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$90+ Cheap flights from Wisconsin to Caribbean

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 4/27. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SJU
Apr 6 — Apr 131
Sun 4/6
Sun 4/13
1 adult, Economy
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Cheap flight deals from Wisconsin to Caribbean

Keep the following information in mind while searching for Wisconsin to Caribbean flight deals. Data was last updated April 1, 2025.

Round-trip from

$182
(Cheapflightsfares)

One-way from

$90
(eDestinos)

Popular in

December

Cheapest in

September

Average price

$380

Good round-trip deal

$574 or less
From Wisconsin to Caribbean
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One-way flight from Wisconsin to Caribbean
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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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Price to beat on a round-trip flight from Wisconsin to Caribbean.
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Find flight deals from Wisconsin to Caribbean

Cheapest flights from Wisconsin to Caribbean
Explore the most affordable flight options available from Wisconsin to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 1, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 3/30. 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 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
Wed 4/306:35 amSJU - ORD
Nonstop5h 23mSpirit Airlines
Deal found 3/30$182
This United Airlines deal was found by Cheapflights users on 3/31. 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 5/31:10 pmMKE - SJU
2 stops9h 47mUnited Airlines
Fri 5/91:05 amSJU - MKE
2 stops13h 42mUnited Airlines
Deal found 3/31$215
This Mytrip deal was found by Cheapflights users on 3/30. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/52:45 pmMSP - SJU
1 stop18h 47mMultiple Airlines
Thu 5/812:36 pmSJU - MSP
2 stops25h 10mMultiple Airlines
Deal found 3/30$255
This United Airlines deal was found by Cheapflights users on 3/31. 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 5/310:00 amMSP - SJU
2 stops12h 57mUnited Airlines
Sat 5/103:56 pmSJU - MSP
1 stop8h 19mUnited Airlines
Deal found 3/31$261
This FlightHub deal was found by Cheapflights users on 3/31. 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 4/157:00 pmORD - SJU
1 stop12h 26mMultiple Airlines
Sun 4/205:55 amSJU - ORD
1 stop10h 11mMultiple Airlines
Deal found 3/31$264
This CheapOair deal was found by Cheapflights users on 3/30. 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.
Sat 4/2611:45 amORD - STT
2 stops21h 15mSpirit Airlines
Sat 5/311:05 amSTT - ORD
1 stop14h 53mSpirit Airlines
Deal found 3/30$265
This Delta deal was found by Cheapflights users on 3/31. 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
Sat 5/106:15 amSJU - MKE
1 stop8h 39mDelta
Deal found 3/31$265
This Mytrip deal was found by Cheapflights users on 3/31. 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 4/146:00 amMSP - SJU
2 stops25h 26mSpirit Airlines
Thu 4/175:10 pmSJU - MSP
2 stops21h 30mSpirit Airlines
Deal found 3/31$271
This American Airlines deal was found by Cheapflights users on 3/31. 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 9/2311:55 amSJU - MKE
2 stops12h 34mAmerican Airlines
Deal found 3/31$285
This Booking.com deal was found by Cheapflights users on 3/31. 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.
Thu 4/31:24 pmMKE - SJU
1 stop12h 16mMultiple Airlines
Mon 4/73:00 amSJU - MKE
1 stop15h 37mMultiple Airlines
Deal found 3/31$287
This Cheapflightsfares deal was found by Cheapflights users on 3/31. 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 4/58:54 amMSP - SJU
Nonstop5h 11mSun Country Air
Wed 4/91:45 pmSJU - MSP
Nonstop6h 11mSun Country Air
Deal found 3/31$291
This Cheapflightsfares deal was found by Cheapflights users on 3/31. 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 4/31:24 pmMKE - SJU
1 stop12h 16mSpirit Airlines
Mon 4/79:51 pmSJU - MKE
1 stop12h 18mSpirit Airlines
Deal found 3/31$292

Cheapflights Fare Finder

Customize your flight search to find flights from Wisconsin to Caribbean 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 1, 2025.
Use the filters below to find and compare flights from Wisconsin to Caribbean that are best for you.

Fly from

Wisconsin

Fly to

Caribbean

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

Wed 4/30

6:35 am-10:58 am

Nonstop5h 23m

$182

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Sat 5/3

1:33 pm-11:15 pm

1 stop8h 42m

San Juan Luis Munoz Marin Intl

Sat 5/10

6:15 am-1:54 pm

1 stop8h 39m

$215

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Sat 5/3

1:10 pm-11:57 pm

2 stops9h 47m

San Juan Luis Munoz Marin Intl

Sat 5/10

7:25 am-7:07 pm

2 stops12h 42m

$225

MinneapolisSan Juan

MSP - SJU

MSPSJU

Minneapolis St Paul

Mon 5/5

2:45 pm-10:32 am

1 stop18h 47m

San Juan Luis Munoz Marin Intl

Thu 5/8

12:36 pm-12:46 pm

2 stops25h 10m

$255

MinneapolisSan Juan

MSP - SJU

MSPSJU

Minneapolis St Paul

Sat 5/3

8:00 am-8:38 pm

1 stop11h 38m

San Juan Luis Munoz Marin Intl

Fri 5/9

1:05 am-11:22 am

1 stop11h 17m

$261

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 4/15

7:00 pm-8:26 am

1 stop12h 26m

San Juan Luis Munoz Marin Intl

Sun 4/20

5:55 am-3:06 pm

1 stop10h 11m

$264

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Sat 4/26

11:45 am-10:00 am

2 stops21h 15m

Saint Thomas Island Cyril E King

Sat 5/3

11:05 am-12:58 am

1 stop14h 53m

$265

MinneapolisSan Juan

MSP - SJU

MSPSJU

Minneapolis St Paul

Mon 4/14

6:00 am-8:26 am

2 stops25h 26m

San Juan Luis Munoz Marin Intl

Thu 4/17

5:10 pm-1:40 pm

2 stops21h 30m

$269

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Sat 5/3

6:40 am-12:09 am

1 stop16h 29m

San Juan Luis Munoz Marin Intl

Tue 5/6

6:10 am-5:36 pm

2 stops12h 26m

$285

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Thu 4/3

1:24 pm-2:40 am

1 stop12h 16m

San Juan Luis Munoz Marin Intl

Mon 4/7

3:00 am-5:37 pm

1 stop15h 37m

$287

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/30

Showing 1-10 of 60 results
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Best time to book a flight from Wisconsin to Caribbean

Have a flexible travel schedule? Discover the best time to fly to Caribbean 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

What is the cheapest month to book a flight from Wisconsin to Caribbean?

Currently, September is the cheapest month in which you can book a flight from Wisconsin to Caribbean (average of $254). Flying from Wisconsin to Caribbean 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 CB?

Find hourly flight availability from Wisconsin to Caribbean. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated April 1, 2025.

When flying from Wisconsin to Caribbean, 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 by month

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

In terms of precipitation, rainfall in Caribbean 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 when rainfall is around 2.2 in.

Temperature in Caribbean by month

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

If weather is an important factor for your trip to Caribbean, 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

Get insights into the airlines that provide service to Caribbean. 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. Reviews last updated April 1, 2025.
Delta
8.0
Very good
7,898 reviews

Overall

8.0

Crew

8.5

Entertainment

7.9

Food

7.3

Comfort

7.9

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
7,898 reviews
Delta
8.0
Very good
7,898 reviews

Overall

8.0

Crew

8.5

Entertainment

7.9

Food

7.3

Comfort

7.9

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
9,820 reviews
Delta
8.0
Very good
7,898 reviews

Overall

8.0

Crew

8.5

Entertainment

7.9

Food

7.3

Comfort

7.9

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
4,277 reviews
Delta
8.0
Very good
7,898 reviews

Overall

8.0

Crew

8.5

Entertainment

7.9

Food

7.3

Comfort

7.9

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
7.6
Good
1,400 reviews
Delta
8.0
Very good
7,898 reviews

Overall

8.0

Crew

8.5

Entertainment

7.9

Food

7.3

Comfort

7.9

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.
SWISS
7.5
Good
1,570 reviews
Delta
8.0
Very good
7,898 reviews

Overall

8.0

Crew

8.5

Entertainment

7.9

Food

7.3

Comfort

7.9

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. 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 one-way?

    For one-way options, check prices for Spirit Airlines. According to our data, you can fly for as low as $90. Users have also found prices from $108 and $114 on American Airlines and Sun Country Air, respectively.

  • Can I find deals for flights from Wisconsin to Caribbean that include hotel bookings?

    Yes. In addition to deals on Wisconsin to Caribbean flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Wisconsin to Caribbean?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Wisconsin to Caribbean.

  • Can I find deals for business class flights from Wisconsin to Caribbean?

    Yes. Cheapflights offers flight deals from Wisconsin to Caribbean 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?

    Currently, September is the cheapest month in which you can book a flight from Wisconsin to Caribbean (average of $254). Flying from Wisconsin to Caribbean 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

See prices for flight routes from nearby airports that may be better suited for you.
LaGuardia to Miami flights
Newark to Fort Lauderdale flights
Newark to Cancún flights
John F Kennedy Intl to Cancún flights
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LaGuardia to Orlando flights
John F Kennedy Intl to Charles de Gaulle flights
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Newark to Charles de Gaulle flights
Newark to Luis Munoz Marin Intl flights
John F Kennedy Intl to Leonardo da Vinci/Fiumicino flights
LaGuardia to Dallas/Fort Worth flights
John F Kennedy Intl to Fort Lauderdale flights
John F Kennedy Intl to Orlando flights
John F Kennedy Intl to Mexico City flights
Newark to Los Angeles flights
John F Kennedy Intl to Haneda flights
San Francisco to John F Kennedy Intl flights
John F Kennedy Intl to Gatwick flights
O'Hare Intl to Cancún flights
Los Angeles to Newark flights
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Los Angeles to Narita flights
Dallas/Fort Worth to O'Hare Intl flights
Newark to Seattle flights
Dallas/Fort Worth to Las Vegas flights
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Newark to Dallas/Fort Worth flights
LaGuardia to Atlanta flights
Denver to Las Vegas flights
O'Hare Intl to Las Vegas flights
Dulles Intl to Cancún flights
Newark to Narita flights
John F Kennedy Intl to Seattle flights
Newark to Tampa flights
John F Kennedy Intl to Luis Munoz Marin Intl flights
Dallas/Fort Worth to Newark flights
John F Kennedy Intl to San Francisco flights

Top 8 airlines flying from Wisconsin to Caribbean

Discover the top 8 airlines that operate flights from Wisconsin to Caribbean. 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 1, 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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