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$113+ 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 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
sáb. 6/21
sáb. 6/28
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 junio 16, 2025.

Round-trip from

$225
(Delta)

One-way from

$113
(Delta)

Popular in

June

Cheapest in

February

Average price

$512
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. 18% potential increase in price ($86 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($12 potential savings vs. average RT price).
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Average for round-trip flights in June 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 junio 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.
jue. 9/412:50 pmSJU - MKE
1 stop11h 46mDelta
jue. 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.
mié. 9/104:42 pmSJU - MKE
2 stops18h 22mAmerican Airlines
mié. 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.
jue. 7/101:37 amSJU - MKE
1 stop8h 13mSpirit Airlines
lun. 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.
jue. 6/1911:25 amSJU - MKE
1 stop11h 35mSouthwest
dom. 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.
mié. 7/231:21 amSJU - MKE
2 stops17h 08mMultiple Airlines
lun. 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.
mar. 9/91:05 amSJU - MKE
2 stops10h 08mUnited Airlines
mié. 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.
vie. 10/105:15 pmSTT - MKE
2 stops20h 27mAmerican Airlines
mar. 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.
sáb. 7/52:09 pmMBJ - MKE
3 stops27h 44mMultiple Airlines
lun. 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.
vie. 10/102:42 pmSTT - MKE
1 stop9h 43mDelta
mar. 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.
jue. 7/1712:30 amPOS - MKE
2 stops17h 20mUnited Airlines
mié. 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.
vie. 7/187:00 amPOS - MKE
2 stops18h 04mAmerican Airlines
mié. 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 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 junio 16, 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

jue. 9/4

12:50 pm-11:36 pm

1 stop11h 46m

Milwaukee-Mitchell

jue. 9/18

12:20 pm-10:08 pm

1 stop8h 48m

$225

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

mié. 9/10

4:42 pm-10:04 am

2 stops18h 22m

Milwaukee-Mitchell

mié. 9/24

3:47 pm-11:11 am

2 stops18h 24m

$230

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

jue. 7/10

1:37 am-8:50 am

1 stop8h 13m

Milwaukee-Mitchell

lun. 7/14

4:37 pm-1:35 am

1 stop7h 58m

$284

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

mié. 7/23

1:21 am-5:29 pm

2 stops17h 08m

Milwaukee-Mitchell

lun. 7/28

9:45 am-11:32 am

1 stop24h 47m

$403

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

mar. 9/9

1:05 am-10:13 am

2 stops10h 08m

Milwaukee-Mitchell

mié. 9/24

10:50 am-11:57 pm

2 stops12h 07m

$405

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

jue. 7/3

11:25 am-10:00 pm

1 stop11h 35m

Milwaukee-Mitchell

sáb. 7/5

8:20 am-4:15 pm

1 stop6h 55m

$470

Saint Thomas IslandMilwaukee

STT - MKE

STTMKE

Saint Thomas Island Cyril E King

vie. 10/10

5:15 pm-12:42 pm

2 stops20h 27m

Milwaukee-Mitchell

mar. 10/14

6:49 pm-12:38 pm

1 stop16h 49m

$509

Montego BayMilwaukee

MBJ - MKE

MBJMKE

Montego Bay Sangster Intl

sáb. 7/5

2:09 pm-5:53 pm

3 stops27h 44m

Milwaukee-Mitchell

lun. 8/25

5:56 pm-11:09 am

3 stops17h 13m

$554

Saint Thomas IslandMilwaukee

STT - MKE

STTMKE

Saint Thomas Island Cyril E King

vie. 10/10

2:42 pm-11:25 pm

1 stop9h 43m

Milwaukee-Mitchell

mar. 10/14

6:00 am-1:32 pm

1 stop6h 32m

$574

Port of SpainMilwaukee

POS - MKE

POSMKE

Port of Spain Piarco Intl

jue. 7/17

12:30 am-4:50 pm

2 stops17h 20m

Milwaukee-Mitchell

mié. 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
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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 junio 16, 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.

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 junio 16, 2025.
Southwest
8.0
Very good
4,278 reviews

Crew

8.6

Comfort

8.0

Overall

8.0

Food

7.1

Boarding

8.2

Entertainment

7.6

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

Comfort

8.0

Overall

8.0

Food

7.1

Boarding

8.2

Entertainment

7.6

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

Comfort

8.0

Overall

8.0

Food

7.1

Boarding

8.2

Entertainment

7.6

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

Comfort

8.0

Overall

8.0

Food

7.1

Boarding

8.2

Entertainment

7.6

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

Comfort

8.0

Overall

8.0

Food

7.1

Boarding

8.2

Entertainment

7.6

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

Comfort

8.0

Overall

8.0

Food

7.1

Boarding

8.2

Entertainment

7.6

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 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.

  • 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 $113 on Delta. Other airlines that offer cheap prices include American Airlines from $121 and Spirit Airlines from $140 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 Culebra - 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 Caribbean?

Book flights to Caribbean 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 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 to Milwaukee

Discover the top 5 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 junio 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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