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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 9/16. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SJU
Jul 6 — Jul 131
Sun 7/6
Sun 7/13
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 July 1, 2025.

Round-trip from

$253
(FlightHub)

One-way from

$113
(Delta)

Popular in

December

Cheapest in

September

Average price

$479

Good round-trip deal

$574 or less
From Milwaukee-Mitchell to Caribbean
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One-way flight from Milwaukee-Mitchell to Caribbean
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Highest demand for flights based on searches. 8% potential increase in price ($38 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 July 2025
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Price to beat on a round-trip flight from Milwaukee-Mitchell to Caribbean.
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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 July 1, 2025.

This FlightHub deal was found by Cheapflights users on 6/30. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/216:00 amMKE - STT
1 stop6h 48mSpirit Airlines
Tue 8/262:43 pmSTT - MKE
1 stop9h 23mSpirit Airlines
Deal found 6/30$253
This FlightHub deal was found by Cheapflights users on 6/29. 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.
Wed 8/206:00 amMKE - PUJ
1 stop28h 45mSpirit Airlines
Tue 8/2612:40 pmPUJ - MKE
1 stop11h 26mSpirit Airlines
Deal found 6/29$343
This FlightHub deal was found by Cheapflights users on 7/1. 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.
Thu 7/174:37 pmMKE - SJU
1 stop7h 58mSpirit Airlines
Thu 7/2411:59 pmSJU - MKE
2 stops9h 51mSpirit Airlines
Deal found 7/1$350
This American Airlines deal was found by Cheapflights users on 6/30. 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.
Wed 9/178:00 amMKE - PUJ
1 stop6h 25mAmerican Airlines
Tue 9/234:25 pmPUJ - MKE
1 stop7h 35mAmerican Airlines
Deal found 6/30$351
This United Airlines deal was found by Cheapflights users on 7/1. 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.
Sat 11/1512:04 pmMKE - SJU
1 stop6h 56mUnited Airlines
Mon 11/172:05 amSJU - MKE
2 stops15h 02mUnited Airlines
Deal found 7/1$360
This American Airlines deal was found by Cheapflights users on 6/30. 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.
Thu 10/26:00 amMKE - SJU
2 stops16h 37mAmerican Airlines
Mon 10/67:10 amSJU - MKE
1 stop18h 01mAmerican Airlines
Deal found 6/30$369
This Delta deal was found by Cheapflights users on 6/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/96:00 amMKE - PUJ
1 stop7h 20mDelta
Fri 11/144:55 pmPUJ - MKE
1 stop8h 30mDelta
Deal found 6/30$375
This Delta deal was found by Cheapflights users on 6/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/247:00 amMKE - SJU
1 stop8h 10mDelta
Thu 12/41:50 pmSJU - MKE
1 stop7h 13mDelta
Deal found 6/30$380
This Priceline deal was found by Cheapflights users on 7/1. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/148:51 pmMKE - MBJ
2 stops14h 50mSpirit Airlines
Sat 10/2512:11 pmMBJ - MKE
1 stop7h 45mSpirit Airlines
Deal found 7/1$392
This Delta deal was found by Cheapflights users on 7/1. 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.
Sun 9/145:40 amMKE - GCM
1 stop5h 56mDelta
Fri 9/1912:52 pmGCM - MKE
1 stop7h 57mDelta
Deal found 7/1$432
This Delta deal was found by Cheapflights users on 6/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/195:27 amMKE - PLS
1 stop6h 08mDelta
Tue 8/262:00 pmPLS - MKE
1 stop10h 36mDelta
Deal found 6/30$436
This Delta deal was found by Cheapflights users on 6/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/267:00 amMKE - MBJ
1 stop8h 33mDelta
Fri 10/314:58 pmMBJ - MKE
1 stop6h 27mDelta
Deal found 6/30$441

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 July 1, 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

MilwaukeeSaint Thomas Island

MKE - STT

MKESTT

Milwaukee-Mitchell

Thu 8/21

6:00 am-1:48 pm

1 stop6h 48m

Saint Thomas Island Cyril E King

Tue 8/26

2:43 pm-11:06 pm

1 stop9h 23m

$253

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-11:06 pm

1 stop11h 26m

$343

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Fri 8/15

6:00 am-3:10 pm

1 stop8h 10m

San Juan Luis Munoz Marin Intl

Fri 8/22

4:05 pm-11:06 pm

1 stop8h 01m

$343

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Sat 8/30

1:50 pm-10:40 pm

1 stop7h 50m

San Juan Luis Munoz Marin Intl

Wed 9/3

11:50 am-9:50 pm

2 stops11h 00m

$345

MilwaukeePunta Cana

MKE - PUJ

MKEPUJ

Milwaukee-Mitchell

Wed 9/17

8:00 am-3:25 pm

1 stop6h 25m

Punta Cana

Tue 9/23

4:25 pm-11:00 pm

1 stop7h 35m

$351

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Sat 8/30

11:24 am-11:59 pm

2 stops11h 35m

San Juan Luis Munoz Marin Intl

Wed 9/3

6:10 am-11:00 pm

2 stops17h 50m

$373

MilwaukeePunta Cana

MKE - PUJ

MKEPUJ

Milwaukee-Mitchell

Sun 11/9

6:00 am-3:20 pm

1 stop7h 20m

Punta Cana

Fri 11/14

4:55 pm-11:25 pm

1 stop8h 30m

$375

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Wed 8/20

4:03 pm-12:49 am

1 stop7h 46m

San Juan Luis Munoz Marin Intl

Thu 8/28

6:00 am-3:08 pm

1 stop10h 08m

$380

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Fri 9/5

7:30 am-4:27 pm

1 stop7h 57m

San Juan Luis Munoz Marin Intl

Tue 9/23

5:41 pm-11:48 pm

1 stop7h 07m

$390

MilwaukeeMontego Bay

MKE - MBJ

MKEMBJ

Milwaukee-Mitchell

Tue 10/14

8:51 pm-11:41 am

2 stops14h 50m

Montego Bay Sangster Intl

Sat 10/25

12:11 pm-7:56 pm

1 stop7h 45m

$392

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/30

Showing 1-10 of 53 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 July 1, 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.

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 July 1, 2025.
Read through reviews of airlines operating flights from Milwaukee to Caribbean, such as Southwest, Delta, and Austrian Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,273 reviews

Boarding

8.2

Food

7.0

Crew

8.6

Entertainment

7.6

Overall

8.0

Comfort

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
4,273 reviews
Southwest
8.0
Very good
4,273 reviews

Boarding

8.2

Food

7.0

Crew

8.6

Entertainment

7.6

Overall

8.0

Comfort

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
7,973 reviews
Southwest
8.0
Very good
4,273 reviews

Boarding

8.2

Food

7.0

Crew

8.6

Entertainment

7.6

Overall

8.0

Comfort

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.
Austrian Airlines
7.6
Good
807 reviews
Southwest
8.0
Very good
4,273 reviews

Boarding

8.2

Food

7.0

Crew

8.6

Entertainment

7.6

Overall

8.0

Comfort

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
8,858 reviews
Southwest
8.0
Very good
4,273 reviews

Boarding

8.2

Food

7.0

Crew

8.6

Entertainment

7.6

Overall

8.0

Comfort

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
2,919 reviews
Southwest
8.0
Very good
4,273 reviews

Boarding

8.2

Food

7.0

Crew

8.6

Entertainment

7.6

Overall

8.0

Comfort

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 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 Delta. Other airlines that offer cheap prices include American Airlines from $115 and Spirit Airlines from $145 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 - Montego Bay Sangster Intl or Milwaukee-Mitchell - Punta Cana.

  • 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 7 airlines flying from Milwaukee to Caribbean

Discover the top 7 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 July 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$129Average$239FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$208Average$470FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$225Average$573FlexibilityNo cancel feeOn-time69%
DeltaCheapest$255Average$551FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$273Average$728FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$325Average$748FlexibilityNo cancel feeOn-time63%
Sun Country AirCheapest$498Average$648FlexibilityNo cancel feeOn-time83%

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