HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Caribbean Islands

$103+ 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 6/1. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SJU
May 6 — May 131
Tue 5/6
Tue 5/13
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 May 1, 2025.

Round-trip from

$196
(CheapOair)

One-way from

$103
(FlightHub)

Popular in

December

Cheapest in

September

Average price

$366
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. 3% potential price decrease ($17 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 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 May 1, 2025.

This CheapOair deal was found by Cheapflights users on 4/30. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/258:17 amORD - SJU
1 stop10h 45mSpirit Airlines
Thu 5/298:12 pmSJU - ORD
1 stop13h 38mSpirit Airlines
Deal found 4/30$196
This Delta deal was found by Cheapflights users on 4/30. 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.
Wed 11/127:00 amMKE - SJU
1 stop8h 10mDelta
Wed 11/196:20 pmSJU - MKE
1 stop7h 05mDelta
Deal found 4/30$225
This United Airlines deal was found by Cheapflights users on 4/30. 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.
Wed 9/177:00 amMKE - SJU
1 stop6h 44mUnited Airlines
Sat 9/201:05 amSJU - MKE
2 stops10h 08mUnited Airlines
Deal found 4/30$254
This FlightHub deal was found by Cheapflights users on 4/30. 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.
Sat 5/174:35 pmORD - SJU
1 stop17h 10mMultiple Airlines
Tue 5/203:56 amSJU - ORD
1 stop29h 26mMultiple Airlines
Deal found 4/30$255
This American Airlines deal was found by Cheapflights users on 5/1. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/165:43 pmMKE - SJU
2 stops18h 02mAmerican Airlines
Tue 9/235:25 pmSJU - MKE
2 stops17h 28mAmerican Airlines
Deal found 5/1$275
This FlightHub deal was found by Cheapflights users on 4/30. 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.
Sat 5/109:00 amMSP - SJU
Nonstop5h 11mMultiple Airlines
Sat 5/248:12 pmSJU - MSP
2 stops18h 16mMultiple Airlines
Deal found 4/30$278
This Cheapflightsfares deal was found by Cheapflights users on 5/1. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/2212:22 pmMKE - SJU
1 stop11h 32mSpirit Airlines
Tue 5/271:59 amSJU - MKE
1 stop10h 28mSpirit Airlines
Deal found 5/1$279
This CheapOair deal was found by Cheapflights users on 4/30. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/46:10 amORD - PUJ
Nonstop4h 41mMultiple Airlines
Fri 5/912:42 pmPUJ - ORD
1 stop11h 47mMultiple Airlines
Deal found 4/30$285
This eDestinos deal was found by Cheapflights users on 4/29. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/247:36 amMSP - SJU
Nonstop5h 11mSun Country Air
Sat 5/314:15 pmSJU - MSP
Nonstop6h 11mSun Country Air
Deal found 4/29$286
This eDestinos deal was found by Cheapflights users on 4/30. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/305:10 amORD - SJU
1 stop9h 05mFrontier
Mon 6/23:40 amSJU - ORD
1 stop21h 56mFrontier
Deal found 4/30$288
This Cheapflightsfares deal was found by Cheapflights users on 4/29. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/306:45 amORD - PUJ
Nonstop4h 41mFrontier
Tue 6/35:54 pmPUJ - ORD
Nonstop5h 11mFrontier
Deal found 4/29$289
This American Airlines deal was found by Cheapflights users on 4/30. 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.
Sun 5/115:00 amORD - PUJ
1 stop9h 49mAmerican Airlines
Thu 5/153:16 pmPUJ - ORD
Nonstop5h 20mAmerican Airlines
Deal found 4/30$295

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 May 1, 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

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sun 5/25

8:17 am-8:02 pm

1 stop10h 45m

San Juan Luis Munoz Marin Intl

Thu 5/29

8:12 pm-8:50 am

1 stop13h 38m

$196

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Tue 9/16

7:00 am-4:18 pm

1 stop8h 18m

San Juan Luis Munoz Marin Intl

Tue 9/23

5:19 pm-11:25 pm

1 stop7h 06m

$225

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Wed 9/17

7:00 am-2:44 pm

1 stop6h 44m

San Juan Luis Munoz Marin Intl

Sat 9/20

1:05 am-10:13 am

2 stops10h 08m

$254

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 5/17

4:35 pm-10:45 am

1 stop17h 10m

San Juan Luis Munoz Marin Intl

Tue 5/20

3:56 am-8:22 am

1 stop29h 26m

$255

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Tue 9/16

5:43 pm-12:45 pm

2 stops18h 02m

San Juan Luis Munoz Marin Intl

Tue 9/23

5:25 pm-9:53 am

2 stops17h 28m

$275

MinneapolisSan Juan

MSP - SJU

MSPSJU

Minneapolis St Paul

Sat 5/10

9:00 am-3:11 pm

Nonstop5h 11m

San Juan Luis Munoz Marin Intl

Sat 5/24

8:12 pm-1:28 pm

2 stops18h 16m

$278

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Thu 5/22

12:22 pm-12:54 am

1 stop11h 32m

San Juan Luis Munoz Marin Intl

Tue 5/27

1:59 am-11:27 am

1 stop10h 28m

$279

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Sun 5/4

6:10 am-11:51 am

Nonstop4h 41m

Punta Cana

Fri 5/9

12:42 pm-11:29 pm

1 stop11h 47m

$285

MinneapolisSan Juan

MSP - SJU

MSPSJU

Minneapolis St Paul

Sat 5/24

7:36 am-1:47 pm

Nonstop5h 11m

San Juan Luis Munoz Marin Intl

Sat 5/31

4:15 pm-9:26 pm

Nonstop6h 11m

$286

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Fri 5/30

5:10 am-3:15 pm

1 stop9h 05m

San Juan Luis Munoz Marin Intl

Mon 6/2

3:40 am-12:36 am

1 stop21h 56m

$288

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/30

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 December is currently the most expensive (average of $336). 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 May 1, 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.

Rainfall in Caribbean Islands by month

Plan your trip to Caribbean Islands by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Caribbean Islands ranges from 2.2 - 6.1 inches per month. November is typically the wettest month, when rainfall can reach 6.1 in. February is typically the driest time to visit Caribbean Islands when rainfall is around 2.2 in.

Temperature in Caribbean Islands by month

Plan your trip to Caribbean Islands by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Caribbean Islands, use this chart to help with planning. For those seeking warmer temperatures, June is the ideal time of year to visit, when temperatures reach an average of 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 77.0 F).

Reviews of airlines servicing Caribbean Islands

Get insights into the airlines that provide service to Caribbean Islands. 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 Islands. Reviews last updated May 1, 2025.
Peruse reviews from past customers who have flown with Delta, Alaska Airlines and Southwest from Wisconsin to Caribbean Islands to help guide your decision. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,934 reviews

Entertainment

7.9

Food

7.3

Crew

8.5

Comfort

7.9

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Delta
8.0
Very good
7,934 reviews
Delta
8.0
Very good
7,934 reviews

Entertainment

7.9

Food

7.3

Crew

8.5

Comfort

7.9

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Alaska Airlines
8.0
Very good
9,968 reviews
Delta
8.0
Very good
7,934 reviews

Entertainment

7.9

Food

7.3

Crew

8.5

Comfort

7.9

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Southwest
8.0
Very good
4,294 reviews
Delta
8.0
Very good
7,934 reviews

Entertainment

7.9

Food

7.3

Crew

8.5

Comfort

7.9

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Copa Airlines
7.5
Good
1,415 reviews
Delta
8.0
Very good
7,934 reviews

Entertainment

7.9

Food

7.3

Crew

8.5

Comfort

7.9

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
United Airlines
7.4
Good
8,696 reviews
Delta
8.0
Very good
7,934 reviews

Entertainment

7.9

Food

7.3

Crew

8.5

Comfort

7.9

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

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 Spirit Airlines. According to our data, you can fly for as low as $103. Users have also found prices from $104 and $113 on Frontier 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 December is currently the most expensive (average of $336). 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
LaGuardia to Fort Lauderdale flights
John F Kennedy Intl to Los Angeles flights
Newark to Fort Lauderdale flights
John F Kennedy Intl to Miami flights
Dallas/Fort Worth to LaGuardia flights
LaGuardia to Miami flights
Newark to Miami flights
Newark to Las Vegas flights
Los Angeles to Seattle flights
LaGuardia to Dallas/Fort Worth flights
LaGuardia to O'Hare Intl flights
San Francisco to John F Kennedy Intl flights
Newark to Orlando flights
Dallas/Fort Worth to Seattle flights
Los Angeles to Newark flights
Newark to Cancún flights
Dallas/Fort Worth to Los Angeles flights
Dallas/Fort Worth to O'Hare Intl flights
Dallas/Fort Worth to John F Kennedy Intl flights
O'Hare Intl to Dallas/Fort Worth flights
John F Kennedy Intl to Seattle flights
O'Hare Intl to LaGuardia flights
Seattle to Los Angeles flights
George Bush Intcntl to Cancún flights
Los Angeles to Dallas/Fort Worth flights
John F Kennedy Intl to Las Vegas flights
John F Kennedy Intl to O'Hare Intl flights
Dallas/Fort Worth to Cancún flights
Newark to Dallas/Fort Worth flights
John F Kennedy Intl to Cancún flights
John F Kennedy Intl to Fort Lauderdale flights
Newark to Seattle flights
Dallas/Fort Worth to Newark flights
John F Kennedy Intl to Orlando flights
O'Hare Intl to Cancún flights
Newark to San Francisco flights
LaGuardia to Atlanta flights
Newark to Los Angeles flights
Los Angeles to LaGuardia flights
LaGuardia to Orlando flights
Newark to O'Hare Intl flights
San Francisco to Newark flights
John F Kennedy Intl to Hobby flights
LaGuardia to Los Angeles flights
John F Kennedy Intl to Dallas/Fort Worth flights
Seattle to John F Kennedy Intl flights
John F Kennedy Intl to San Francisco flights
San Jose to Los Angeles flights
John F Kennedy Intl to West Palm Beach flights

Top 8 airlines flying from Wisconsin to Caribbean Islands

Discover the top 8 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 May 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$129Average$244FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$204Average$452FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$233Average$678FlexibilityNo cancel feeOn-time69%
JetBlueCheapest$248Average$463FlexibilityNo cancel feeOn-time62%
DeltaCheapest$264Average$633FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$267Average$671FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$343Average$765FlexibilityNo cancel feeOn-time63%
Sun Country AirCheapest$495Average$646FlexibilityNo 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.