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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 4/29. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SJU
Apr 29 — May 61
Tue 4/29
Tue 5/6
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 April 24, 2025.

Round-trip from

$202
(Cheapflightsfares)

One-way from

$103
(FlightHub)

Popular in

December

Cheapest in

September

Average price

$373
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 ($49 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($17 potential savings vs. average RT price).
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Average for round-trip flights in April 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 April 24, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 4/22. 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 5/107:47 amORD - SJU
1 stop16h 07mSpirit Airlines
Thu 5/151:33 amSJU - ORD
1 stop18h 44mSpirit Airlines
Deal found 4/22$196
This Delta deal was found by Cheapflights users on 4/22. 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 9/167:00 amMKE - SJU
1 stop8h 18mDelta
Tue 9/235:19 pmSJU - MKE
1 stop7h 06mDelta
Deal found 4/22$215
This Booking.com deal was found by Cheapflights users on 4/23. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/104:35 pmORD - SJU
1 stop17h 10mMultiple Airlines
Thu 5/1510:46 amSJU - ORD
1 stop13h 25mMultiple Airlines
Deal found 4/23$238
This eDestinos deal was found by Cheapflights users on 4/23. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/39:00 amMSP - SJU
Nonstop5h 11mSun Country Air
Sat 5/104:15 pmSJU - MSP
Nonstop6h 11mSun Country Air
Deal found 4/23$264
This United Airlines deal was found by Cheapflights users on 4/23. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/73:52 pmMKE - SJU
1 stop7h 02mUnited Airlines
Tue 5/131:05 amSJU - MKE
1 stop8h 12mUnited Airlines
Deal found 4/23$292
This Frontier deal was found by Cheapflights users on 4/23. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/29:00 amORD - SJU
1 stop8h 47mFrontier
Sun 5/410:46 amSJU - ORD
1 stop13h 25mFrontier
Deal found 4/23$298
This CheapOair deal was found by Cheapflights users on 4/23. 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.
Tue 5/206:10 amORD - PUJ
Nonstop4h 41mMultiple Airlines
Sat 5/243:22 pmPUJ - ORD
1 stop9h 43mMultiple Airlines
Deal found 4/23$299
This Delta deal was found by Cheapflights users on 4/23. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/76:55 amMSP - SJU
1 stop8h 49mDelta
Sat 5/104:15 pmSJU - MSP
Nonstop5h 45mDelta
Deal found 4/23$301
This American Airlines deal was found by Cheapflights users on 4/23. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/32:53 pmORD - PUJ
1 stop19h 25mAmerican Airlines
Fri 5/94:53 pmPUJ - ORD
1 stop19h 16mAmerican Airlines
Deal found 4/23$304
This Cheapflightsfares deal was found by Cheapflights users on 4/23. 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.
Fri 7/256:45 amORD - PUJ
Nonstop4h 40mFrontier
Wed 7/305:08 pmPUJ - ORD
Nonstop5h 08mFrontier
Deal found 4/23$307
This Delta deal was found by Cheapflights users on 4/21. 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.
Sun 8/316:00 amORD - SJU
1 stop9h 50mDelta
Fri 9/122:28 pmSJU - ORD
1 stop10h 25mDelta
Deal found 4/21$307
This Mytrip deal was found by Cheapflights users on 4/23. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/247:36 amMSP - SJU
Nonstop5h 11mMultiple Airlines
Sat 5/311:39 pmSJU - MSP
1 stop25h 33mMultiple Airlines
Deal found 4/23$308

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 April 24, 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

Sat 5/10

7:47 am-12:54 am

1 stop16h 07m

San Juan Luis Munoz Marin Intl

Thu 5/15

1:33 am-7:17 pm

1 stop18h 44m

$196

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 5/10

4:35 pm-10:45 am

1 stop17h 10m

San Juan Luis Munoz Marin Intl

Thu 5/15

10:46 am-11:11 pm

1 stop13h 25m

$238

MinneapolisSan Juan

MSP - SJU

MSPSJU

Minneapolis St Paul

Sat 5/3

9:00 am-3:11 pm

Nonstop5h 11m

San Juan Luis Munoz Marin Intl

Sat 5/10

4:15 pm-9:26 pm

Nonstop6h 11m

$264

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Wed 5/7

3:52 pm-11:54 pm

1 stop7h 02m

San Juan Luis Munoz Marin Intl

Tue 5/13

1:05 am-8:17 am

1 stop8h 12m

$292

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Fri 5/2

4:15 pm-12:05 am

1 stop6h 50m

San Juan Luis Munoz Marin Intl

Mon 5/5

6:00 am-6:29 pm

1 stop13h 29m

$298

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Tue 5/20

6:10 am-11:51 am

Nonstop4h 41m

Punta Cana

Sat 5/24

3:22 pm-12:05 am

1 stop9h 43m

$299

MinneapolisSan Juan

MSP - SJU

MSPSJU

Minneapolis St Paul

Wed 5/7

6:55 am-4:44 pm

1 stop8h 49m

San Juan Luis Munoz Marin Intl

Sat 5/10

4:15 pm-9:00 pm

Nonstop5h 45m

$301

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Sat 5/3

2:53 pm-11:18 am

1 stop19h 25m

Punta Cana

Fri 5/9

4:53 pm-11:09 am

1 stop19h 16m

$304

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Sat 5/10

5:05 am-2:17 pm

1 stop8h 12m

Punta Cana

Thu 5/15

12:42 pm-11:29 pm

1 stop11h 47m

$308

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

1:39 pm-2:12 pm

1 stop25h 33m

$308

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/22

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 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 April 24, 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 April 24, 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
7,920 reviews

Food

7.3

Crew

8.5

Comfort

7.9

Boarding

8.2

Entertainment

7.9

Overall

8.0

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
7,920 reviews
Delta
8.0
Very good
7,920 reviews

Food

7.3

Crew

8.5

Comfort

7.9

Boarding

8.2

Entertainment

7.9

Overall

8.0

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
9,918 reviews
Delta
8.0
Very good
7,920 reviews

Food

7.3

Crew

8.5

Comfort

7.9

Boarding

8.2

Entertainment

7.9

Overall

8.0

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
4,287 reviews
Delta
8.0
Very good
7,920 reviews

Food

7.3

Crew

8.5

Comfort

7.9

Boarding

8.2

Entertainment

7.9

Overall

8.0

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
7.6
Good
1,411 reviews
Delta
8.0
Very good
7,920 reviews

Food

7.3

Crew

8.5

Comfort

7.9

Boarding

8.2

Entertainment

7.9

Overall

8.0

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
8,685 reviews
Delta
8.0
Very good
7,920 reviews

Food

7.3

Crew

8.5

Comfort

7.9

Boarding

8.2

Entertainment

7.9

Overall

8.0

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 $105 and $108 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

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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 April 24, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$129Average$245FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$195Average$451FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$248Average$463FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$258Average$675FlexibilityNo cancel feeOn-time69%
DeltaCheapest$264Average$628FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$266Average$657FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$375Average$765FlexibilityNo cancel feeOn-time63%
Sun Country AirCheapest$495Average$646FlexibilityNo cancel feeOn-time83%

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