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Caribbean Islands

$98+ 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 1/18. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SJU
Jan 16 — Jan 231
Fri 1/16
Fri 1/23
1 adult, Economy
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Cheap 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 December 17, 2025.

This JetBlue deal was found by Cheapflights users on 12/17. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/266:45 amORD - SJU
1 stop10h 04mJetBlue
Sun 1/42:21 pmSJU - ORD
1 stop9h 43mJetBlue
Deal found 12/17$202
This Frontier deal was found by Cheapflights users on 12/15. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/312:15 pmORD - SJU
1 stop8h 14mFrontier
Thu 1/1511:55 amSJU - ORD
1 stop8h 30mFrontier
Deal found 12/15$205
This CheapOair deal was found by Cheapflights users on 12/17. 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.
Wed 12/315:45 amORD - SJU
Nonstop4h 41mSpirit Airlines
Thu 1/151:22 pmSJU - ORD
Nonstop5h 15mSpirit Airlines
Deal found 12/17$224
This Priceline deal was found by Cheapflights users on 12/16. 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 12/2512:39 pmORD - SJU
1 stop9h 58mMultiple Airlines
Fri 1/1611:06 amSJU - ORD
1 stop10h 30mMultiple Airlines
Deal found 12/16$227
This Priceline deal was found by Cheapflights users on 12/15. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/1611:25 amORD - SJU
1 stop10h 29mMultiple Airlines
Tue 12/238:08 pmSJU - ORD
Nonstop5h 17mMultiple Airlines
Deal found 12/15$230
This CheapOair deal was found by Cheapflights users on 12/16. 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 12/301:14 pmORD - SJU
1 stop7h 49mFrontier
Wed 1/77:18 pmSJU - ORD
1 stop25h 59mFrontier
Deal found 12/16$234
This American Airlines deal was found by Cheapflights users on 12/15. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/3110:25 pmORD - SJU
Nonstop4h 35mAmerican Airlines
Thu 1/156:00 amSJU - ORD
Nonstop5h 35mAmerican Airlines
Deal found 12/15$236
This Kiwi.com deal was found by Cheapflights users on 12/16. 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.
Wed 12/316:05 pmORD - SJU
1 stop12h 34mMultiple Airlines
Fri 1/910:47 pmSJU - ORD
1 stop11h 31mMultiple Airlines
Deal found 12/16$240
This Priceline deal was found by Cheapflights users on 12/15. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/1611:25 amORD - SJU
1 stop10h 29mMultiple Airlines
Mon 12/227:25 amSJU - ORD
1 stop13h 08mMultiple Airlines
Deal found 12/15$243
This Kiwi.com deal was found by Cheapflights users on 12/16. 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.
Tue 12/237:10 amORD - PUJ
Nonstop4h 37mFrontier
Tue 12/306:49 pmPUJ - ORD
Nonstop5h 10mFrontier
Deal found 12/16$290
This Kiwi.com deal was found by Cheapflights users on 12/16. 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.
Tue 12/237:10 amORD - PUJ
Nonstop4h 37mFrontier
Thu 12/256:49 pmPUJ - ORD
Nonstop5h 10mFrontier
Deal found 12/16$297
This Expedia deal was found by Cheapflights users on 12/16. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/315:45 amORD - PUJ
Nonstop4h 45mMultiple Airlines
Wed 1/76:08 pmPUJ - ORD
1 stop19h 14mMultiple Airlines
Deal found 12/16$302

Find 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 December 17, 2025.

Round-trip from

$194
(Kiwi.com)

One-way from

$98
(Kiwi.com)

Popular in

June

Cheapest in

September

Average price

$532
From Wisconsin to Caribbean Islands
Search Deals
One-way flight from Wisconsin to Caribbean Islands
Search Deals
Highest demand for flights based on searches. 9% potential increase in price ($48 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($12 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

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 December 17, 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

Thu 1/29

9:40 am-7:26 pm

1 stop7h 46m

San Juan Luis Munoz Marin Intl

Sat 2/7

1:30 pm-7:45 pm

1 stop8h 15m

$196

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Fri 2/27

12:41 pm-11:44 pm

1 stop9h 03m

San Juan Luis Munoz Marin Intl

Sat 3/7

5:10 am-11:58 am

1 stop8h 48m

$202

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 1/20

7:45 am-6:07 pm

1 stop8h 22m

San Juan Luis Munoz Marin Intl

Sat 1/24

10:25 am-7:36 pm

1 stop11h 11m

$205

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sun 1/18

7:45 am-6:05 pm

1 stop8h 20m

San Juan Luis Munoz Marin Intl

Fri 1/23

11:06 am-7:36 pm

1 stop10h 30m

$205

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 3/17

10:56 am-11:23 pm

1 stop11h 27m

San Juan Luis Munoz Marin Intl

Sun 3/22

1:30 am-10:05 am

1 stop9h 35m

$211

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Fri 2/6

7:45 am-6:02 pm

1 stop8h 17m

San Juan Luis Munoz Marin Intl

Sat 2/14

5:22 pm-11:10 pm

1 stop7h 48m

$211

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Fri 3/13

10:56 am-11:23 pm

1 stop11h 27m

San Juan Luis Munoz Marin Intl

Mon 3/23

1:30 am-10:05 am

1 stop9h 35m

$220

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Thu 1/15

5:15 am-4:37 pm

1 stop9h 22m

Saint Thomas Island Cyril E King

Sun 1/18

5:42 pm-11:46 pm

1 stop8h 04m

$321

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Tue 1/27

8:45 am-3:17 pm

Nonstop4h 32m

Punta Cana

Tue 2/3

4:25 pm-7:38 pm

Nonstop5h 13m

$351

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Fri 1/16

2:13 pm-2:05 am

1 stop9h 52m

Punta Cana

Tue 1/20

1:46 pm-12:24 am

1 stop12h 38m

$354

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/16

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, November is the cheapest month in which you can book a flight from Wisconsin to Caribbean Islands (average of $113). Flying from Wisconsin to Caribbean Islands 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 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 December 17, 2025.

Unlike in the morning, when flights are generally more expensive, you can save up to 20% on flights from Wisconsin to Caribbean Islands by exploring options for tickets at noon.

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

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

Travelers seeking maximum savings on their Wisconsin to Caribbean Islands 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 Islands. 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 Islands?

    Airlines like JetBlue, Spirit Airlines, and United Airlines fly from Wisconsin to Caribbean Islands in about 4h 32m. The time it takes to get you to your destination can typically vary by up to 4h 50m. The distance from Wisconsin to Caribbean Islands is about 1982 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

    For one-way options, check prices for Frontier. According to our data, you can fly for as low as $43. Users have also found prices from $108 and $108 on United Airlines and Southwest, 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, November is the cheapest month in which you can book a flight from Wisconsin to Caribbean Islands (average of $113). Flying from Wisconsin to Caribbean Islands 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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Top 7 airlines flying from Wisconsin to Caribbean Islands

Discover the top 7 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 December 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$129Average$256FlexibilityNo cancel feeOn-time62%
DeltaCheapest$191Average$673FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$215Average$671FlexibilityNo cancel feeOn-time69%
Spirit AirlinesCheapest$226Average$406FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$268Average$666FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$315Average$754FlexibilityNo cancel feeOn-time63%
Sun Country AirCheapest$497Average$652FlexibilityNo cancel feeOn-time83%

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