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$93+ 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 11/15. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SJU
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
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 September 15, 2025.

Round-trip from

$207
(Mytrip)

One-way from

$93
(Orbitz)

Popular in

June

Cheapest in

September

Average price

$317

Good round-trip deal

$841 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. 2% potential price decrease ($12 potential savings vs. average RT price).
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Average for round-trip flights in September 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 September 15, 2025.

This Mytrip deal was found by Cheapflights users on 9/14. 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 10/1111:55 amORD - SJU
2 stops26h 04mSpirit Airlines
Sat 10/189:48 amSJU - ORD
Nonstop5h 08mSpirit Airlines
Deal found 9/14$207
This Cheapflightsfares deal was found by Cheapflights users on 9/14. 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 10/249:06 pmORD - SJU
Nonstop4h 45mSpirit Airlines
Wed 10/293:19 pmSJU - ORD
1 stop7h 14mSpirit Airlines
Deal found 9/14$208
This Kiwi.com deal was found by Cheapflights users on 9/13. 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.
Sat 10/411:57 amORD - SJU
2 stops20h 59mMultiple Airlines
Tue 10/76:22 amSJU - ORD
1 stop11h 51mMultiple Airlines
Deal found 9/13$209
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
Mon 9/226:30 amORD - SJU
1 stop6h 41mSpirit Airlines
Thu 10/211:59 amSJU - ORD
1 stop6h 40mSpirit Airlines
Deal found 9/14$210
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
Mon 9/226:30 amORD - SJU
1 stop6h 41mSpirit Airlines
Sat 9/276:44 amSJU - ORD
1 stop10h 28mSpirit Airlines
Deal found 9/14$211
This Cheapflightsfares deal was found by Cheapflights users on 9/12. 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.
Wed 10/16:30 amORD - SJU
1 stop6h 41mSpirit Airlines
Sat 10/46:44 amSJU - ORD
1 stop10h 28mSpirit Airlines
Deal found 9/12$212
This Cheapflightsfares deal was found by Cheapflights users on 9/13. 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 10/35:17 pmORD - SJU
1 stop6h 37mSpirit Airlines
Sat 10/43:19 pmSJU - ORD
1 stop7h 39mSpirit Airlines
Deal found 9/13$213
This Cheapflightsfares deal was found by Cheapflights users on 9/14. 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.
Wed 12/36:55 amORD - SJU
Nonstop4h 38mSpirit Airlines
Mon 12/82:38 pmSJU - ORD
Nonstop5h 22mSpirit Airlines
Deal found 9/14$215
This Cheapflightsfares deal was found by Cheapflights users on 9/13. 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 12/67:35 amORD - SJU
1 stop11h 09mSpirit Airlines
Wed 12/172:38 pmSJU - ORD
Nonstop5h 22mSpirit Airlines
Deal found 9/13$216
This Cheapflightsfares deal was found by Cheapflights users on 9/14. 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 10/187:43 pmORD - SJU
1 stop14h 13mSpirit Airlines
Tue 10/213:19 pmSJU - ORD
1 stop7h 14mSpirit Airlines
Deal found 9/14$217
This United Airlines deal was found by Cheapflights users on 9/15. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/282:20 pmORD - SJU
Nonstop4h 40mUnited Airlines
Mon 11/38:10 amSJU - ORD
Nonstop5h 22mUnited Airlines
Deal found 9/15$218
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
Mon 10/279:06 pmORD - SJU
Nonstop4h 45mMultiple Airlines
Tue 11/49:00 amSJU - ORD
1 stop29h 45mMultiple Airlines
Deal found 9/14$219

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 September 15, 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

Fri 10/31

5:20 am-4:33 pm

1 stop10h 13m

San Juan Luis Munoz Marin Intl

Wed 11/5

7:00 am-5:22 pm

1 stop12h 22m

$227

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 10/21

7:00 am-4:25 pm

1 stop8h 25m

San Juan Luis Munoz Marin Intl

Sat 10/25

7:00 am-5:22 pm

1 stop11h 22m

$227

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Tue 10/28

6:05 am-2:40 pm

1 stop7h 35m

San Juan Luis Munoz Marin Intl

Mon 11/3

2:05 am-10:19 am

1 stop10h 14m

$235

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Thu 10/30

10:35 am-9:59 pm

1 stop10h 24m

San Juan Luis Munoz Marin Intl

Thu 11/6

7:15 am-4:19 pm

1 stop11h 04m

$235

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Tue 10/28

2:04 pm-9:59 pm

1 stop6h 55m

San Juan Luis Munoz Marin Intl

Thu 11/6

7:15 am-4:19 pm

1 stop11h 04m

$235

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 11/11

1:36 pm-12:36 am

1 stop9h 00m

San Juan Luis Munoz Marin Intl

Fri 11/14

2:05 am-10:45 am

1 stop10h 40m

$256

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Tue 10/14

9:30 am-9:56 am

2 stops23h 26m

Saint Thomas Island Cyril E King

Tue 10/21

11:01 am-6:38 pm

1 stop8h 37m

$288

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 10/21

1:17 pm-11:57 pm

1 stop9h 40m

San Juan Luis Munoz Marin Intl

Mon 10/27

1:05 am-9:02 am

1 stop8h 57m

$289

MinneapolisSan Juan

MSP - SJU

MSPSJU

Minneapolis St Paul

Sat 10/18

8:05 am-2:11 pm

Nonstop5h 06m

San Juan Luis Munoz Marin Intl

Fri 10/24

2:22 pm-8:34 pm

1 stop7h 12m

$301

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Tue 10/14

9:30 am-9:56 am

2 stops23h 26m

Saint Thomas Island Cyril E King

Mon 10/20

11:01 am-11:45 pm

1 stop13h 44m

$308

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

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 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 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 September 15, 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.

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.

  • How long is the flight from Wisconsin to Caribbean?

    Airlines like Delta, United Airlines, and Spirit Airlines fly from Wisconsin to Caribbean in about 7h 35m. The time it takes to get you to your destination can typically vary by up to 15h 51m. The distance between Wisconsin and Caribbean is about 2120 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines to fly from Wisconsin to Caribbean one-way?

    For one-way options, check prices for Arajet. According to our data, you can fly for as low as $93. Users have also found prices from $105 and $109 on Spirit Airlines and United Airlines, 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 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

Browse thousands of different options on Cheapflights for your next trip

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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.
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Top 7 airlines flying from Wisconsin to Caribbean

Discover the top 7 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 September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$129Average$230FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$208Average$391FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$215Average$672FlexibilityNo cancel feeOn-time69%
DeltaCheapest$215Average$673FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$274Average$674FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$315Average$750FlexibilityNo cancel feeOn-time63%
Sun Country AirCheapest$540Average$652FlexibilityNo cancel feeOn-time83%

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