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$104+ 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 3/18. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — MKE
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
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 February 20, 2025.

Round-trip from

$151
(Frontier)

One-way from

$104
(Cheapflightsfares)

Popular in

June

Cheapest in

February

Average price

$303
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. 15% potential increase in price ($73 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 February 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 February 20, 2025.

This Frontier deal was found by Cheapflights users on 2/20. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/102:54 amSJU - MKE
1 stop10h 25mFrontier
Thu 3/271:19 pmMKE - SJU
1 stop11h 30mFrontier
Deal found 2/20$151
This Mytrip deal was found by Cheapflights users on 2/20. 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.
Tue 3/1112:05 pmSJU - MKE
2 stops29h 34mSpirit Airlines
Thu 3/2710:14 amMKE - SJU
1 stop14h 22mSpirit Airlines
Deal found 2/20$193
This Mytrip deal was found by Cheapflights users on 2/20. 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.
Wed 4/23:05 amSJU - MKE
1 stop10h 24mMultiple Airlines
Mon 4/76:32 pmMKE - SJU
1 stop21h 49mMultiple Airlines
Deal found 2/20$194
This American Airlines deal was found by Cheapflights users on 2/20. 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 5/86:20 amSJU - MKE
1 stop11h 20mAmerican Airlines
Sun 5/116:47 amMKE - SJU
1 stop12h 46mAmerican Airlines
Deal found 2/20$315
This Southwest deal was found by Cheapflights users on 2/20. 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 4/35:15 pmSJU - MKE
1 stop7h 05mSouthwest
Mon 4/76:15 pmMKE - SJU
2 stops15h 05mSouthwest
Deal found 2/20$360
This Delta deal was found by Cheapflights users on 2/20. 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 2/207:30 amSJU - MKE
1 stop9h 33mDelta
Tue 2/257:03 amMKE - SJU
1 stop7h 53mDelta
Deal found 2/20$369
This United Airlines deal was found by Cheapflights users on 2/20. 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 4/21:05 amSJU - MKE
1 stop8h 15mUnited Airlines
Mon 4/71:25 pmMKE - SJU
2 stops22h 09mUnited Airlines
Deal found 2/20$414
This Alaska Airlines deal was found by Cheapflights users on 2/20. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/303:07 pmSJU - MKE
2 stops33h 52mAlaska Airlines
Sun 6/16:18 amMKE - SJU
2 stops30h 59mAlaska Airlines
Deal found 2/20$1,887

Find flights from Caribbean to Milwaukee within your budget

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 February 20, 2025.

Fly from

Caribbean

Fly to

Milwaukee

Route

Depart

Return

Price

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Tue 3/11

9:35 pm-12:19 pm

1 stop15h 44m

Milwaukee-Mitchell

Thu 3/27

1:19 pm-9:36 pm

1 stop7h 17m

$153

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Tue 3/11

12:05 pm-4:39 pm

2 stops29h 34m

Milwaukee-Mitchell

Thu 3/27

10:14 am-1:36 am

1 stop14h 22m

$193

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Wed 4/2

3:05 am-12:29 pm

1 stop10h 24m

Milwaukee-Mitchell

Mon 4/7

6:32 pm-5:21 pm

1 stop21h 49m

$194

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Thu 5/8

6:20 am-4:40 pm

1 stop11h 20m

Milwaukee-Mitchell

Sun 5/11

6:47 am-8:33 pm

1 stop12h 46m

$315

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Thu 4/3

5:15 pm-11:20 pm

1 stop7h 05m

Milwaukee-Mitchell

Mon 4/7

6:15 pm-10:20 am

2 stops15h 05m

$360

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Thu 4/17

5:11 pm-11:54 pm

1 stop7h 43m

Milwaukee-Mitchell

Sun 4/20

7:00 am-4:27 pm

1 stop8h 27m

$369

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Wed 4/2

1:05 am-8:20 am

1 stop8h 15m

Milwaukee-Mitchell

Mon 4/7

1:25 pm-12:34 pm

2 stops22h 09m

$414

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Fri 5/30

3:07 pm-11:59 pm

2 stops33h 52m

Milwaukee-Mitchell

Sun 6/1

6:18 am-2:17 pm

2 stops30h 59m

$1,887

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Tue 3/18

3:05 am-9:09 am

1 stop7h 04m

$104

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Fri 4/25

6:15 am-2:47 pm

1 stop9h 32m

$138

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/20

Showing 1-10 of 25 results
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2
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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.

Travel insights for flights from Caribbean to Milwaukee

Get recent, data-driven insights about flights from Caribbean to Milwaukee including ideal travel times, pricing trends, and more.

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 February 20, 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 February 20, 2025.
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Comfort

8.1

Entertainment

7.6

Overall

8.1

Boarding

8.2

Food

7.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Southwest
8.1
Very good
4,411 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Comfort

8.1

Entertainment

7.6

Overall

8.1

Boarding

8.2

Food

7.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Alaska Airlines
8.0
Very good
9,692 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Comfort

8.1

Entertainment

7.6

Overall

8.1

Boarding

8.2

Food

7.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Delta
8.0
Very good
8,220 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Comfort

8.1

Entertainment

7.6

Overall

8.1

Boarding

8.2

Food

7.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

JetBlue
7.4
Good
3,070 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Comfort

8.1

Entertainment

7.6

Overall

8.1

Boarding

8.2

Food

7.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

United Airlines
7.4
Good
8,766 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Comfort

8.1

Entertainment

7.6

Overall

8.1

Boarding

8.2

Food

7.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

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 $104 on Spirit Airlines. Other airlines that offer cheap prices include Delta from $138 and Frontier from $146 one-way.

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

    Most travelers choose San Juan Luis Munoz Marin Intl - Milwaukee-Mitchell, Punta Cana - Milwaukee-Mitchell or Christiansted Henry Rohlsen - 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
Pewaukee
Sheboygan
Oak Creek
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 February 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$265Average$392FlexibilityNo cancel feeOn-time71%
DeltaCheapest$324Average$413FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$370Average$434FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$378Average$478FlexibilityNo cancel feeOn-time63%
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