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Caribbean Islands

$92+ Cheap flights from Wisconsin to Caribbean Islands

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 11/19. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SJU
oct. 25 — nov. 11
sáb. 10/25
sáb. 11/1
1 adult, Economy
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Cheap flight deals from Wisconsin to Caribbean Islands

Keep the following information in mind while searching for Wisconsin to Caribbean Islands flight deals. Data was last updated septiembre 25, 2025.

Round-trip from

$196
(Cheapflightsfares)

One-way from

$92
(Kiwi.com)

Popular in

June

Cheapest in

September

Average price

$317
From Wisconsin to Caribbean Islands
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One-way flight from Wisconsin to Caribbean Islands
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Highest demand for flights based on searches. 9% potential increase in price ($47 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 September 2025
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Find flight deals from Wisconsin to Caribbean Islands

Cheapest flights from Wisconsin to Caribbean Islands
Explore the most affordable flight options available from Wisconsin to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on septiembre 25, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 9/23. 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.
vie. 10/319:06 pmORD - SJU
Nonstop4h 45mSpirit Airlines
lun. 11/38:43 pmSJU - ORD
Nonstop5h 14mSpirit Airlines
Deal found 9/23$196
This Kiwi.com deal was found by Cheapflights users on 9/23. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 10/179:06 pmORD - SJU
Nonstop4h 45mSpirit Airlines
vie. 10/247:43 pmSJU - ORD
Nonstop5h 14mSpirit Airlines
Deal found 9/23$199
This Kiwi.com deal was found by Cheapflights users on 9/23. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 10/209:06 pmORD - SJU
Nonstop4h 45mMultiple Airlines
dom. 10/269:19 pmSJU - ORD
1 stop10h 51mMultiple Airlines
Deal found 9/23$200
This CheapOair deal was found by Cheapflights users on 9/23. 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.
sáb. 10/253:00 pmORD - SJU
Nonstop4h 40mSpirit Airlines
dom. 11/212:51 pmSJU - ORD
1 stop7h 47mSpirit Airlines
Deal found 9/23$201
This Kiwi.com deal was found by Cheapflights users on 9/23. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 10/209:06 pmORD - SJU
Nonstop4h 45mSpirit Airlines
mar. 10/283:19 pmSJU - ORD
1 stop7h 14mSpirit Airlines
Deal found 9/23$202
This Mytrip deal was found by Cheapflights users on 9/24. 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.
vie. 10/249:06 pmORD - SJU
Nonstop4h 45mSpirit Airlines
vie. 10/315:18 pmSJU - ORD
2 stops27h 32mSpirit Airlines
Deal found 9/24$203
This Cheapflightsfares deal was found by Cheapflights users on 9/23. 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.
sáb. 10/256:58 pmORD - STT
1 stop17h 37mSpirit Airlines
sáb. 11/12:01 pmSTT - ORD
1 stop8h 32mSpirit Airlines
Deal found 9/23$205
This Cheapflightsfares deal was found by Cheapflights users on 9/24. 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.
sáb. 11/12:03 pmORD - SJU
Nonstop4h 39mSpirit Airlines
mié. 11/192:38 pmSJU - ORD
Nonstop5h 22mSpirit Airlines
Deal found 9/24$205
This Kiwi.com deal was found by Cheapflights users on 9/24. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 10/227:43 pmORD - SJU
1 stop14h 13mMultiple Airlines
jue. 10/239:06 pmSJU - ORD
1 stop13h 16mMultiple Airlines
Deal found 9/24$206
This Kiwi.com deal was found by Cheapflights users on 9/24. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 10/209:06 pmORD - SJU
Nonstop4h 45mMultiple Airlines
vie. 10/241:59 amSJU - ORD
1 stop19h 49mMultiple Airlines
Deal found 9/24$207
This Cheapflightsfares deal was found by Cheapflights users on 9/24. 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.
mié. 10/227:43 pmORD - SJU
1 stop14h 13mSpirit Airlines
mié. 10/293:19 pmSJU - ORD
1 stop7h 14mSpirit Airlines
Deal found 9/24$208
This Kiwi.com deal was found by Cheapflights users on 9/23. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 10/156:40 amORD - SJU
1 stop18h 22mMultiple Airlines
sáb. 10/253:19 pmSJU - ORD
1 stop7h 14mMultiple Airlines
Deal found 9/23$209

Cheapflights Fare Finder

 
Customize your flight search to find flights from Wisconsin to Caribbean Islands 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 septiembre 25, 2025.
Use the filters below to find and compare flights from Wisconsin to Caribbean Islands that are best for you.

Fly from

Wisconsin

Fly to

Caribbean Islands

Route

Depart

Return

Price

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

dom. 12/7

11:38 am-11:10 pm

1 stop9h 32m

San Juan Luis Munoz Marin Intl

sáb. 12/13

6:36 pm-11:41 pm

1 stop7h 05m

$235

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

mar. 10/28

6:05 am-2:40 pm

1 stop7h 35m

San Juan Luis Munoz Marin Intl

lun. 11/10

2:05 am-11:29 am

2 stops11h 24m

$235

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

mié. 10/29

5:00 am-2:40 pm

1 stop8h 40m

San Juan Luis Munoz Marin Intl

mié. 11/12

8:30 am-5:17 pm

2 stops10h 47m

$235

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

dom. 12/7

10:25 am-11:10 pm

1 stop10h 45m

San Juan Luis Munoz Marin Intl

vie. 12/12

6:36 pm-11:56 pm

1 stop7h 20m

$235

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

jue. 10/30

1:00 pm-9:22 pm

1 stop7h 22m

San Juan Luis Munoz Marin Intl

lun. 11/3

2:05 am-9:05 am

1 stop9h 00m

$276

MinneapolisSan Juan

MSP - SJU

MSPSJU

Minneapolis St Paul

sáb. 11/8

9:00 am-4:14 pm

Nonstop5h 14m

San Juan Luis Munoz Marin Intl

sáb. 11/15

5:15 pm-9:09 pm

Nonstop5h 54m

$298

MinneapolisSan Juan

MSP - SJU

MSPSJU

Minneapolis St Paul

mar. 10/21

6:55 am-4:25 pm

1 stop8h 30m

San Juan Luis Munoz Marin Intl

sáb. 10/25

3:30 pm-8:04 pm

Nonstop5h 34m

$301

MinneapolisSan Juan

MSP - SJU

MSPSJU

Minneapolis St Paul

sáb. 10/18

8:05 am-2:11 pm

Nonstop5h 06m

San Juan Luis Munoz Marin Intl

sáb. 10/25

2:22 pm-8:30 pm

1 stop7h 08m

$301

MinneapolisSan Juan

MSP - SJU

MSPSJU

Minneapolis St Paul

mar. 10/21

6:00 am-2:44 pm

1 stop7h 44m

San Juan Luis Munoz Marin Intl

vie. 10/24

1:05 am-12:18 pm

2 stops12h 13m

$305

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

lun. 12/8

5:45 am-5:23 pm

1 stop9h 38m

San Juan Luis Munoz Marin Intl

sáb. 12/13

6:36 pm-11:41 pm

1 stop7h 05m

$306

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/25

Showing 1-10 of 60 results
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Best time to book a flight from Wisconsin to Caribbean Islands

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

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

Currently, September is the cheapest month in which you can book a flight from Wisconsin to Caribbean Islands (average of $254). Flying from Wisconsin to Caribbean Islands 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 WI to EPX?

Find hourly flight availability from Wisconsin to Caribbean Islands. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated septiembre 25, 2025.

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

Related info for your journey

Find useful and relevant information for your journey from Wisconsin to Caribbean Islands. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Wisconsin to Caribbean Islands?

    Airlines like Delta, United Airlines, and Sun Country Air fly from Wisconsin to Caribbean Islands in about 5h 14m. The time it takes to get you to your destination can typically vary by up to 4h 18m. The distance from Wisconsin to Caribbean Islands is about 2404 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines to fly from Wisconsin to Caribbean Islands one-way?

    For one-way options, check prices for Frontier. According to our data, you can fly for as low as $99. Users have also found prices from $104 and $109 on Arajet and United Airlines, respectively.

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

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

  • How can I find direct flights from Wisconsin to Caribbean Islands?

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

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

    Yes. Cheapflights offers flight deals from Wisconsin to Caribbean Islands 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 Wisconsin to Caribbean Islands?

    Currently, September is the cheapest month in which you can book a flight from Wisconsin to Caribbean Islands (average of $254). Flying from Wisconsin to Caribbean Islands 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

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Wisconsin to Caribbean Islands

See prices for flight routes from nearby airports that may be better suited for you.
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Top 7 airlines flying from Wisconsin to Caribbean Islands

Discover the top 7 airlines that operate flights from Wisconsin to Caribbean Islands. 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 septiembre 25, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$129Average$230FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$215Average$670FlexibilityNo cancel feeOn-time69%
DeltaCheapest$215Average$669FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$226Average$391FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$274Average$675FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$315Average$754FlexibilityNo cancel feeOn-time63%
Sun Country AirCheapest$540Average$651FlexibilityNo cancel feeOn-time83%

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