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$113+ Cheap flights from Caribbean Islands 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 9/4. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — MKE
Jun 21 — Jun 281
Sat 6/21
Sat 6/28
1 adult, Economy
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Cheap flight deals from Caribbean Islands to Milwaukee

Keep the following information in mind while searching for Caribbean Islands to Milwaukee flight deals. Data was last updated June 16, 2025.

Round-trip from

$225
(Delta)

One-way from

$113
(Delta)
From Caribbean Islands to Milwaukee-Mitchell
Search Deals
One-way flight from Caribbean Islands to Milwaukee-Mitchell
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Find flight deals from Caribbean Islands to Milwaukee

Cheapest flights from Caribbean Islands to Milwaukee
Explore the most affordable flight options available from Caribbean Islands to Milwaukee. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 16, 2025.

This Delta deal was found by Cheapflights users on 6/14. 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.
Thu 9/412:50 pmSJU - MKE
1 stop11h 46mDelta
Thu 9/1812:20 pmMKE - SJU
1 stop8h 48mDelta
Deal found 6/14$225
This American Airlines deal was found by Cheapflights users on 6/14. 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.
Wed 9/104:42 pmSJU - MKE
2 stops18h 22mAmerican Airlines
Wed 9/243:47 pmMKE - SJU
2 stops18h 24mAmerican Airlines
Deal found 6/14$230
This eDestinos deal was found by Cheapflights users on 6/14. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/101:37 amSJU - MKE
1 stop8h 13mSpirit Airlines
Mon 7/144:37 pmMKE - SJU
1 stop7h 58mSpirit Airlines
Deal found 6/14$284
This Southwest deal was found by Cheapflights users on 6/14. 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.
Thu 6/1911:25 amSJU - MKE
1 stop11h 35mSouthwest
Sun 6/225:40 amMKE - SJU
1 stop11h 00mSouthwest
Deal found 6/14$379
This SmartFares deal was found by Cheapflights users on 6/16. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/231:21 amSJU - MKE
2 stops17h 08mMultiple Airlines
Mon 7/289:45 amMKE - SJU
1 stop24h 47mMultiple Airlines
Deal found 6/16$403
This United Airlines deal was found by Cheapflights users on 6/14. 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.
Tue 9/91:05 amSJU - MKE
2 stops10h 08mUnited Airlines
Wed 9/2410:50 amMKE - SJU
2 stops12h 07mUnited Airlines
Deal found 6/14$405
This American Airlines deal was found by Cheapflights users on 6/14. 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.
Fri 10/105:15 pmSTT - MKE
2 stops20h 27mAmerican Airlines
Tue 10/146:49 pmMKE - STT
1 stop16h 49mAmerican Airlines
Deal found 6/14$509
This Mytrip deal was found by Cheapflights users on 6/16. 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.
Sat 7/52:09 pmMBJ - MKE
3 stops27h 44mMultiple Airlines
Mon 8/255:56 pmMKE - MBJ
3 stops17h 13mMultiple Airlines
Deal found 6/16$554
This Delta deal was found by Cheapflights users on 6/14. 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.
Fri 10/102:42 pmSTT - MKE
1 stop9h 43mDelta
Tue 10/146:00 amMKE - STT
1 stop6h 32mDelta
Deal found 6/14$574
This United Airlines deal was found by Cheapflights users on 6/14. 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 7/1712:30 amPOS - MKE
2 stops17h 20mUnited Airlines
Wed 7/235:31 pmMKE - POS
2 stops28h 52mUnited Airlines
Deal found 6/14$622
This American Airlines deal was found by Cheapflights users on 6/14. 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.
Fri 7/187:00 amPOS - MKE
2 stops18h 04mAmerican Airlines
Wed 7/236:07 amMKE - POS
2 stops14h 38mAmerican Airlines
Deal found 6/14$785

Cheapflights Fare Finder

Customize your flight search to find flights from Caribbean Islands 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 June 16, 2025.
Use the filters below to find and compare flights from Caribbean Islands to Milwaukee that are best for you.

Fly from

Caribbean Islands

Fly to

Milwaukee

Route

Depart

Return

Price

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Thu 9/4

12:50 pm-11:36 pm

1 stop11h 46m

Milwaukee-Mitchell

Thu 9/18

12:20 pm-10:08 pm

1 stop8h 48m

$225

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Wed 9/10

4:42 pm-10:04 am

2 stops18h 22m

Milwaukee-Mitchell

Wed 9/24

3:47 pm-11:11 am

2 stops18h 24m

$230

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Thu 7/10

1:37 am-8:50 am

1 stop8h 13m

Milwaukee-Mitchell

Mon 7/14

4:37 pm-1:35 am

1 stop7h 58m

$284

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Wed 7/23

1:21 am-5:29 pm

2 stops17h 08m

Milwaukee-Mitchell

Mon 7/28

9:45 am-11:32 am

1 stop24h 47m

$403

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Tue 9/9

1:05 am-10:13 am

2 stops10h 08m

Milwaukee-Mitchell

Wed 9/24

10:50 am-11:57 pm

2 stops12h 07m

$405

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Thu 7/3

11:25 am-10:00 pm

1 stop11h 35m

Milwaukee-Mitchell

Sat 7/5

8:20 am-4:15 pm

1 stop6h 55m

$470

Saint Thomas IslandMilwaukee

STT - MKE

STTMKE

Saint Thomas Island Cyril E King

Fri 10/10

5:15 pm-12:42 pm

2 stops20h 27m

Milwaukee-Mitchell

Tue 10/14

6:49 pm-12:38 pm

1 stop16h 49m

$509

Montego BayMilwaukee

MBJ - MKE

MBJMKE

Montego Bay Sangster Intl

Sat 7/5

2:09 pm-5:53 pm

3 stops27h 44m

Milwaukee-Mitchell

Mon 8/25

5:56 pm-11:09 am

3 stops17h 13m

$554

Saint Thomas IslandMilwaukee

STT - MKE

STTMKE

Saint Thomas Island Cyril E King

Fri 10/10

2:42 pm-11:25 pm

1 stop9h 43m

Milwaukee-Mitchell

Tue 10/14

6:00 am-1:32 pm

1 stop6h 32m

$574

Port of SpainMilwaukee

POS - MKE

POSMKE

Port of Spain Piarco Intl

Thu 7/17

12:30 am-4:50 pm

2 stops17h 20m

Milwaukee-Mitchell

Wed 7/23

5:31 pm-11:23 pm

2 stops28h 52m

$622

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/16

Showing 1-10 of 29 results
1
2
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Best time to book a flight from Caribbean Islands to Milwaukee

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

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

Currently, February is the cheapest month in which you can book a flight from Caribbean Islands to Milwaukee (average of $280). Flying from Caribbean Islands 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 EPX to MKE?

Find hourly flight availability from Caribbean Islands 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 June 16, 2025.

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

Rainfall in Milwaukee by month

Plan your trip to Milwaukee by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Milwaukee ranges from 1.4 - 4.0 inches per month. June is typically the wettest month, when rainfall can reach 4.0 in. January is typically the driest time to visit Milwaukee when rainfall is around 1.4 in.

Temperature in Milwaukee by month

Plan your trip to Milwaukee by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Milwaukee, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 21.2 F).

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 June 16, 2025.
Read through reviews of airlines operating flights from Caribbean Islands to Milwaukee, such as Southwest, Delta and LATAM Airlines. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,278 reviews

Crew

8.6

Entertainment

7.6

Comfort

8.0

Boarding

8.2

Food

7.1

Overall

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Southwest
8.0
Very good
4,278 reviews
Southwest
8.0
Very good
4,278 reviews

Crew

8.6

Entertainment

7.6

Comfort

8.0

Boarding

8.2

Food

7.1

Overall

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Delta
8.0
Very good
7,963 reviews
Southwest
8.0
Very good
4,278 reviews

Crew

8.6

Entertainment

7.6

Comfort

8.0

Boarding

8.2

Food

7.1

Overall

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
LATAM Airlines
7.5
Good
1,785 reviews
Southwest
8.0
Very good
4,278 reviews

Crew

8.6

Entertainment

7.6

Comfort

8.0

Boarding

8.2

Food

7.1

Overall

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
United Airlines
7.4
Good
8,801 reviews
Southwest
8.0
Very good
4,278 reviews

Crew

8.6

Entertainment

7.6

Comfort

8.0

Boarding

8.2

Food

7.1

Overall

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
JetBlue
7.3
Good
2,922 reviews
Southwest
8.0
Very good
4,278 reviews

Crew

8.6

Entertainment

7.6

Comfort

8.0

Boarding

8.2

Food

7.1

Overall

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

Related info for your journey

Find useful and relevant information for your journey from Caribbean Islands 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 Islands?

    If you book a flight to Milwaukee from Caribbean Islands, you will be flying to 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 Caribbean Islands to Milwaukee one-way?

    $113 is the cheapest one-way deal found within the past few days, from Delta. You may also be able to find cheap deals on American Airlines and Spirit Airlines, with prices starting from $121 and $140, respectively.

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

    The most popular route from Caribbean Islands to Milwaukee is San Juan Luis Munoz Marin Intl - Milwaukee-Mitchell. You may also consider Saint Thomas Island Cyril E King - Milwaukee-Mitchell or Culebra - Milwaukee-Mitchell.

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

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

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

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

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

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

    Currently, February is the cheapest month in which you can book a flight from Caribbean Islands to Milwaukee (average of $280). Flying from Caribbean Islands 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 Caribbean Islands?

Book flights to Caribbean Islands if you plan to visit one of these locations
Mequon
Sheboygan
Oak Creek
Wauwatosa

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Caribbean Islands to Milwaukee

See prices for flight routes from nearby airports that may be better suited for you.
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Top 5 airlines flying from Caribbean Islands to Milwaukee

Discover the top 5 airlines that operate flights from Caribbean Islands 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 June 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$182Average$324FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$215Average$419FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$265Average$445FlexibilityNo cancel feeOn-time71%
DeltaCheapest$275Average$436FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$378Average$485FlexibilityNo cancel feeOn-time63%

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