Caribbean

$101+ 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 3/17. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SJU
Apr 2 — Apr 91
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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 March 3, 2026.

This American Airlines deal was found by Cheapflights users on 2/26. 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 5/26:00 am
MKE
-
SJU
1 stop15h 05m
American Airlines
Tue 5/55:45 am
SJU
-
MKE
2 stops11h 11m
American Airlines
Deal found 2/26$270
This Southwest deal was found by Cheapflights users on 3/1. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/92:15 pm
MKE
-
SJU
1 stop8h 00m
Southwest
Tue 5/125:05 am
SJU
-
MKE
1 stop7h 50m
Southwest
Deal found 3/1$277
This Priceline deal was found by Cheapflights users on 2/27. 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.
Mon 3/238:20 pm
MKE
-
SJU
1 stop12h 37m
Frontier
Thu 3/2612:04 pm
SJU
-
MKE
1 stop9h 02m
Frontier
Deal found 2/27$278
This Priceline deal was found by Cheapflights users on 3/2. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/177:34 pm
MKE
-
SJU
1 stop29h 27m
Frontier
Mon 4/207:15 am
SJU
-
MKE
1 stop7h 37m
Frontier
Deal found 3/2$279
This Frontier deal was found by Cheapflights users on 2/26. 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.
Thu 4/3012:21 pm
MKE
-
SJU
1 stop9h 35m
Frontier
Sat 5/93:08 am
SJU
-
MKE
1 stop9h 00m
Frontier
Deal found 2/26$280
This Priceline deal was found by Cheapflights users on 2/25. 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 3/34:39 pm
MKE
-
SJU
1 stop8h 14m
Frontier
Wed 3/116:30 am
SJU
-
MKE
1 stop12h 20m
Frontier
Deal found 2/25$284
This United Airlines deal was found by Cheapflights users on 2/27. 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 4/2110:45 am
MKE
-
SJU
2 stops9h 39m
United Airlines
Tue 5/51:00 am
SJU
-
MKE
2 stops9h 45m
United Airlines
Deal found 2/27$290
This Expedia deal was found by Cheapflights users on 3/1. 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.
Mon 3/912:36 pm
MKE
-
SJU
1 stop12h 22m
Frontier
Wed 3/116:30 am
SJU
-
MKE
1 stop12h 20m
Frontier
Deal found 3/1$295
This United Airlines deal was found by Cheapflights users on 3/1. 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.
Tue 4/1410:45 am
MKE
-
SJU
2 stops9h 39m
United Airlines
Sat 4/257:40 am
SJU
-
MKE
1 stop7h 07m
United Airlines
Deal found 3/1$299
This United Airlines deal was found by Cheapflights users on 2/26. 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 5/28:33 am
MKE
-
SJU
2 stops14h 17m
United Airlines
Fri 5/81:00 am
SJU
-
MKE
2 stops14h 27m
United Airlines
Deal found 2/26$300
This CheapOair deal was found by Cheapflights users on 3/1. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/114:15 pm
MKE
-
SJU
1 stop7h 36m
Frontier
Wed 4/1510:54 am
SJU
-
MKE
1 stop25h 32m
Frontier
Deal found 3/1$301
This American Airlines deal was found by Cheapflights users on 2/27. 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 4/256:40 pm
MKE
-
MBJ
1 stop17h 33m
American Airlines
Sat 5/22:10 pm
MBJ
-
MKE
1 stop8h 17m
American Airlines
Deal found 2/27$312

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 March 3, 2026.

Round-trip from

$270
(American Airlines)

One-way from

$101
(Orbitz)

Popular in

December

Cheapest in

September

Average price

$464

Good round-trip deal

$488 or less
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 ($87 potential increase over avg. RT price).
Cheapest flight prices on average. 4% potential price decrease ($20 potential savings vs. average RT price).
Average for round-trip flights in March 2026
Price to beat on a round-trip flight from Milwaukee-Mitchell to Caribbean.

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 March 3, 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

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Tue 4/21

10:45 am-9:24 pm

2 stops9h 39m

San Juan Luis Munoz Marin Intl

Tue 5/5

1:00 am-9:45 am

2 stops9h 45m

$290

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Tue 4/28

9:43 am-8:34 pm

1 stop9h 51m

San Juan Luis Munoz Marin Intl

Tue 5/5

1:00 am-10:04 am

1 stop10h 04m

$300

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Sat 5/2

10:20 am-11:50 pm

2 stops12h 30m

San Juan Luis Munoz Marin Intl

Fri 5/8

1:00 am-10:04 am

1 stop10h 04m

$300

MilwaukeeMontego Bay

MKE - MBJ

MKEMBJ

Milwaukee-Mitchell

Wed 5/6

6:42 pm-9:13 am

1 stop14h 31m

Montego Bay Sangster Intl

Mon 5/11

10:17 am-5:51 pm

1 stop7h 34m

$312

MilwaukeeMontego Bay

MKE - MBJ

MKEMBJ

Milwaukee-Mitchell

Sat 4/25

6:32 pm-9:13 am

1 stop14h 41m

Montego Bay Sangster Intl

Sat 5/2

1:15 pm-11:40 pm

1 stop10h 25m

$312

MilwaukeeMontego Bay

MKE - MBJ

MKEMBJ

Milwaukee-Mitchell

Fri 5/1

5:55 am-3:10 pm

2 stops9h 15m

Montego Bay Sangster Intl

Fri 5/8

2:40 pm-7:49 am

2 stops17h 09m

$322

MilwaukeeMontego Bay

MKE - MBJ

MKEMBJ

Milwaukee-Mitchell

Wed 4/29

5:06 am-3:37 pm

2 stops10h 31m

Montego Bay Sangster Intl

Mon 5/4

4:37 pm-10:09 am

2 stops17h 32m

$326

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Tue 5/5

8:33 am-8:38 pm

2 stops11h 05m

San Juan Luis Munoz Marin Intl

Sat 5/9

1:00 am-9:45 am

2 stops9h 45m

$333

MilwaukeeMontego Bay

MKE - MBJ

MKEMBJ

Milwaukee-Mitchell

Tue 3/24

5:45 am-3:28 pm

1 stop9h 43m

Montego Bay Sangster Intl

Thu 3/26

4:49 pm-9:04 am

1 stop16h 15m

$362

MilwaukeeProvidenciales

MKE - PLS

MKEPLS

Milwaukee-Mitchell

Wed 4/8

5:49 pm-12:00 pm

1 stop17h 11m

Providenciales

Thu 4/16

2:05 pm-11:57 pm

1 stop10h 52m

$363

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/26

Showing 1-10 of 60 resultsSorted by cheapest first
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2
3
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6

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, April is the cheapest month in which you can book a flight from Milwaukee to Caribbean (average of $91). Flying from Milwaukee to Caribbean in December is currently the most expensive (average of $195). 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 March 3, 2026.

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 March 3, 2026.
Read through reviews of airlines operating flights from Milwaukee to Caribbean, such as Southwest, Delta, and United Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.

Crew

8.6

Entertainment

7.5

Boarding

8.1

Overall

8.0

Comfort

8.0

Food

7.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Feb 2026

DEN - BDL

Weird they cancelled a direct and rerouted me on a connecting flight to get in 10 hours later. What was the point? Crew and flight were great, but not sure what's going on with Southwest.

Crew

8.6

Entertainment

7.5

Boarding

8.1

Overall

8.0

Comfort

8.0

Food

7.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Feb 2026

DEN - BDL

Weird they cancelled a direct and rerouted me on a connecting flight to get in 10 hours later. What was the point? Crew and flight were great, but not sure what's going on with Southwest.

Crew

8.6

Entertainment

7.5

Boarding

8.1

Overall

8.0

Comfort

8.0

Food

7.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Feb 2026

DEN - BDL

Weird they cancelled a direct and rerouted me on a connecting flight to get in 10 hours later. What was the point? Crew and flight were great, but not sure what's going on with Southwest.

Crew

8.6

Entertainment

7.5

Boarding

8.1

Overall

8.0

Comfort

8.0

Food

7.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Feb 2026

DEN - BDL

Weird they cancelled a direct and rerouted me on a connecting flight to get in 10 hours later. What was the point? Crew and flight were great, but not sure what's going on with Southwest.

Crew

8.6

Entertainment

7.5

Boarding

8.1

Overall

8.0

Comfort

8.0

Food

7.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Feb 2026

DEN - BDL

Weird they cancelled a direct and rerouted me on a connecting flight to get in 10 hours later. What was the point? Crew and flight were great, but not sure what's going on with Southwest.

Crew

8.6

Entertainment

7.5

Boarding

8.1

Overall

8.0

Comfort

8.0

Food

7.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Feb 2026

DEN - BDL

Weird they cancelled a direct and rerouted me on a connecting flight to get in 10 hours later. What was the point? Crew and flight were great, but not sure what's going on with Southwest.

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 9h 39m. United Airlines provides one of the quickest options available for as low as $290. 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 $108 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, April is the cheapest month in which you can book a flight from Milwaukee to Caribbean (average of $91). Flying from Milwaukee to Caribbean in December is currently the most expensive (average of $195). 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.

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 March 3, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$101Average$333FlexibilityNo cancel feeOn-time62%
DeltaCheapest$112Average$589FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$158Average$556FlexibilityNo cancel feeOn-time69%
Spirit AirlinesCheapest$208Average$368FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$256Average$668FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$315Average$723FlexibilityNo cancel feeOn-time63%
Sun Country AirCheapest$497Average$828FlexibilityNo cancel feeOn-time83%

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