HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Caribbean Islands

$96+ 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 11/15. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SJU
Aug 17 — Aug 241
Sun 8/17
Sun 8/24
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Wisconsin to Caribbean Islands with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 August 12, 2025.

Round-trip from

$215
(Delta)

One-way from

$96
(Cheapflightsfares)

Popular in

June

Cheapest in

September

Average price

$399
From Wisconsin to Caribbean Islands
Search Deals
One-way flight from Wisconsin to Caribbean Islands
Search Deals
Highest demand for flights based on searches. 9% potential increase in price ($47 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($12 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in August 2025
Search Deals

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 August 12, 2025.

This Delta deal was found by Cheapflights users on 8/12. 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 9/167:20 amMKE - SJU
1 stop7h 57mDelta
Tue 9/235:41 pmSJU - MKE
1 stop7h 07mDelta
Deal found 8/12$215
This Cheapflightsfares deal was found by Cheapflights users on 8/11. 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 8/236:56 amORD - SJU
1 stop16h 01mSpirit Airlines
Fri 8/2910:16 pmSJU - ORD
1 stop12h 06mSpirit Airlines
Deal found 8/11$217
This Cheapflightsfares deal was found by Cheapflights users on 8/10. 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.
Mon 8/255:05 amORD - SJU
1 stop15h 43mSpirit Airlines
Wed 8/271:39 pmSJU - ORD
Nonstop5h 11mSpirit Airlines
Deal found 8/10$220
This FlightHub deal was found by Cheapflights users on 8/10. 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.
Sun 8/175:05 amORD - SJU
1 stop15h 43mSpirit Airlines
Fri 8/227:40 pmSJU - ORD
Nonstop5h 03mSpirit Airlines
Deal found 8/10$221
This Cheapflightsfares deal was found by Cheapflights users on 8/9. 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.
Mon 8/186:56 amORD - SJU
1 stop16h 01mSpirit Airlines
Sat 8/237:40 pmSJU - ORD
Nonstop5h 03mSpirit Airlines
Deal found 8/9$227
This Cheapflightsfares deal was found by Cheapflights users on 8/10. 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.
Sun 8/246:56 amORD - SJU
1 stop7h 14mSpirit Airlines
Fri 8/297:40 pmSJU - ORD
Nonstop5h 03mSpirit Airlines
Deal found 8/10$228
This Cheapflightsfares deal was found by Cheapflights users on 8/10. 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.
Wed 9/176:30 amORD - SJU
1 stop13h 26mSpirit Airlines
Fri 9/197:40 pmSJU - ORD
Nonstop5h 16mSpirit Airlines
Deal found 8/10$233
This FlightHub deal was found by Cheapflights users on 8/10. 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 9/176:30 amORD - SJU
1 stop13h 26mSpirit Airlines
Sun 9/217:40 pmSJU - ORD
Nonstop5h 16mSpirit Airlines
Deal found 8/10$234
This Kiwi.com deal was found by Cheapflights users on 8/10. 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.
Sun 8/175:05 amORD - SJU
1 stop15h 43mSpirit Airlines
Wed 8/271:39 pmSJU - ORD
Nonstop5h 11mSpirit Airlines
Deal found 8/10$236
This Priceline deal was found by Cheapflights users on 8/10. 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 8/2210:26 amORD - SJU
1 stop10h 22mMultiple Airlines
Thu 8/287:25 amSJU - ORD
1 stop12h 03mMultiple Airlines
Deal found 8/10$237
This Trip.com deal was found by Cheapflights users on 8/11. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/175:05 amORD - SJU
1 stop15h 43mSpirit Airlines
Thu 8/287:40 pmSJU - ORD
Nonstop5h 03mSpirit Airlines
Deal found 8/11$238
This American Airlines deal was found by Cheapflights users on 8/9. 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 10/111:20 pmMKE - SJU
1 stop8h 45mAmerican Airlines
Thu 10/167:10 amSJU - MKE
1 stop18h 04mAmerican Airlines
Deal found 8/9$240

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 August 12, 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

Tue 10/21

2:04 pm-9:59 pm

1 stop6h 55m

San Juan Luis Munoz Marin Intl

Tue 10/28

1:06 pm-8:07 pm

1 stop8h 01m

$215

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Tue 9/16

2:45 pm-11:11 am

2 stops19h 26m

San Juan Luis Munoz Marin Intl

Tue 9/23

6:10 am-11:43 pm

2 stops18h 33m

$215

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Tue 11/11

7:00 am-5:10 pm

1 stop8h 10m

San Juan Luis Munoz Marin Intl

Thu 11/27

7:30 am-5:28 pm

1 stop11h 58m

$215

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Tue 9/16

7:20 am-4:17 pm

1 stop7h 57m

San Juan Luis Munoz Marin Intl

Tue 9/23

5:41 pm-11:48 pm

1 stop7h 07m

$215

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Wed 11/12

2:45 pm-11:17 pm

1 stop6h 32m

San Juan Luis Munoz Marin Intl

Thu 11/27

7:30 am-5:28 pm

1 stop11h 58m

$215

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Mon 2/2

7:00 am-4:51 pm

1 stop7h 51m

San Juan Luis Munoz Marin Intl

Thu 3/5

6:15 am-11:18 am

1 stop7h 03m

$215

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Wed 12/10

7:00 am-5:10 pm

1 stop8h 10m

San Juan Luis Munoz Marin Intl

Tue 12/16

6:20 pm-11:25 pm

1 stop7h 05m

$215

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Sat 10/18

12:06 pm-9:59 pm

1 stop8h 53m

San Juan Luis Munoz Marin Intl

Thu 10/23

1:06 pm-8:07 pm

1 stop8h 01m

$215

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Wed 10/22

7:00 am-4:25 pm

1 stop8h 25m

San Juan Luis Munoz Marin Intl

Fri 10/24

7:15 am-1:09 pm

1 stop6h 54m

$215

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Tue 10/21

12:06 pm-9:59 pm

1 stop8h 53m

San Juan Luis Munoz Marin Intl

Fri 10/24

5:43 pm-11:55 pm

1 stop7h 12m

$215

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/10

Showing 1-10 of 60 results
1
2
3
...
6

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 August 12, 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.

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

    For one-way options, check prices for Arajet. According to our data, you can fly for as low as $96. Users have also found prices from $98 and $108 on Spirit Airlines and Delta, 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

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Wisconsin to Caribbean Islands

See prices for flight routes from nearby airports that may be better suited for you.
Los Angeles to John F Kennedy Intl flights
John F Kennedy Intl to Los Angeles flights
Dallas/Fort Worth to Seattle flights
John F Kennedy Intl to Cancún flights
Dallas/Fort Worth to O'Hare Intl flights
Dallas/Fort Worth to LaGuardia flights
Dallas/Fort Worth to Las Vegas flights
Dallas/Fort Worth to John F Kennedy Intl flights
John F Kennedy Intl to Miami flights
Newark to Cancún flights
Los Angeles to Honolulu flights
John F Kennedy Intl to Las Vegas flights
LaGuardia to Dallas/Fort Worth flights
San Francisco to John F Kennedy Intl flights
Newark to Miami flights
Newark to Fort Lauderdale flights
Los Angeles to Newark flights
Newark to O'Hare Intl flights
Newark to Los Angeles flights
Los Angeles to Seattle flights
John F Kennedy Intl to O'Hare Intl flights
LaGuardia to Fort Lauderdale flights
O'Hare Intl to Newark flights
LaGuardia to O'Hare Intl flights
O'Hare Intl to LaGuardia flights
O'Hare Intl to Las Vegas flights
O'Hare Intl to Cancún flights
John F Kennedy Intl to Orlando flights
San Francisco to Newark flights
O'Hare Intl to John F Kennedy Intl flights
John F Kennedy Intl to San Francisco flights
John F Kennedy Intl to Dallas/Fort Worth flights
LaGuardia to Miami flights
John F Kennedy Intl to Fort Lauderdale flights
Newark to Las Vegas flights
Dallas/Fort Worth to Newark flights
Newark to Orlando flights
Dallas/Fort Worth to Cancún flights
Los Angeles to Dallas/Fort Worth flights
LaGuardia to Atlanta flights
Los Angeles to LaGuardia flights
Seattle to Las Vegas flights
Seattle to Los Angeles flights
Dallas/Fort Worth to Los Angeles flights
O'Hare Intl to Dallas/Fort Worth flights
Fort Lauderdale to LaGuardia flights
John F Kennedy Intl to Mexico City flights
Dallas/Fort Worth to Denver flights
Atlanta to LaGuardia flights
LaGuardia to Orlando flights

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 August 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$129Average$233FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$208Average$391FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$215Average$676FlexibilityNo cancel feeOn-time69%
DeltaCheapest$225Average$656FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$271Average$679FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$323Average$743FlexibilityNo cancel feeOn-time63%
Sun Country AirCheapest$519Average$648FlexibilityNo cancel feeOn-time83%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.