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Caribbean Islands

$111+ 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
Jun 23 — Jun 301
Mon 6/23
Mon 6/30
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 June 18, 2025.

Round-trip from

$213
(Priceline)

One-way from

$111
(Orbitz)

Popular in

June

Cheapest in

September

Average price

$566
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 ($44 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 June 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 June 18, 2025.

This Priceline deal was found by Cheapflights users on 6/17. 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 6/2411:28 amORD - SJU
1 stop14h 07mFrontier
Mon 6/305:40 amSJU - ORD
1 stop29h 37mFrontier
Deal found 6/17$212
This FlightHub deal was found by Cheapflights users on 6/17. 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.
Tue 7/810:43 amORD - SJU
1 stop12h 22mSpirit Airlines
Tue 7/154:43 pmSJU - ORD
1 stop15h 21mSpirit Airlines
Deal found 6/17$215
This Priceline deal was found by Cheapflights users on 6/15. 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.
Sun 6/2912:03 pmORD - SJU
Nonstop4h 44mMultiple Airlines
Fri 7/410:59 amSJU - ORD
1 stop9h 18mMultiple Airlines
Deal found 6/15$220
This Booking.com deal was found by Cheapflights users on 6/17. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/87:49 pmORD - STT
1 stop15h 41mSpirit Airlines
Tue 7/224:05 pmSTT - ORD
1 stop8h 06mSpirit Airlines
Deal found 6/17$255
This Booking.com deal was found by Cheapflights users on 6/15. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/195:30 amMSP - SJU
1 stop10h 16mSpirit Airlines
Thu 9/251:10 amSJU - MSP
1 stop13h 07mSpirit Airlines
Deal found 6/15$257
This American Airlines deal was found by Cheapflights users on 6/16. 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 8/187:05 pmORD - PUJ
1 stop14h 50mAmerican Airlines
Thu 8/2111:55 amPUJ - ORD
1 stop8h 49mAmerican Airlines
Deal found 6/16$295
This Orbitz deal was found by Cheapflights users on 6/17. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/24:35 amORD - PUJ
Nonstop4h 45mArajet
Sun 12/76:00 pmPUJ - ORD
Nonstop5h 10mArajet
Deal found 6/17$302
This Cheapflightsfares deal was found by Cheapflights users on 6/16. 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.
Tue 7/295:05 amORD - PUJ
1 stop8h 25mSpirit Airlines
Thu 7/313:25 pmPUJ - ORD
1 stop9h 28mSpirit Airlines
Deal found 6/16$306
This Kiwi.com deal was found by Cheapflights users on 6/17. 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.
Tue 7/11:43 pmORD - PUJ
1 stop29h 11mMultiple Airlines
Sat 2/75:47 amPUJ - ORD
Nonstop5h 10mMultiple Airlines
Deal found 6/17$312
This CheapOair deal was found by Cheapflights users on 6/17. 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 11/155:30 amMSP - SJU
1 stop10h 16mMultiple Airlines
Sat 11/225:15 pmSJU - MSP
Nonstop5h 54mMultiple Airlines
Deal found 6/17$320
This Sun Country Air deal was found by Cheapflights users on 6/16. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/159:00 amMSP - SJU
Nonstop5h 14mSun Country Air
Sat 11/225:15 pmSJU - MSP
Nonstop5h 54mSun Country Air
Deal found 6/16$321
This United Airlines deal was found by Cheapflights users on 6/16. 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 9/238:52 amORD - SJU
Nonstop4h 52mUnited Airlines
Sat 9/271:05 amSJU - ORD
1 stop7h 33mUnited Airlines
Deal found 6/16$327

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 June 18, 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

Tue 6/24

11:28 am-2:35 am

1 stop14h 07m

San Juan Luis Munoz Marin Intl

Mon 6/30

5:40 am-10:17 am

1 stop29h 37m

$212

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 7/8

10:43 am-12:05 am

1 stop12h 22m

San Juan Luis Munoz Marin Intl

Tue 7/15

4:43 pm-7:04 am

1 stop15h 21m

$215

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sun 6/29

12:03 pm-5:47 pm

Nonstop4h 44m

San Juan Luis Munoz Marin Intl

Fri 7/4

10:59 am-7:17 pm

1 stop9h 18m

$220

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Tue 7/8

7:49 pm-12:30 pm

1 stop15h 41m

Saint Thomas Island Cyril E King

Tue 7/22

4:05 pm-11:11 pm

1 stop8h 06m

$255

MinneapolisSan Juan

MSP - SJU

MSPSJU

Minneapolis St Paul

Fri 9/19

5:30 am-4:46 pm

1 stop10h 16m

San Juan Luis Munoz Marin Intl

Thu 9/25

1:10 am-1:17 pm

1 stop13h 07m

$257

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Mon 8/18

7:05 pm-10:55 am

1 stop14h 50m

Punta Cana

Thu 8/21

11:55 am-7:44 pm

1 stop8h 49m

$295

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Tue 12/2

4:35 am-11:20 am

Nonstop4h 45m

Punta Cana

Sun 12/7

6:00 pm-9:10 pm

Nonstop5h 10m

$302

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Tue 7/29

5:05 am-2:30 pm

1 stop8h 25m

Punta Cana

Thu 7/31

3:25 pm-11:53 pm

1 stop9h 28m

$306

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Tue 7/1

1:43 pm-7:54 pm

1 stop29h 11m

Punta Cana

Sat 2/7

5:47 am-8:57 am

Nonstop5h 10m

$312

MinneapolisSan Juan

MSP - SJU

MSPSJU

Minneapolis St Paul

Sat 11/15

5:30 am-5:46 pm

1 stop10h 16m

San Juan Luis Munoz Marin Intl

Sat 11/22

5:15 pm-9:09 pm

Nonstop5h 54m

$320

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/17

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 June 18, 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 June 18, 2025.
Peruse reviews from past customers who have flown with Delta, Southwest and Copa Airlines 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
7,965 reviews

Food

7.3

Overall

8.0

Comfort

7.9

Crew

8.5

Boarding

8.2

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,965 reviews
Delta
8.0
Very good
7,965 reviews

Food

7.3

Overall

8.0

Comfort

7.9

Crew

8.5

Boarding

8.2

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Southwest
8.0
Very good
4,280 reviews
Delta
8.0
Very good
7,965 reviews

Food

7.3

Overall

8.0

Comfort

7.9

Crew

8.5

Boarding

8.2

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Copa Airlines
7.5
Good
1,455 reviews
Delta
8.0
Very good
7,965 reviews

Food

7.3

Overall

8.0

Comfort

7.9

Crew

8.5

Boarding

8.2

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
United Airlines
7.4
Good
8,809 reviews
Delta
8.0
Very good
7,965 reviews

Food

7.3

Overall

8.0

Comfort

7.9

Crew

8.5

Boarding

8.2

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
JetBlue
7.3
Good
2,923 reviews
Delta
8.0
Very good
7,965 reviews

Food

7.3

Overall

8.0

Comfort

7.9

Crew

8.5

Boarding

8.2

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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 $111. Users have also found prices from $115 and $123 on Frontier and Spirit 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

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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 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 June 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$129Average$239FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$204Average$475FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$225Average$676FlexibilityNo cancel feeOn-time69%
JetBlueCheapest$248Average$435FlexibilityNo cancel feeOn-time62%
DeltaCheapest$264Average$646FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$269Average$683FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$336Average$749FlexibilityNo cancel feeOn-time63%
Sun Country AirCheapest$498Average$647FlexibilityNo cancel feeOn-time83%

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