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$86+ 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 12/2. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SJU
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
1 adult, Economy
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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 October 30, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/204:51 pmORD - SJU
1 stop21h 37mMultiple Airlines
Mon 11/245:19 pmSJU - ORD
1 stop28h 02mMultiple Airlines
Deal found 10/30$210
This Priceline deal was found by Cheapflights users on 10/30. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/76:00 amORD - SJU
1 stop12h 08mMultiple Airlines
Fri 12/124:10 amSJU - ORD
1 stop8h 58mMultiple Airlines
Deal found 10/30$211
This Cheapflightsfares deal was found by Cheapflights users on 10/30. 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 11/165:10 amORD - SJU
1 stop10h 09mSpirit Airlines
Sat 11/224:12 pmSJU - ORD
Nonstop5h 11mSpirit Airlines
Deal found 10/30$212
This Mytrip deal was found by Cheapflights users on 10/30. 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.
Thu 11/278:41 amORD - SJU
Nonstop4h 36mMultiple Airlines
Thu 12/44:31 pmSJU - ORD
1 stop7h 53mMultiple Airlines
Deal found 10/30$213
This Priceline deal was found by Cheapflights users on 10/30. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/52:00 pmORD - SJU
1 stop18h 47mMultiple Airlines
Sun 12/78:45 pmSJU - ORD
Nonstop5h 14mMultiple Airlines
Deal found 10/30$214
This Frontier deal was found by Cheapflights users on 10/29. 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.
Mon 11/246:15 pmORD - SJU
1 stop6h 39mFrontier
Thu 11/274:05 pmSJU - ORD
1 stop10h 03mFrontier
Deal found 10/29$215
This Frontier deal was found by Cheapflights users on 10/30. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/117:40 amORD - SJU
1 stop10h 28mFrontier
Sat 12/204:02 pmSJU - ORD
1 stop8h 44mFrontier
Deal found 10/30$216
This Kiwi.com deal was found by Cheapflights users on 10/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/288:41 amORD - SJU
Nonstop4h 36mMultiple Airlines
Thu 12/410:42 amSJU - ORD
1 stop9h 54mMultiple Airlines
Deal found 10/30$217
This Priceline deal was found by Cheapflights users on 10/29. 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.
Thu 11/278:41 amORD - SJU
Nonstop4h 36mSpirit Airlines
Sat 12/67:31 pmSJU - ORD
Nonstop5h 22mSpirit Airlines
Deal found 10/29$218
This Mytrip deal was found by Cheapflights users on 10/29. 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.
Sun 12/76:00 amORD - SJU
1 stop12h 08mFrontier
Wed 12/104:31 pmSJU - ORD
1 stop26h 56mFrontier
Deal found 10/29$219
This Frontier deal was found by Cheapflights users on 10/29. 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 11/148:26 amORD - SJU
2 stops15h 06mFrontier
Sat 11/227:11 amSJU - ORD
1 stop12h 48mFrontier
Deal found 10/29$220
This Frontier deal was found by Cheapflights users on 10/30. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/76:00 amORD - SJU
1 stop12h 08mFrontier
Fri 12/123:55 amSJU - ORD
2 stops20h 29mFrontier
Deal found 10/30$221

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 October 30, 2025.

Round-trip from

$209
(Frontier)

One-way from

$86
(Priceline)

Popular in

June

Cheapest in

September

Average price

$338

Good round-trip deal

$767 or less
From Wisconsin to Caribbean
Search Deals
One-way flight from Wisconsin to Caribbean
Search Deals
Highest demand for flights based on searches. 11% potential increase in price ($53 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($14 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals
Price to beat on a round-trip flight from Wisconsin to Caribbean.
Search Deals

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 October 30, 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 2/8

2:20 pm-9:00 pm

Nonstop4h 40m

San Juan Luis Munoz Marin Intl

Fri 2/13

8:35 am-11:57 am

Nonstop5h 22m

$218

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mon 1/12

2:20 pm-9:00 pm

Nonstop4h 40m

San Juan Luis Munoz Marin Intl

Wed 2/4

2:05 am-10:53 am

1 stop10h 48m

$223

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Wed 1/21

2:20 pm-9:00 pm

Nonstop4h 40m

San Juan Luis Munoz Marin Intl

Wed 1/28

2:05 am-9:40 am

1 stop9h 35m

$223

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mon 1/19

2:49 pm-11:44 pm

1 stop6h 55m

San Juan Luis Munoz Marin Intl

Tue 2/3

7:00 am-5:45 pm

1 stop12h 45m

$227

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sun 1/18

5:33 am-5:17 pm

1 stop9h 44m

San Juan Luis Munoz Marin Intl

Fri 1/30

7:00 am-5:45 pm

1 stop12h 45m

$227

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Sun 1/25

10:13 am-11:44 pm

1 stop11h 31m

San Juan Luis Munoz Marin Intl

Wed 1/28

6:27 pm-11:46 pm

1 stop7h 19m

$235

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Tue 1/20

2:55 pm-11:44 pm

1 stop6h 49m

San Juan Luis Munoz Marin Intl

Thu 1/29

6:27 pm-11:46 pm

1 stop7h 19m

$235

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Fri 1/23

12:17 pm-11:44 pm

1 stop9h 27m

San Juan Luis Munoz Marin Intl

Thu 1/29

6:27 pm-11:46 pm

1 stop7h 19m

$235

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Tue 1/20

2:55 pm-11:44 pm

1 stop6h 49m

San Juan Luis Munoz Marin Intl

Fri 1/30

6:27 pm-11:46 pm

1 stop7h 19m

$235

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Sun 1/11

7:02 am-4:52 pm

1 stop7h 50m

San Juan Luis Munoz Marin Intl

Fri 1/23

6:15 am-11:10 am

1 stop6h 55m

$235

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/29

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, October is the cheapest month in which you can book a flight from Wisconsin to Caribbean (average of $143). Flying from Wisconsin to Caribbean in June is currently the most expensive (average of $379). 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 October 30, 2025.

It’s typically best to fly out from Wisconsin to Caribbean at noon. Doing so could potentially save you 20% on the flight price compared to flying in the morning, which is usually more expensive.

What is the cheapest day to fly from Wisconsin to Caribbean?

Use this chart to determine the cheapest time to fly round-trip from Wisconsin to Caribbean. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Wisconsin to Caribbean flight should consider departing on Sunday afternoons when fares are most often at their lowest. Monday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

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 United Airlines, Delta, and Sun Country Air fly from Wisconsin to Caribbean in about 4h 40m. The time it takes to get you to your destination can typically vary by up to 2h 15m. The distance between Wisconsin and Caribbean is about 2073 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 United Airlines. According to our data, you can fly for as low as $114. Users have also found prices from $116 and $117 on Sun Country Air and Arajet, 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, October is the cheapest month in which you can book a flight from Wisconsin to Caribbean (average of $143). Flying from Wisconsin to Caribbean in June is currently the most expensive (average of $379). 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.
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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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$129Average$243FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$202Average$670FlexibilityNo cancel feeOn-time69%
DeltaCheapest$215Average$644FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$226Average$409FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$269Average$672FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$315Average$755FlexibilityNo cancel feeOn-time63%
Sun Country AirCheapest$540Average$651FlexibilityNo cancel feeOn-time83%

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