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$113+ Cheap flights from Milwaukee (MKE) to Caribbean

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 8/30. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SJU
Jun 20 — Jun 271
Fri 6/20
Fri 6/27
1 adult, Economy
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Cheap flight deals from Milwaukee to Caribbean

Keep the following information in mind while searching for Milwaukee to Caribbean flight deals. Data was last updated June 15, 2025.

Round-trip from

$225
(Delta)

One-way from

$113
(American Airlines)

Popular in

June

Cheapest in

September

Average price

$566
From Milwaukee-Mitchell to Caribbean
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One-way flight from Milwaukee-Mitchell to Caribbean
Search Deals
Highest demand for flights based on searches. 9% potential increase in price ($44 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% 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 Milwaukee to Caribbean

Cheapest flights from Milwaukee to Caribbean
Explore the most affordable flight options available from Milwaukee to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 15, 2025.

This Delta deal was found by Cheapflights users on 6/13. 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.
Tue 9/166:00 amMKE - SJU
1 stop9h 08mDelta
Tue 9/237:30 amSJU - MKE
1 stop7h 14mDelta
Deal found 6/13$225
This United Airlines deal was found by Cheapflights users on 6/15. 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 9/2310:50 amMKE - SJU
2 stops12h 07mUnited Airlines
Tue 10/71:05 amSJU - MKE
2 stops10h 06mUnited Airlines
Deal found 6/15$244
This Southwest deal was found by Cheapflights users on 6/15. 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.
Tue 9/236:05 amMKE - SJU
1 stop10h 20mSouthwest
Wed 10/86:10 amSJU - MKE
1 stop11h 05mSouthwest
Deal found 6/15$270
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/57:14 pmMKE - STT
1 stop17h 44mSpirit Airlines
Fri 7/114:05 pmSTT - MKE
1 stop24h 37mSpirit Airlines
Deal found 6/14$273
This American Airlines deal was found by Cheapflights users on 6/13. 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 9/77:04 amMKE - SJU
1 stop6h 55mAmerican Airlines
Sat 9/134:45 pmSJU - MKE
2 stops18h 47mAmerican Airlines
Deal found 6/13$275
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/124:37 pmMKE - SJU
1 stop7h 58mSpirit Airlines
Sun 7/131:37 amSJU - MKE
1 stop8h 13mSpirit Airlines
Deal found 6/14$295
This Booking.com 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/298:51 pmMKE - MBJ
2 stops12h 23mSpirit Airlines
Sat 10/412:11 pmMBJ - MKE
1 stop7h 45mSpirit Airlines
Deal found 6/14$342
This Delta deal was found by Cheapflights users on 6/13. 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.
Tue 7/295:40 amMKE - PUJ
1 stop8h 11mDelta
Thu 8/72:52 pmPUJ - MKE
1 stop10h 07mDelta
Deal found 6/13$351
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.
Tue 7/296:20 amMKE - PUJ
1 stop8h 49mAmerican Airlines
Thu 8/74:15 pmPUJ - MKE
2 stops19h 15mAmerican Airlines
Deal found 6/14$355
This FlightHub deal was found by Cheapflights users on 6/15. 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.
Wed 8/206:00 amMKE - PUJ
1 stop28h 45mSpirit Airlines
Tue 8/2612:40 pmPUJ - MKE
1 stop11h 32mSpirit Airlines
Deal found 6/15$357
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/712:02 pmMKE - SJU
3 stops35h 03mMultiple Airlines
Sun 7/131:37 amSJU - MKE
2 stops17h 10mMultiple Airlines
Deal found 6/14$408
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.
Wed 12/35:00 amMKE - PUJ
2 stops10h 25mUnited Airlines
Fri 12/121:00 pmPUJ - MKE
2 stops11h 28mUnited Airlines
Deal found 6/14$418

Cheapflights Fare Finder

Customize your flight search to find flights from Milwaukee to Caribbean 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 15, 2025.
Use the filters below to find and compare flights from Milwaukee to Caribbean that are best for you.

Fly from

Milwaukee

Fly to

Caribbean

Route

Depart

Return

Price

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Tue 9/16

12:20 pm-10:08 pm

1 stop8h 48m

San Juan Luis Munoz Marin Intl

Tue 9/23

5:19 pm-11:25 pm

1 stop7h 06m

$225

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Sat 11/15

10:53 am-12:36 am

2 stops11h 43m

San Juan Luis Munoz Marin Intl

Tue 11/18

8:10 am-3:07 pm

1 stop8h 57m

$246

MilwaukeeSaint Thomas Island

MKE - STT

MKESTT

Milwaukee-Mitchell

Sat 7/5

7:14 pm-1:58 pm

1 stop17h 44m

Saint Thomas Island Cyril E King

Fri 7/11

4:05 pm-3:42 pm

1 stop24h 37m

$273

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Sun 9/7

7:04 am-2:59 pm

1 stop6h 55m

San Juan Luis Munoz Marin Intl

Sat 9/13

4:45 pm-10:32 am

2 stops18h 47m

$275

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Sat 7/12

4:37 pm-1:35 am

1 stop7h 58m

San Juan Luis Munoz Marin Intl

Sun 7/13

1:37 am-8:50 am

1 stop8h 13m

$295

MilwaukeePunta Cana

MKE - PUJ

MKEPUJ

Milwaukee-Mitchell

Tue 7/29

5:40 am-2:51 pm

1 stop8h 11m

Punta Cana

Thu 8/7

2:52 pm-11:59 pm

1 stop10h 07m

$351

MilwaukeePunta Cana

MKE - PUJ

MKEPUJ

Milwaukee-Mitchell

Tue 7/29

6:20 am-4:09 pm

1 stop8h 49m

Punta Cana

Thu 8/7

4:15 pm-10:30 am

2 stops19h 15m

$355

MilwaukeePunta Cana

MKE - PUJ

MKEPUJ

Milwaukee-Mitchell

Wed 8/20

6:00 am-11:45 am

1 stop28h 45m

Punta Cana

Tue 8/26

12:40 pm-11:12 pm

1 stop11h 32m

$357

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Mon 7/7

12:02 pm-12:05 am

3 stops35h 03m

San Juan Luis Munoz Marin Intl

Sun 7/13

1:37 am-5:47 pm

2 stops17h 10m

$408

MilwaukeePunta Cana

MKE - PUJ

MKEPUJ

Milwaukee-Mitchell

Wed 12/3

5:00 am-5:25 pm

2 stops10h 25m

Punta Cana

Fri 12/12

1:00 pm-10:28 pm

2 stops11h 28m

$418

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/13

Showing 1-10 of 48 results
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Best time to book a flight from Milwaukee to Caribbean

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

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

Currently, September is the cheapest month in which you can book a flight from Milwaukee to Caribbean (average of $254). Flying from Milwaukee to Caribbean in June is currently the most expensive (average of $339). 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 MKE to CB?

Find hourly flight availability from Milwaukee to Caribbean. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated June 15, 2025.

When flying from Milwaukee to Caribbean, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Rainfall in Caribbean by month

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

In terms of precipitation, rainfall in Caribbean ranges from 2.2 - 6.1 inches per month. November is typically the wettest month, when rainfall can reach 6.1 in. February is typically the driest time to visit Caribbean when rainfall is around 2.2 in.

Temperature in Caribbean by month

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

If weather is an important factor for your trip to Caribbean, use this chart to help with planning. For those seeking warmer temperatures, June is the ideal time of year to visit, when temperatures reach an average of 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 77.0 F).

Reviews of airlines servicing Caribbean

Get insights into the airlines that provide service to Caribbean. 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 Caribbean. Reviews last updated June 15, 2025.
Southwest
8.0
Very good
4,285 reviews

Food

7.1

Entertainment

7.6

Crew

8.6

Overall

8.0

Comfort

8.0

Boarding

8.2

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
4,285 reviews
Southwest
8.0
Very good
4,285 reviews

Food

7.1

Entertainment

7.6

Crew

8.6

Overall

8.0

Comfort

8.0

Boarding

8.2

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
7,961 reviews
Southwest
8.0
Very good
4,285 reviews

Food

7.1

Entertainment

7.6

Crew

8.6

Overall

8.0

Comfort

8.0

Boarding

8.2

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
4,285 reviews

Food

7.1

Entertainment

7.6

Crew

8.6

Overall

8.0

Comfort

8.0

Boarding

8.2

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
8,798 reviews
Southwest
8.0
Very good
4,285 reviews

Food

7.1

Entertainment

7.6

Crew

8.6

Overall

8.0

Comfort

8.0

Boarding

8.2

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.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,285 reviews

Food

7.1

Entertainment

7.6

Crew

8.6

Overall

8.0

Comfort

8.0

Boarding

8.2

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 Milwaukee to Caribbean. 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 from for flights from Milwaukee to Caribbean?

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

    One-way options have recently been found by users for as low as $113 on American Airlines. Other airlines that offer cheap prices include Spirit Airlines from $135 and Delta from $153 one-way.

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

    The most popular route from Milwaukee to Caribbean is Milwaukee-Mitchell - San Juan Luis Munoz Marin Intl. You may also consider Milwaukee-Mitchell - Punta Cana or Milwaukee-Mitchell - Oranjestad Reina Beatrix.

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

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

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

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

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

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

    Currently, September is the cheapest month in which you can book a flight from Milwaukee to Caribbean (average of $254). Flying from Milwaukee to Caribbean in June is currently the most expensive (average of $339). 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

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Alternative routes for Milwaukee to Caribbean

See prices for flight routes from nearby airports that may be better suited for you.
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Top 8 airlines flying from Milwaukee to Caribbean

Discover the top 8 airlines that operate flights from Milwaukee to Caribbean. 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 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$129Average$239FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$195Average$474FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$225Average$591FlexibilityNo cancel feeOn-time69%
JetBlueCheapest$248Average$445FlexibilityNo cancel feeOn-time62%
DeltaCheapest$268Average$548FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$269Average$726FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$332Average$750FlexibilityNo cancel feeOn-time63%
Sun Country AirCheapest$495Average$647FlexibilityNo cancel feeOn-time83%

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