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$108+ 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 10/4. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — MKE
Aug 5 — Aug 121
Tue 8/5
Tue 8/12
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 July 31, 2025.

Round-trip from

$215
(Southwest)

One-way from

$108
(American Airlines)

Popular in

July

Cheapest in

February

Average price

$494
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. 16% potential increase in price ($72 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 July 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 July 31, 2025.

This Southwest deal was found by Cheapflights users on 7/31. 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 9/184:05 pmSJU - MKE
1 stop7h 55mSouthwest
Sun 9/285:45 amMKE - SJU
1 stop6h 30mSouthwest
Deal found 7/31$215
This American Airlines deal was found by Cheapflights users on 7/29. 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 9/104:43 pmSJU - MKE
2 stops18h 21mAmerican Airlines
Sun 9/146:23 pmMKE - SJU
2 stops17h 24mAmerican Airlines
Deal found 7/29$220
This Delta deal was found by Cheapflights users on 7/29. 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 11/66:43 pmSJU - MKE
1 stop7h 12mDelta
Tue 11/117:00 amMKE - SJU
1 stop8h 10mDelta
Deal found 7/29$225
This CheapOair deal was found by Cheapflights users on 7/29. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/134:05 pmSJU - MKE
1 stop8h 01mSpirit Airlines
Sun 8/176:00 amMKE - SJU
1 stop8h 10mSpirit Airlines
Deal found 7/29$273
This United Airlines deal was found by Cheapflights users on 7/29. 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 12/44:52 pmSJU - MKE
1 stop7h 38mUnited Airlines
Wed 12/107:00 amMKE - SJU
2 stops12h 26mUnited Airlines
Deal found 7/29$355
This American Airlines deal was found by Cheapflights users on 7/30. 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.
Sun 9/144:33 pmPUJ - MKE
1 stop8h 36mAmerican Airlines
Sun 9/217:06 amMKE - PUJ
1 stop7h 27mAmerican Airlines
Deal found 7/30$414
This FlightHub deal was found by Cheapflights users on 7/29. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/1712:19 pmMBJ - MKE
2 stops34h 47mSpirit Airlines
Sun 8/246:00 amMKE - MBJ
2 stops29h 14mSpirit Airlines
Deal found 7/29$455
This American Airlines deal was found by Cheapflights users on 7/30. 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 10/105:20 pmSTT - MKE
2 stops21h 28mAmerican Airlines
Tue 10/144:45 pmMKE - STT
2 stops18h 15mAmerican Airlines
Deal found 7/30$509
This American Airlines deal was found by Cheapflights users on 7/29. 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.
Sun 8/2410:25 amMBJ - MKE
1 stop13h 46mAmerican Airlines
Sun 8/315:28 pmMKE - MBJ
2 stops18h 35mAmerican Airlines
Deal found 7/29$540
This Mytrip deal was found by Cheapflights users on 7/30. 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.
Sun 9/143:19 pmPUJ - MKE
3 stops23h 45mSpirit Airlines
Sun 9/2112:53 pmMKE - PUJ
3 stops24h 21mSpirit Airlines
Deal found 7/30$586
This United Airlines deal was found by Cheapflights users on 7/30. 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 10/312:30 amPOS - MKE
1 stop17h 38mUnited Airlines
Sat 10/1810:18 amMKE - POS
1 stop12h 05mUnited Airlines
Deal found 7/30$637
This Mytrip deal was found by Cheapflights users on 7/29. 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.
Sun 8/242:50 pmMBJ - MKE
3 stops25h 49mMultiple Airlines
Sun 8/316:00 amMKE - MBJ
2 stops29h 00mMultiple Airlines
Deal found 7/29$779

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 July 31, 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 9/18

4:05 pm-11:00 pm

1 stop7h 55m

Milwaukee-Mitchell

Sun 9/28

5:45 am-1:15 pm

1 stop6h 30m

$215

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Wed 9/10

4:43 pm-10:04 am

2 stops18h 21m

Milwaukee-Mitchell

Sun 9/14

6:23 pm-12:47 pm

2 stops17h 24m

$220

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Wed 8/13

4:05 pm-11:06 pm

1 stop8h 01m

Milwaukee-Mitchell

Sun 8/17

6:00 am-3:10 pm

1 stop8h 10m

$273

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Tue 10/14

1:05 am-10:45 am

1 stop10h 40m

Milwaukee-Mitchell

Wed 10/22

6:00 am-2:44 pm

1 stop7h 44m

$407

Punta CanaMilwaukee

PUJ - MKE

PUJMKE

Punta Cana

Sun 9/14

4:33 pm-12:09 am

1 stop8h 36m

Milwaukee-Mitchell

Sun 9/21

7:06 am-3:33 pm

1 stop7h 27m

$414

Montego BayMilwaukee

MBJ - MKE

MBJMKE

Montego Bay Sangster Intl

Sun 8/17

12:19 pm-11:06 pm

2 stops34h 47m

Milwaukee-Mitchell

Sun 8/24

6:00 am-11:14 am

2 stops29h 14m

$455

Saint Thomas IslandMilwaukee

STT - MKE

STTMKE

Saint Thomas Island Cyril E King

Fri 10/10

5:20 pm-1:48 pm

2 stops21h 28m

Milwaukee-Mitchell

Tue 10/14

4:45 pm-12:00 pm

2 stops18h 15m

$509

Montego BayMilwaukee

MBJ - MKE

MBJMKE

Montego Bay Sangster Intl

Sun 8/24

10:25 am-12:11 am

1 stop13h 46m

Milwaukee-Mitchell

Sun 8/31

5:28 pm-12:03 pm

2 stops18h 35m

$540

Punta CanaMilwaukee

PUJ - MKE

PUJMKE

Punta Cana

Sun 9/14

3:19 pm-2:04 pm

3 stops23h 45m

Milwaukee-Mitchell

Sun 9/21

12:53 pm-2:14 pm

3 stops24h 21m

$586

Port of SpainMilwaukee

POS - MKE

POSMKE

Port of Spain Piarco Intl

Fri 10/3

12:30 am-8:46 pm

2 stops21h 16m

Milwaukee-Mitchell

Sat 10/18

8:20 am-11:23 pm

2 stops14h 03m

$637

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/30

Showing 1-10 of 27 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 July 31, 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 July 31, 2025.
Read through reviews of airlines operating flights from Caribbean to Milwaukee, such as Southwest, Delta, and LATAM Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,246 reviews

Overall

8.0

Boarding

8.1

Food

7.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Overall

8.0

Boarding

8.1

Food

7.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Delta
8.0
Very good
7,981 reviews
Southwest
8.0
Very good
4,246 reviews

Overall

8.0

Boarding

8.1

Food

7.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
LATAM Airlines
7.5
Good
1,822 reviews
Southwest
8.0
Very good
4,246 reviews

Overall

8.0

Boarding

8.1

Food

7.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
United Airlines
7.4
Good
8,900 reviews
Southwest
8.0
Very good
4,246 reviews

Overall

8.0

Boarding

8.1

Food

7.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,246 reviews

Overall

8.0

Boarding

8.1

Food

7.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

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 $108 on American Airlines. Other airlines that offer cheap prices include Delta from $113 and Spirit Airlines from $125 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 Milwaukee?

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

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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 July 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$215Average$419FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$265Average$447FlexibilityNo cancel feeOn-time71%
DeltaCheapest$265Average$437FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$323Average$485FlexibilityNo cancel feeOn-time63%

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