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Wisconsin

$99+ Cheap flights from Caribbean Islands to Wisconsin

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 9/21. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — MKE
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
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Cheap flight deals from Caribbean Islands to Wisconsin

Keep the following information in mind while searching for Caribbean Islands to Wisconsin flight deals. Data was last updated September 15, 2025.

Round-trip from

$178
(Mytrip)

One-way from

$111
(Arajet)
From Caribbean Islands to Wisconsin
Search Deals
One-way flight from Caribbean Islands to Wisconsin
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Find flight deals from Caribbean Islands to Wisconsin

Cheapest flights from Caribbean Islands to Wisconsin
Explore the most affordable flight options available from Caribbean Islands to Wisconsin. 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 9/15. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/247:43 pmSJU - ORD
Nonstop5h 14mSpirit Airlines
Sat 10/253:00 pmORD - SJU
Nonstop4h 40mSpirit Airlines
Deal found 9/15$178
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.
Thu 10/211:59 amSJU - ORD
1 stop6h 40mSpirit Airlines
Mon 10/69:06 pmORD - SJU
Nonstop4h 45mSpirit Airlines
Deal found 9/14$186
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.
Fri 10/247:43 pmSJU - ORD
Nonstop5h 14mSpirit Airlines
Mon 10/279:06 pmORD - SJU
Nonstop4h 45mSpirit Airlines
Deal found 9/13$187
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/155:47 amPUJ - ORD
Nonstop5h 10mArajet
Sun 11/163:30 amORD - PUJ
Nonstop4h 45mArajet
Deal found 9/13$193
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/311:59 amSJU - ORD
1 stop11h 49mSpirit Airlines
Wed 10/86:00 amORD - SJU
1 stop7h 12mSpirit Airlines
Deal found 9/15$206
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.
Thu 10/1611:51 amSJU - ORD
1 stop7h 47mSpirit Airlines
Mon 10/209:06 pmORD - SJU
Nonstop4h 45mSpirit Airlines
Deal found 9/14$208
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/315:51 pmSJU - ORD
2 stops18h 39mFrontier
Sun 11/25:40 amORD - SJU
1 stop9h 14mFrontier
Deal found 9/14$209
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 10/33:19 pmSJU - ORD
1 stop7h 39mSpirit Airlines
Mon 10/69:06 pmORD - SJU
Nonstop4h 45mSpirit 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.
Fri 10/247:43 pmSJU - ORD
Nonstop5h 14mSpirit Airlines
Sat 11/12:03 pmORD - SJU
Nonstop4h 39mSpirit Airlines
Deal found 9/14$214
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.
Thu 12/42:38 pmSJU - ORD
Nonstop5h 22mSpirit Airlines
Mon 12/86:55 amORD - SJU
Nonstop4h 38mSpirit Airlines
Deal found 9/14$215
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.
Fri 10/247:43 pmSJU - ORD
Nonstop5h 14mMultiple Airlines
Wed 10/296:40 amORD - SJU
1 stop10h 14mMultiple Airlines
Deal found 9/14$217
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/257:30 pmPUJ - ORD
Nonstop5h 10mArajet
Sun 11/303:30 amORD - PUJ
Nonstop4h 45mArajet
Deal found 9/15$219

Cheapflights Fare Finder

 
Customize your flight search to find flights from Caribbean Islands to Wisconsin 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 Caribbean Islands to Wisconsin that are best for you.

Fly from

Caribbean Islands

Fly to

Wisconsin

Route

Depart

Return

Price

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Fri 10/24

3:19 pm-9:33 pm

1 stop7h 14m

Chicago O'Hare Intl

Mon 10/27

9:06 pm-2:51 am

Nonstop4h 45m

$208

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 10/23

4:55 pm-11:15 pm

1 stop7h 20m

Chicago O'Hare Intl

Sun 10/26

2:20 pm-8:00 pm

Nonstop4h 40m

$223

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Wed 10/22

1:05 am-8:38 am

1 stop8h 33m

Chicago O'Hare Intl

Wed 10/29

2:20 pm-8:00 pm

Nonstop4h 40m

$223

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Wed 10/22

1:05 am-8:38 am

1 stop8h 33m

Chicago O'Hare Intl

Mon 10/27

8:55 am-2:40 pm

Nonstop4h 45m

$223

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Wed 10/22

1:05 am-8:38 am

1 stop8h 33m

Chicago O'Hare Intl

Thu 10/30

2:20 pm-8:00 pm

Nonstop4h 40m

$223

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 10/23

12:11 pm-11:39 pm

2 stops12h 28m

Chicago O'Hare Intl

Thu 10/30

6:40 am-5:54 pm

1 stop10h 14m

$226

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Sat 10/25

7:00 am-5:22 pm

1 stop11h 22m

Chicago O'Hare Intl

Tue 10/28

5:20 am-4:33 pm

1 stop10h 13m

$227

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Fri 10/24

5:43 pm-11:58 pm

1 stop7h 15m

Chicago O'Hare Intl

Mon 10/27

7:00 am-4:25 pm

1 stop8h 25m

$227

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Wed 10/22

1:06 pm-8:07 pm

1 stop8h 01m

Milwaukee-Mitchell

Tue 10/28

7:00 am-4:25 pm

1 stop8h 25m

$235

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Sat 10/18

7:15 am-1:09 pm

1 stop6h 54m

Milwaukee-Mitchell

Tue 10/28

7:00 am-4:25 pm

1 stop8h 25m

$235

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/13

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

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

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

Currently, February is the cheapest month in which you can book a flight from Caribbean Islands to Wisconsin (average of $280). Flying from Caribbean Islands to Wisconsin in June is currently the most expensive (average of $376). 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 EPX to WI?

Find hourly flight availability from Caribbean Islands to Wisconsin. 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.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Caribbean Islands to Wisconsin as you normally would.

Reviews of airlines servicing Wisconsin

Get insights into the airlines that provide service to Wisconsin. 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 Wisconsin. Reviews last updated September 15, 2025.
Read through reviews of airlines operating flights from Caribbean Islands to Wisconsin, such as Delta, United Airlines, and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,954 reviews

Crew

8.5

Comfort

7.9

Overall

8.0

Entertainment

7.9

Boarding

8.2

Food

7.3

Reviews

1 / 20
6.0
Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others
Delta
8.0
Very good
7,954 reviews
Delta
8.0
Very good
7,954 reviews

Crew

8.5

Comfort

7.9

Overall

8.0

Entertainment

7.9

Boarding

8.2

Food

7.3

Reviews

1 / 20
6.0
Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others
United Airlines
7.4
Good
8,929 reviews
Delta
8.0
Very good
7,954 reviews

Crew

8.5

Comfort

7.9

Overall

8.0

Entertainment

7.9

Boarding

8.2

Food

7.3

Reviews

1 / 20
6.0
Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,954 reviews

Crew

8.5

Comfort

7.9

Overall

8.0

Entertainment

7.9

Boarding

8.2

Food

7.3

Reviews

1 / 20
6.0
Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others

Related info for your journey

Find useful and relevant information for your journey from Caribbean Islands to Wisconsin. 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 Caribbean Islands to Wisconsin?

    Spirit Airlines, United Airlines, and Delta can get you from Caribbean Islands to Wisconsin in just under 7h 14m. Your travel time can differ by up to 47m. Caribbean Islands and Wisconsin are separated by a distance of 2073 mi. This flight may include one or multiple stops.

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

    One-way options have recently been found by users for as low as $99 on Sun Country Air. Other airlines that offer cheap prices include Delta from $118 and American Airlines from $118 one-way.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Caribbean Islands to Wisconsin 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 Caribbean Islands to Wisconsin?

    Currently, February is the cheapest month in which you can book a flight from Caribbean Islands to Wisconsin (average of $280). Flying from Caribbean Islands to Wisconsin in June is currently the most expensive (average of $376). 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 Caribbean Islands to Wisconsin

See prices for flight routes from nearby airports that may be better suited for you.
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Top 4 airlines flying from Caribbean Islands to Wisconsin

Discover the top 4 airlines that operate flights from Caribbean Islands to Wisconsin. 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
United AirlinesCheapest$215Average$404FlexibilityNo cancel feeOn-time69%
DeltaCheapest$215Average$441FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$265Average$477FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$323Average$490FlexibilityNo cancel feeOn-time63%

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