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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 5/1. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SJU
Apr 8 — Apr 151
Tue 4/8
Tue 4/15
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 3, 2025.

Round-trip from

$174
(Cheapflightsfares)

One-way from

$96
(CheapOair)

Popular in

December

Cheapest in

September

Average price

$380
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. 3% potential price decrease ($16 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 3, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 4/2. 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 4/138:45 amORD - SJU
1 stop14h 01mSpirit Airlines
Fri 4/189:30 pmSJU - ORD
1 stop11h 34mSpirit Airlines
Deal found 4/2$202
This United Airlines deal was found by Cheapflights users on 4/2. 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.
Sat 5/311:25 amMKE - SJU
2 stops11h 32mUnited Airlines
Fri 5/91:05 amSJU - MKE
2 stops11h 52mUnited Airlines
Deal found 4/2$215
This Delta deal was found by Cheapflights users on 4/2. 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.
Sat 5/37:00 amMKE - SJU
1 stop8h 27mDelta
Tue 5/66:35 amSJU - MKE
1 stop9h 37mDelta
Deal found 4/2$225
This CheapOair deal was found by Cheapflights users on 4/2. 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 4/1211:45 amORD - SJU
1 stop11h 01mMultiple Airlines
Thu 4/175:30 amSJU - ORD
1 stop10h 36mMultiple Airlines
Deal found 4/2$241
This American Airlines deal was found by Cheapflights users on 4/2. 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 9/231:55 pmSJU - MKE
2 stops10h 34mAmerican Airlines
Deal found 4/2$258
This American Airlines deal was found by Cheapflights users on 4/2. 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 5/310:42 amMSP - SJU
1 stop17h 18mAmerican Airlines
Fri 5/93:50 pmSJU - MSP
1 stop7h 10mAmerican Airlines
Deal found 4/2$261
This United Airlines deal was found by Cheapflights users on 4/1. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/33:22 pmMSP - SJU
1 stop7h 32mUnited Airlines
Fri 5/91:05 amSJU - MSP
1 stop11h 17mUnited Airlines
Deal found 4/1$271
This Mytrip deal was found by Cheapflights users on 4/2. 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.
Mon 4/283:07 pmMSP - SJU
2 stops16h 19mMultiple Airlines
Sat 5/312:54 amSJU - MSP
2 stops13h 46mMultiple Airlines
Deal found 4/2$276
This Mytrip deal was found by Cheapflights users on 4/2. 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 5/36:00 amMSP - SJU
2 stops26h 32mSpirit Airlines
Sat 5/107:45 pmSJU - MSP
2 stops18h 43mSpirit Airlines
Deal found 4/2$287
This Cheapflightsfares deal was found by Cheapflights users on 4/3. 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 5/39:00 amMSP - SJU
Nonstop5h 11mSun Country Air
Sat 5/104:15 pmSJU - MSP
Nonstop6h 11mSun Country Air
Deal found 4/3$291
This Frontier deal was found by Cheapflights users on 4/2. 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.
Wed 4/92:00 pmORD - SJU
1 stop7h 53mFrontier
Thu 4/105:30 amSJU - ORD
1 stop10h 36mFrontier
Deal found 4/2$291
This Cheapflightsfares deal was found by Cheapflights users on 4/2. 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 4/122:42 pmMSP - SJU
1 stop7h 36mFrontier
Sat 4/195:45 amSJU - MSP
1 stop8h 57mFrontier
Deal found 4/2$292

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 3, 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 4/13

8:45 am-11:46 pm

1 stop14h 01m

San Juan Luis Munoz Marin Intl

Fri 4/18

9:30 pm-8:04 am

1 stop11h 34m

$202

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Sat 5/3

11:25 am-11:57 pm

2 stops11h 32m

San Juan Luis Munoz Marin Intl

Fri 5/9

1:05 am-11:57 am

2 stops11h 52m

$215

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Sat 5/3

7:00 am-4:27 pm

1 stop8h 27m

San Juan Luis Munoz Marin Intl

Tue 5/6

6:35 am-3:12 pm

1 stop9h 37m

$225

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 4/12

11:45 am-11:46 pm

1 stop11h 01m

San Juan Luis Munoz Marin Intl

Tue 4/15

9:28 am-7:04 pm

1 stop10h 36m

$251

MinneapolisSan Juan

MSP - SJU

MSPSJU

Minneapolis St Paul

Sat 5/3

10:42 am-5:00 am

1 stop17h 18m

San Juan Luis Munoz Marin Intl

Fri 5/9

3:50 pm-10:00 pm

1 stop7h 10m

$261

MinneapolisSan Juan

MSP - SJU

MSPSJU

Minneapolis St Paul

Sat 5/3

3:22 pm-11:54 pm

1 stop7h 32m

San Juan Luis Munoz Marin Intl

Fri 5/9

1:05 am-11:22 am

1 stop11h 17m

$271

MinneapolisSan Juan

MSP - SJU

MSPSJU

Minneapolis St Paul

Mon 4/28

3:07 pm-8:26 am

2 stops16h 19m

San Juan Luis Munoz Marin Intl

Sat 5/3

12:54 am-1:40 pm

2 stops13h 46m

$276

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Sat 4/26

6:40 am-8:28 pm

2 stops12h 48m

San Juan Luis Munoz Marin Intl

Sat 5/3

2:35 pm-9:43 pm

1 stop8h 08m

$285

MinneapolisSan Juan

MSP - SJU

MSPSJU

Minneapolis St Paul

Sat 5/3

6:00 am-9:32 am

2 stops26h 32m

San Juan Luis Munoz Marin Intl

Sat 5/10

7:45 pm-1:28 pm

2 stops18h 43m

$287

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

$291

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/1

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 3, 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 3, 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
7,897 reviews

Entertainment

7.9

Crew

8.5

Overall

8.0

Food

7.3

Boarding

8.2

Comfort

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
7,897 reviews
Delta
8.0
Very good
7,897 reviews

Entertainment

7.9

Crew

8.5

Overall

8.0

Food

7.3

Boarding

8.2

Comfort

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
9,827 reviews
Delta
8.0
Very good
7,897 reviews

Entertainment

7.9

Crew

8.5

Overall

8.0

Food

7.3

Boarding

8.2

Comfort

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
4,274 reviews
Delta
8.0
Very good
7,897 reviews

Entertainment

7.9

Crew

8.5

Overall

8.0

Food

7.3

Boarding

8.2

Comfort

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
1,400 reviews
Delta
8.0
Very good
7,897 reviews

Entertainment

7.9

Crew

8.5

Overall

8.0

Food

7.3

Boarding

8.2

Comfort

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
8,619 reviews
Delta
8.0
Very good
7,897 reviews

Entertainment

7.9

Crew

8.5

Overall

8.0

Food

7.3

Boarding

8.2

Comfort

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 $96. Users have also found prices from $102 and $108 on Frontier and American 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 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 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$129Average$245FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$203Average$456FlexibilityNo cancel feeOn-time65%
DeltaCheapest$264Average$629FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$264Average$678FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$265Average$659FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$375Average$765FlexibilityNo cancel feeOn-time63%
JetBlueCheapest$384Average$445FlexibilityNo cancel feeOn-time62%
Sun Country AirCheapest$495Average$646FlexibilityNo cancel feeOn-time83%

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