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$89+ 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 12/13. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — MKE
Dec 4 — Dec 111
Thu 12/4
Thu 12/11
1 adult, Economy
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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 November 4, 2025.

This Priceline deal was found by Cheapflights users on 11/3. 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.
Mon 12/225:09 pmSJU - MKE
1 stop27h 17mFrontier
Sat 1/107:40 pmMKE - SJU
1 stop29h 10mFrontier
Deal found 11/3$216
This United Airlines deal was found by Cheapflights users on 11/2. 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 12/48:10 amSJU - MKE
1 stop8h 58mUnited Airlines
Wed 12/108:40 amMKE - SJU
2 stops11h 42mUnited Airlines
Deal found 11/2$263
This American Airlines deal was found by Cheapflights users on 11/2. 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 12/48:18 amSJU - MKE
2 stops11h 40mAmerican Airlines
Wed 12/101:08 pmMKE - SJU
2 stops20h 51mAmerican Airlines
Deal found 11/2$295
This Delta deal was found by Cheapflights users on 11/2. 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.
Thu 12/253:44 pmSJU - MKE
1 stop6h 51mDelta
Tue 1/67:02 amMKE - SJU
1 stop7h 50mDelta
Deal found 11/2$300
This Kiwi.com deal was found by Cheapflights users on 11/3. 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 12/226:00 amSJU - MKE
2 stops15h 20mMultiple Airlines
Sat 1/107:40 pmMKE - SJU
1 stop29h 10mMultiple Airlines
Deal found 11/3$325
This Priceline deal was found by Cheapflights users on 11/2. 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.
Mon 12/225:09 pmSJU - MKE
1 stop27h 17mMultiple Airlines
Sun 1/48:15 pmMKE - SJU
1 stop12h 18mMultiple Airlines
Deal found 11/2$345
This Kiwi.com deal was found by Cheapflights users on 11/2. 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.
Wed 12/243:55 amSJU - MKE
1 stop17h 25mMultiple Airlines
Tue 1/68:15 pmMKE - SJU
1 stop28h 35mMultiple Airlines
Deal found 11/2$351
This American Airlines deal was found by Cheapflights users on 11/4. 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.
Tue 11/257:15 amSJU - MKE
1 stop16h 16mAmerican Airlines
Tue 12/23:49 pmMKE - SJU
2 stops16h 20mAmerican Airlines
Deal found 11/4$360
This Delta deal was found by Cheapflights users on 11/3. 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.
Thu 11/133:50 pmSTT - MKE
1 stop10h 05mDelta
Sat 11/155:45 amMKE - STT
1 stop6h 55mDelta
Deal found 11/3$1,395

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 November 4, 2025.

Round-trip from

$216
(Priceline)

One-way from

$89
(CheapOair)

Popular in

July

Cheapest in

February

Average price

$363
From Caribbean to Milwaukee-Mitchell
Search Deals
One-way flight from Caribbean to Milwaukee-Mitchell
Search Deals
Highest demand for flights based on searches. 21% potential increase in price ($106 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
Search Deals

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 November 4, 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

Thu 2/19

11:05 am-6:45 pm

1 stop9h 40m

Milwaukee-Mitchell

Mon 2/23

7:40 pm-9:55 am

1 stop12h 15m

$231

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Thu 1/29

6:27 pm-11:46 pm

1 stop7h 19m

Milwaukee-Mitchell

Mon 2/2

12:17 pm-8:57 pm

1 stop6h 40m

$235

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Thu 12/25

3:44 pm-8:35 pm

1 stop6h 51m

Milwaukee-Mitchell

Tue 1/6

7:02 am-4:52 pm

1 stop7h 50m

$300

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Wed 4/22

3:45 pm-9:12 pm

1 stop6h 27m

Milwaukee-Mitchell

Wed 5/6

11:19 am-4:00 am

1 stop15h 41m

$308

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Wed 12/3

2:05 am-10:44 am

1 stop10h 39m

Milwaukee-Mitchell

Wed 12/10

12:04 pm-9:00 pm

1 stop6h 56m

$359

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Tue 11/25

7:15 am-9:31 pm

1 stop16h 16m

Milwaukee-Mitchell

Tue 12/2

3:49 pm-10:09 am

2 stops16h 20m

$360

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Wed 12/24

11:38 am-7:20 pm

1 stop9h 42m

Milwaukee-Mitchell

Mon 12/29

8:15 pm-10:33 am

1 stop12h 18m

$363

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Wed 1/28

2:05 am-1:53 pm

2 stops13h 48m

Milwaukee-Mitchell

Mon 2/2

10:30 am-10:22 pm

2 stops9h 52m

$364

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Thu 2/19

8:35 am-3:35 pm

1 stop9h 00m

Milwaukee-Mitchell

Mon 2/23

9:44 am-10:22 pm

2 stops10h 38m

$364

Montego BayMilwaukee

MBJ - MKE

MBJMKE

Montego Bay Sangster Intl

Fri 3/6

12:35 pm-11:50 pm

1 stop12h 15m

Milwaukee-Mitchell

Tue 3/10

7:00 am-7:25 pm

1 stop12h 25m

$503

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/2

Showing 1-10 of 49 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, September is the cheapest month in which you can book a flight from Caribbean to Milwaukee (average of $113). Flying from Caribbean to Milwaukee in June is currently the most expensive (average of $184). 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 November 4, 2025.

One of the essential ways to save on airfare from Caribbean to Milwaukee is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the morning could potentially save you up to 21% on airfare.

What is the cheapest day to fly from Caribbean to Milwaukee?

Use this chart to determine the cheapest time to fly round-trip from Caribbean to Milwaukee. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Caribbean to Milwaukee flight should consider departing on Saturday afternoons when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

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 November 4, 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
4,238 reviews

Crew

8.6

Overall

8.0

Boarding

8.1

Comfort

8.0

Food

7.0

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
4,238 reviews
Southwest
8.0
Very good
4,238 reviews

Crew

8.6

Overall

8.0

Boarding

8.1

Comfort

8.0

Food

7.0

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
7.9
Good
8,002 reviews
Southwest
8.0
Very good
4,238 reviews

Crew

8.6

Overall

8.0

Boarding

8.1

Comfort

8.0

Food

7.0

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
8,997 reviews
Southwest
8.0
Very good
4,238 reviews

Crew

8.6

Overall

8.0

Boarding

8.1

Comfort

8.0

Food

7.0

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
11,038 reviews
Southwest
8.0
Very good
4,238 reviews

Crew

8.6

Overall

8.0

Boarding

8.1

Comfort

8.0

Food

7.0

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?

    Frontier, Delta, and American Airlines can get you from Caribbean to Milwaukee in just under 6h 27m. Your travel time can differ by up to 3h 13m. 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 Southwest. Other airlines that offer cheap prices include United Airlines from $118 and Delta 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, Port of Spain Piarco Intl - Milwaukee-Mitchell or Saint Thomas Island Cyril E King - 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, September is the cheapest month in which you can book a flight from Caribbean to Milwaukee (average of $113). Flying from Caribbean to Milwaukee in June is currently the most expensive (average of $184). 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
New Berlin
Oak Creek
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 November 4, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$215Average$399FlexibilityNo cancel feeOn-time69%
DeltaCheapest$215Average$445FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$235Average$437FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$305Average$485FlexibilityNo cancel feeOn-time63%

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