2 stops11h 24mUnited Airlines
Wed 1/711:30 amMKE - SJU
1 stop7h 30mUnited Airlines
Deal found 9/13$298
This United Airlines deal was found by Cheapflights users on 9/14. 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.
Wed 10/221:05 amSJU - MKE
2 stops10h 06mUnited Airlines
Sun 10/266:05 amMKE - SJU
1 stop7h 35mUnited Airlines
Deal found 9/14$304
This Delta deal was found by Cheapflights users on 9/14. 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 10/187:15 amSJU - MKE
1 stop6h 54mDelta
Sun 10/2610:35 amMKE - SJU
1 stop10h 24mDelta
Deal found 9/14$305
This American Airlines deal was found by Cheapflights users on 9/12. 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 10/165:30 amSJU - MKE
1 stop11h 29mAmerican Airlines
Sun 10/196:00 amMKE - SJU
1 stop16h 59mAmerican Airlines
Deal found 9/12$315
This American Airlines deal was found by Cheapflights users on 9/13. 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 12/42:50 pmSJU - MKE
2 stops10h 40mAmerican Airlines
Wed 12/105:00 amMKE - SJU
2 stops10h 52mAmerican Airlines
Deal found 9/13$317
This United Airlines deal was found by Cheapflights users on 9/14. 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.
Fri 10/171:05 amSJU - MKE
2 stops11h 21mUnited Airlines
Sun 10/2610:53 amMKE - SJU
1 stop8h 07mUnited Airlines
Deal found 9/14$325
This United Airlines deal was found by Cheapflights users on 9/13. 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.
Wed 10/221:05 amSJU - MKE
2 stops10h 06mUnited Airlines
Mon 10/2712:05 pmMKE - SJU
1 stop6h 55mUnited Airlines
Deal found 9/13$336
This Southwest deal was found by Cheapflights users on 9/14. 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 10/35:00 amSJU - MKE
1 stop7h 00mSouthwest
Sun 10/512:40 pmMKE - SJU
1 stop10h 35mSouthwest
Deal found 9/14$337
This United Airlines deal was found by Cheapflights users on 9/14. 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 10/301:55 pmPUJ - MKE
1 stop26h 12mUnited Airlines
Mon 11/35:13 pmMKE - PUJ
1 stop20h 49mUnited Airlines
Deal found 9/14$364
This United Airlines deal was found by Cheapflights users on 9/14. 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.
Wed 10/294:20 pmPUJ - MKE
2 stops18h 58mUnited Airlines
Mon 11/35:13 pmMKE - PUJ
2 stops17h 46mUnited Airlines
Deal found 9/14$385

Cheapflights Fare Finder

 
Customize your flight search to find flights from Caribbean to Milwaukee 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 September 15, 2025.
Use the filters below to find and compare flights from Caribbean to Milwaukee that are best for you.

Fly from

Caribbean

Fly to

Milwaukee

Route

Depart

Return

Price

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Wed 10/22

1:06 pm-8:07 pm

1 stop8h 01m

Milwaukee-Mitchell

Tue 10/28

7:00 am-4:25 pm

1 stop8h 25m

$235

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Sat 10/18

7:15 am-1:09 pm

1 stop6h 54m

Milwaukee-Mitchell

Tue 10/28

7:00 am-4:25 pm

1 stop8h 25m

$235

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Wed 10/22

1:05 am-10:11 am

2 stops10h 06m

Milwaukee-Mitchell

Sun 10/26

6:05 am-2:40 pm

1 stop7h 35m

$304

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Fri 10/24

5:43 pm-11:55 pm

1 stop7h 12m

Milwaukee-Mitchell

Mon 10/27

5:47 am-4:33 pm

1 stop9h 46m

$305

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Sat 10/18

7:15 am-1:09 pm

1 stop6h 54m

Milwaukee-Mitchell

Sun 10/26

10:35 am-9:59 pm

1 stop10h 24m

$305

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Wed 10/22

1:06 pm-8:07 pm

1 stop8h 01m

Milwaukee-Mitchell

Mon 10/27

5:47 am-4:33 pm

1 stop9h 46m

$305

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Thu 12/4

1:57 pm-8:18 pm

1 stop8h 21m

Milwaukee-Mitchell

Wed 12/10

5:45 am-2:14 pm

1 stop6h 29m

$305

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Thu 10/23

1:35 pm-12:14 am

2 stops11h 39m

Milwaukee-Mitchell

Mon 10/27

8:16 pm-2:08 pm

1 stop16h 52m

$317

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Wed 9/24

7:30 am-1:54 pm

1 stop7h 24m

Milwaukee-Mitchell

Tue 10/7

7:00 am-4:25 pm

1 stop8h 25m

$317

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Fri 10/17

1:05 am-10:36 am

1 stop10h 31m

Milwaukee-Mitchell

Sun 10/26

10:53 am-8:00 pm

1 stop8h 07m

$325

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Showing 1-10 of 56 results
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Best time to book a flight from Caribbean to Milwaukee

Have a flexible travel schedule? Discover the best time to fly to Milwaukee from Caribbean 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 Caribbean to Milwaukee

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

Currently, February is the cheapest month in which you can book a flight from Caribbean to Milwaukee (average of $280). Flying from Caribbean to Milwaukee in June is currently the most expensive (average of $376). 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 CB to MKE?

Find hourly flight availability from Caribbean to Milwaukee. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 15, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Caribbean to Milwaukee as you normally would.

Reviews of airlines servicing Milwaukee

Get insights into the airlines that provide service to Milwaukee. 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 Milwaukee. Reviews last updated September 15, 2025.
Read through reviews of airlines operating flights from Caribbean to Milwaukee, such as Southwest, Delta, and United Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,242 reviews

Food

7.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Food

7.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Delta
8.0
Very good
7,954 reviews
Southwest
8.0
Very good
4,242 reviews

Food

7.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
8,929 reviews
Southwest
8.0
Very good
4,242 reviews

Food

7.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,242 reviews

Food

7.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

Related info for your journey

Find useful and relevant information for your journey from Caribbean to Milwaukee. 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 into for flights to Milwaukee from Caribbean?

    For a flight from Caribbean to Milwaukee, you will be flying into Milwaukee-Mitchell. Milwaukee-Mitchell (MKE) is just 6.4 mi from the center of the city.

  • How long is the flight from Caribbean to Milwaukee?

    Delta, United Airlines, and American Airlines can get you from Caribbean to Milwaukee in just under 8h 01m. Your travel time can differ by up to 2h 05m. Airlines will cover a distance of 2120 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines to fly from Caribbean to Milwaukee one-way?

    One-way options have recently been found by users for as low as $118 on Delta. Other airlines that offer cheap prices include American Airlines from $118 and United Airlines from $118 one-way.

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

    Most travelers choose San Juan Luis Munoz Marin Intl - Milwaukee-Mitchell, Saint Thomas Island Cyril E King - Milwaukee-Mitchell or Montego Bay Sangster Intl - Milwaukee-Mitchell when deciding on the best route from Caribbean to Milwaukee.

  • Can I find deals for flights from Caribbean to Milwaukee that include hotel bookings?

    Yes. In addition to deals on Caribbean to Milwaukee flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Caribbean to Milwaukee?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Caribbean to Milwaukee.

  • Can I find deals for business class flights from Caribbean to Milwaukee?

    Yes. Cheapflights offers flight deals from Caribbean to Milwaukee 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 Caribbean to Milwaukee?

    Currently, February is the cheapest month in which you can book a flight from Caribbean to Milwaukee (average of $280). Flying from Caribbean to Milwaukee in June is currently the most expensive (average of $376). 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

Traveling to a place near Milwaukee?

Book flights to Milwaukee if you plan to visit one of these locations
Sheboygan
Oak Creek
New Berlin
Wauwatosa

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Caribbean to Milwaukee

See prices for flight routes from nearby airports that may be better suited for you.
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Top 4 airlines flying from Caribbean to Milwaukee

Discover the top 4 airlines that operate flights from Caribbean to Milwaukee. 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 September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$215Average$404FlexibilityNo cancel feeOn-time69%
DeltaCheapest$215Average$441FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$265Average$449FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$323Average$490FlexibilityNo cancel feeOn-time63%

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