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Caribbean Islands

$82+ 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 2/28. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SJU
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
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 January 29, 2026.

This Cheapflightsfares deal was found by Cheapflights users on 1/27. 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.
Tue 2/310:48 am
ORD
-
SJU
1 stop10h 45m
Spirit Airlines
Tue 2/101:22 pm
SJU
-
ORD
Nonstop5h 15m
Spirit Airlines
Deal found 1/27$185
This Priceline deal was found by Cheapflights users on 1/27. 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 3/312:17 pm
ORD
-
SJU
Nonstop4h 32m
Spirit Airlines
Sat 3/712:32 pm
SJU
-
ORD
Nonstop5h 16m
Spirit Airlines
Deal found 1/27$186
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 2/247:00 am
ORD
-
SJU
1 stop6h 31m
Spirit Airlines
Wed 3/1111:32 am
SJU
-
ORD
Nonstop5h 16m
Spirit Airlines
Deal found 1/27$187
This Kiwi.com deal was found by Cheapflights users on 1/28. 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 2/247:00 am
ORD
-
SJU
1 stop6h 31m
Multiple Airlines
Fri 3/66:50 pm
SJU
-
ORD
1 stop17h 03m
Multiple Airlines
Deal found 1/28$188
This Kiwi.com deal was found by Cheapflights users on 1/28. 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 2/247:00 am
ORD
-
SJU
1 stop6h 31m
Spirit Airlines
Thu 2/2612:32 pm
SJU
-
ORD
Nonstop5h 16m
Spirit Airlines
Deal found 1/28$189
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 2/233:50 pm
ORD
-
SJU
1 stop6h 53m
Multiple Airlines
Mon 3/911:32 am
SJU
-
ORD
Nonstop5h 16m
Multiple Airlines
Deal found 1/27$190
This JetBlue deal was found by Cheapflights users on 1/27. 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.
Mon 2/2310:00 am
ORD
-
SJU
1 stop10h 53m
JetBlue
Tue 2/245:10 am
SJU
-
ORD
1 stop8h 49m
JetBlue
Deal found 1/27$191
This Kiwi.com deal was found by Cheapflights users on 1/28. 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 4/205:01 am
ORD
-
SJU
1 stop8h 07m
Multiple Airlines
Sat 4/2512:22 pm
SJU
-
ORD
Nonstop5h 15m
Multiple Airlines
Deal found 1/28$192
This Mytrip deal was found by Cheapflights users on 1/29. 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.
Wed 3/1810:55 am
ORD
-
SJU
1 stop12h 03m
Spirit Airlines
Tue 3/2411:13 am
SJU
-
ORD
Nonstop5h 27m
Spirit Airlines
Deal found 1/29$193
This CheapOair deal was found by Cheapflights users on 1/28. 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 2/2412:50 pm
ORD
-
SJU
1 stop7h 41m
Multiple Airlines
Wed 3/45:45 pm
SJU
-
ORD
1 stop8h 55m
Multiple Airlines
Deal found 1/28$194
This Expedia deal was found by Cheapflights users on 1/27. 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.
Tue 4/147:26 pm
ORD
-
SJU
Nonstop4h 33m
Multiple Airlines
Tue 4/2111:59 pm
SJU
-
ORD
1 stop8h 42m
Multiple Airlines
Deal found 1/27$195
This CheapOair deal was found by Cheapflights users on 1/27. 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 4/114:21 pm
ORD
-
SJU
1 stop14h 35m
Multiple Airlines
Thu 4/1612:22 pm
SJU
-
ORD
Nonstop5h 15m
Multiple Airlines
Deal found 1/27$196

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 January 29, 2026.

Round-trip from

$185
(Expedia)

One-way from

$82
(Travelocity)

Popular in

December

Cheapest in

September

Average price

$401
From Wisconsin to Caribbean Islands
Search Deals
One-way flight from Wisconsin to Caribbean Islands
Search Deals
Highest demand for flights based on searches. 15% potential increase in price ($82 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($20 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
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 January 29, 2026.
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

Mon 5/11

3:15 pm-2:07 am

1 stop9h 52m

San Juan Luis Munoz Marin Intl

Wed 5/13

11:59 pm-9:48 am

1 stop10h 49m

$191

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 5/9

3:15 pm-2:07 am

1 stop9h 52m

San Juan Luis Munoz Marin Intl

Fri 5/15

11:59 pm-9:48 am

1 stop10h 49m

$192

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mon 3/9

12:41 pm-11:29 pm

1 stop9h 48m

San Juan Luis Munoz Marin Intl

Mon 3/16

3:26 am-11:25 am

1 stop8h 59m

$192

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 2/21

6:04 am-4:56 pm

1 stop8h 52m

San Juan Luis Munoz Marin Intl

Sat 2/28

5:10 am-12:04 pm

1 stop8h 54m

$215

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Fri 4/10

10:00 am-10:01 pm

1 stop11h 01m

San Juan Luis Munoz Marin Intl

Fri 4/17

11:59 pm-7:41 am

1 stop8h 42m

$215

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Thu 4/9

10:00 am-10:01 pm

1 stop11h 01m

San Juan Luis Munoz Marin Intl

Fri 4/17

11:59 pm-7:41 am

1 stop8h 42m

$215

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Thu 3/12

12:20 pm-8:26 pm

1 stop7h 06m

San Juan Luis Munoz Marin Intl

Mon 3/23

3:26 am-11:25 am

1 stop8h 59m

$221

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 3/10

12:39 pm-9:24 pm

1 stop7h 45m

San Juan Luis Munoz Marin Intl

Sat 3/14

2:30 am-10:10 am

1 stop8h 40m

$229

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 5/19

2:38 pm-8:34 pm

Nonstop4h 56m

San Juan Luis Munoz Marin Intl

Fri 5/29

7:40 am-11:53 am

Nonstop5h 13m

$237

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Thu 6/4

3:15 pm-12:59 am

1 stop8h 44m

San Juan Luis Munoz Marin Intl

Sun 6/7

12:30 pm-7:26 pm

1 stop7h 56m

$238

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/28

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 $378). 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 January 29, 2026.

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.

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 Southwest fly from Wisconsin to Caribbean Islands in about 9h 46m. The time it takes to get you to your destination can typically vary by up to 1h 14m. 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 $85. Users have also found prices from $108 and $108 on United Airlines and Delta, 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 $378). 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 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 January 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$85Average$291FlexibilityNo cancel feeOn-time62%
DeltaCheapest$118Average$679FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$158Average$630FlexibilityNo cancel feeOn-time69%
Spirit AirlinesCheapest$208Average$402FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$215Average$666FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$315Average$736FlexibilityNo cancel feeOn-time63%
Sun Country AirCheapest$497Average$652FlexibilityNo cancel feeOn-time83%

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