Caribbean

$163+ 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 6/28. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SJU
Jul 4 — Jul 111
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Cheap 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 4, 2026.

This American Airlines deal was found by Cheapflights users on 6/3. 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 8/122:49 pm
MKE
-
SJU
1 stop8h 10m
American Airlines
Tue 8/1810:33 am
SJU
-
MKE
2 stops13h 26m
American Airlines
Deal found 6/3$331
This American Airlines deal was found by Cheapflights users on 6/3. 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.
Mon 10/58:16 pm
MKE
-
SJU
1 stop16h 29m
American Airlines
Fri 10/303:50 pm
SJU
-
MKE
1 stop9h 21m
American Airlines
Deal found 6/3$332
This American Airlines deal was found by Cheapflights users on 5/31. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/86:28 am
MKE
-
SJU
2 stops14h 27m
American Airlines
Tue 9/156:27 am
SJU
-
MKE
2 stops16h 21m
American Airlines
Deal found 5/31$351
This United Airlines deal was found by Cheapflights users on 6/1. 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.
Fri 9/45:00 am
MKE
-
SJU
1 stop8h 44m
United Airlines
Sat 9/191:00 am
SJU
-
MKE
2 stops10h 00m
United Airlines
Deal found 6/1$355
This United Airlines deal was found by Cheapflights users on 5/30. 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.
Sat 9/1212:05 pm
MKE
-
SJU
2 stops10h 45m
United Airlines
Fri 9/251:00 am
SJU
-
MKE
2 stops10h 00m
United Airlines
Deal found 5/30$356
This Southwest deal was found by Cheapflights users on 6/3. 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 9/107:00 am
MKE
-
SJU
2 stops8h 55m
Southwest
Mon 9/146:30 am
SJU
-
MKE
1 stop10h 50m
Southwest
Deal found 6/3$365
This American Airlines deal was found by Cheapflights users on 6/3. 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.
Sat 10/3112:37 pm
MKE
-
SJU
1 stop10h 28m
American Airlines
Sat 11/76:44 am
SJU
-
MKE
1 stop16h 47m
American Airlines
Deal found 6/3$366
This American Airlines deal was found by Cheapflights users on 6/3. 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 9/25:00 am
MKE
-
SJU
1 stop17h 15m
American Airlines
Mon 9/77:00 am
SJU
-
MKE
1 stop15h 06m
American Airlines
Deal found 6/3$371
This American Airlines deal was found by Cheapflights users on 6/2. 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 9/36:28 am
MKE
-
SJU
1 stop16h 31m
American Airlines
Mon 9/77:00 am
SJU
-
MKE
1 stop15h 06m
American Airlines
Deal found 6/2$373
This Delta deal was found by Cheapflights users on 5/31. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/175:30 am
MKE
-
SJU
1 stop6h 46m
Delta
Mon 9/282:26 pm
SJU
-
MKE
1 stop7h 26m
Delta
Deal found 5/31$380
This Expedia deal was found by Cheapflights users on 6/1. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/28:53 am
MKE
-
SJU
1 stop13h 36m
Frontier
Wed 7/88:37 pm
SJU
-
MKE
1 stop12h 21m
Frontier
Deal found 6/1$396
This American Airlines deal was found by Cheapflights users on 6/3. 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 12/16:48 pm
MKE
-
STT
2 stops20h 10m
American Airlines
Tue 12/82:49 pm
STT
-
MKE
2 stops10h 41m
American Airlines
Deal found 6/3$420

Find 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 4, 2026.

Round-trip from

$331
(American Airlines)

One-way from

$163
(American Airlines)

Popular in

December

Cheapest in

October

Average price

$475
From Milwaukee-Mitchell to Caribbean
One-way flight from Milwaukee-Mitchell to Caribbean
Highest demand for flights based on searches. 16% potential increase in price ($90 potential increase over avg. RT price).
Cheapest flight prices on average. 4% potential price decrease ($21 potential savings vs. average RT price).
Average for round-trip flights in June 2026

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 4, 2026.
Use the filters below to find and compare flights from Milwaukee to Caribbean that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Thu 8/20

11:00 am-11:05 pm

1 stop11h 05m

San Juan Luis Munoz Marin Intl

Mon 8/24

6:30 am-3:25 pm

2 stops9h 55m

$365

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Thu 10/15

10:20 am-12:35 am

1 stop13h 15m

San Juan Luis Munoz Marin Intl

Mon 10/19

9:45 pm-8:55 am

1 stop12h 10m

$365

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Sun 9/13

5:55 am-1:16 pm

1 stop6h 21m

San Juan Luis Munoz Marin Intl

Sun 9/27

12:58 pm-8:52 pm

1 stop8h 54m

$380

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Tue 9/22

6:00 am-8:38 pm

2 stops13h 38m

San Juan Luis Munoz Marin Intl

Sat 9/26

1:00 am-10:00 am

2 stops10h 00m

$401

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Fri 9/25

12:30 pm-11:05 pm

2 stops9h 35m

San Juan Luis Munoz Marin Intl

Sat 10/3

6:25 am-3:05 pm

2 stops9h 40m

$404

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Mon 10/12

7:45 pm-9:05 am

1 stop12h 20m

San Juan Luis Munoz Marin Intl

Sat 10/17

5:30 am-11:40 am

1 stop7h 10m

$404

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Tue 7/21

6:00 am-10:57 pm

1 stop15h 57m

San Juan Luis Munoz Marin Intl

Wed 7/29

7:00 am-11:44 pm

1 stop17h 44m

$406

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Wed 9/16

6:00 am-8:38 pm

2 stops13h 38m

San Juan Luis Munoz Marin Intl

Sat 9/19

1:00 am-10:00 am

2 stops10h 00m

$416

MilwaukeeSaint Thomas Island

MKE - STT

MKESTT

Milwaukee-Mitchell

Tue 12/1

6:48 pm-4:58 pm

2 stops20h 10m

Saint Thomas Island Cyril E King

Tue 12/8

2:49 pm-11:30 pm

2 stops10h 41m

$420

MilwaukeeSaint Thomas Island

MKE - STT

MKESTT

Milwaukee-Mitchell

Fri 8/14

5:34 am-1:34 pm

1 stop7h 00m

Saint Thomas Island Cyril E King

Thu 8/20

2:49 pm-11:53 pm

1 stop10h 04m

$420

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/2

Showing 1-10 of 60 resultsSorted by cheapest first
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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, October is the cheapest month in which you can book a flight from Milwaukee to Caribbean (average of $108). Flying from Milwaukee to Caribbean in March is currently the most expensive (average of $1,003). 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.

How far ahead should I book a flight from Milwaukee to Caribbean?

The best time to book flights from Milwaukee to Caribbean is 42 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

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 4, 2026.
Read through reviews of airlines operating flights from Milwaukee to Caribbean, such as Southwest,Delta, andUnited Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.

Food

7.0

Crew

8.6

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Walter,May 2026

LAS - BUR

Short but excellent flight. Everyone was friendly and professional it was a great flight!

Food

7.0

Crew

8.6

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Walter,May 2026

LAS - BUR

Short but excellent flight. Everyone was friendly and professional it was a great flight!

Food

7.0

Crew

8.6

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Walter,May 2026

LAS - BUR

Short but excellent flight. Everyone was friendly and professional it was a great flight!

Food

7.0

Crew

8.6

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Walter,May 2026

LAS - BUR

Short but excellent flight. Everyone was friendly and professional it was a great flight!

Food

7.0

Crew

8.6

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Walter,May 2026

LAS - BUR

Short but excellent flight. Everyone was friendly and professional it was a great flight!

Food

7.0

Crew

8.6

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Walter,May 2026

LAS - BUR

Short but excellent flight. Everyone was friendly and professional it was a great flight!

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.

  • How long is the flight from Milwaukee to Caribbean?

    A quick flight from Milwaukee to Caribbean can take about 6h 21m. Southwest provides one of the quickest options available for as low as $380. Airlines will cover a distance of 2120 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • 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 $90 on Frontier. Other airlines that offer cheap prices include Southwest from $108 and Delta from $112 one-way.

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

  • 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, October is the cheapest month in which you can book a flight from Milwaukee to Caribbean (average of $108). Flying from Milwaukee to Caribbean in March is currently the most expensive (average of $1,003). 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

Browse thousands of different options on Cheapflights for your next trip

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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.

Top 6 airlines flying from Milwaukee to Caribbean

Discover the top 6 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 4, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$112Average$573FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$156Average$360FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$225Average$554FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$256Average$667FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$315Average$734FlexibilityNo cancel feeOn-time63%
Sun Country AirCheapest$547Average$841FlexibilityNo cancel feeOn-time83%

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