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Wisconsin

$92+ 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 2/18. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — MKE
Jan 16 — Jan 231
Fri 1/16
Fri 1/23
1 adult, Economy
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Cheap 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 December 17, 2025.

This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/238:08 pmSJU - ORD
Nonstop5h 17mMultiple Airlines
Mon 1/51:44 pmORD - SJU
1 stop9h 22mMultiple Airlines
Deal found 12/16$184
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.
Thu 12/256:28 pmSJU - ORD
1 stop8h 02mMultiple Airlines
Sat 1/108:27 pmORD - SJU
1 stop10h 27mMultiple Airlines
Deal found 12/16$185
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 12/248:08 pmSJU - ORD
Nonstop5h 17mMultiple Airlines
Thu 1/88:27 pmORD - SJU
1 stop10h 27mMultiple Airlines
Deal found 12/16$186
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/228:08 pmSJU - ORD
Nonstop5h 17mSpirit Airlines
Mon 1/55:45 amORD - SJU
Nonstop4h 41mSpirit Airlines
Deal found 12/15$187
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.
Thu 12/256:28 pmSJU - ORD
1 stop8h 02mMultiple Airlines
Tue 1/65:00 amORD - SJU
1 stop16h 44mMultiple Airlines
Deal found 12/16$188
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/234:19 pmSJU - ORD
1 stop8h 05mFrontier
Thu 1/83:32 pmORD - SJU
1 stop7h 27mFrontier
Deal found 12/16$192
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/228:08 pmSJU - ORD
Nonstop5h 17mMultiple Airlines
Thu 1/16:00 amORD - SJU
1 stop7h 01mMultiple Airlines
Deal found 12/15$193
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/248:08 pmSJU - ORD
Nonstop5h 17mMultiple Airlines
Thu 1/112:39 pmORD - SJU
1 stop9h 58mMultiple Airlines
Deal found 12/17$196
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 12/236:25 amSJU - ORD
1 stop7h 40mMultiple Airlines
Fri 1/912:17 pmORD - SJU
Nonstop4h 32mMultiple Airlines
Deal found 12/16$198
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 12/248:08 pmSJU - ORD
Nonstop5h 17mSpirit Airlines
Fri 1/912:17 pmORD - SJU
Nonstop4h 32mSpirit Airlines
Deal found 12/16$199
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 12/2411:57 amSJU - ORD
1 stop10h 09mMultiple Airlines
Wed 1/79:34 amORD - SJU
1 stop7h 21mMultiple Airlines
Deal found 12/16$200
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 12/236:49 pmPUJ - ORD
Nonstop5h 10mFrontier
Tue 12/307:10 amORD - PUJ
Nonstop4h 37mFrontier
Deal found 12/16$204

Find 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 December 17, 2025.

Round-trip from

$169
(CheapOair)

One-way from

$92
(Priceline)
From Caribbean Islands to Wisconsin
Search Deals
One-way flight from Caribbean Islands to Wisconsin
Search Deals

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 December 17, 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

Thu 2/5

11:06 am-7:31 pm

1 stop10h 25m

Chicago O'Hare Intl

Sun 2/8

7:45 am-6:02 pm

1 stop8h 17m

$179

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Tue 4/7

1:00 pm-9:33 pm

1 stop9h 33m

Chicago O'Hare Intl

Tue 4/14

1:45 pm-1:47 am

1 stop11h 02m

$211

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Wed 2/25

8:35 am-11:57 am

Nonstop5h 22m

Chicago O'Hare Intl

Mon 3/9

2:20 pm-8:00 pm

Nonstop4h 40m

$216

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Tue 3/24

1:30 am-10:05 am

1 stop9h 35m

Chicago O'Hare Intl

Sun 3/29

10:56 am-11:23 pm

1 stop11h 27m

$220

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 1/22

1:22 pm-4:37 pm

Nonstop5h 15m

Chicago O'Hare Intl

Thu 1/29

12:17 pm-6:49 pm

Nonstop4h 32m

$222

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Thu 3/5

2:47 pm-10:53 pm

1 stop10h 06m

Milwaukee-Mitchell

Sun 3/8

6:22 am-10:31 pm

1 stop15h 09m

$235

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Thu 2/12

2:16 pm-8:36 pm

1 stop8h 20m

Milwaukee-Mitchell

Mon 2/16

12:20 pm-11:58 pm

1 stop9h 38m

$235

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Thu 1/29

7:07 am-9:59 pm

1 stop16h 52m

Milwaukee-Mitchell

Mon 2/2

6:12 am-8:50 pm

1 stop12h 38m

$239

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Wed 5/13

12:30 pm-7:26 pm

1 stop7h 56m

Chicago O'Hare Intl

Tue 5/26

3:15 pm-1:59 am

1 stop9h 44m

$248

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Wed 1/21

4:52 pm-8:20 pm

Nonstop5h 28m

Chicago O'Hare Intl

Sat 1/24

2:20 pm-9:00 pm

Nonstop4h 40m

$256

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 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, September is the cheapest month in which you can book a flight from Caribbean Islands to Wisconsin (average of $113). Flying from Caribbean Islands to Wisconsin in July is currently the most expensive (average of $289). 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 December 17, 2025.

Unlike in the afternoon, when flights are generally more expensive, you can save up to 21% on flights from Caribbean Islands to Wisconsin by exploring options for tickets in the evening.

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

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

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

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 December 17, 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
7.9
Good
8,008 reviews

Crew

8.5

Food

7.3

Overall

7.9

Comfort

7.9

Boarding

8.1

Entertainment

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Delta
7.9
Good
8,008 reviews
Delta
7.9
Good
8,008 reviews

Crew

8.5

Food

7.3

Overall

7.9

Comfort

7.9

Boarding

8.1

Entertainment

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
United Airlines
7.4
Good
9,092 reviews
Delta
7.9
Good
8,008 reviews

Crew

8.5

Food

7.3

Overall

7.9

Comfort

7.9

Boarding

8.1

Entertainment

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
American Airlines
7.2
Good
11,049 reviews
Delta
7.9
Good
8,008 reviews

Crew

8.5

Food

7.3

Overall

7.9

Comfort

7.9

Boarding

8.1

Entertainment

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

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?

    JetBlue, United Airlines, and American Airlines can get you from Caribbean Islands to Wisconsin in just under 5h 22m. Your travel time can differ by up to 5h 03m. 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 $64 on Frontier. Other airlines that offer cheap prices include United Airlines from $112 and Southwest from $112 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, September is the cheapest month in which you can book a flight from Caribbean Islands to Wisconsin (average of $113). Flying from Caribbean Islands to Wisconsin in July is currently the most expensive (average of $289). 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 Caribbean Islands to Wisconsin

See prices for flight routes from nearby airports that may be better suited for you.
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Top 5 airlines flying from Caribbean Islands to Wisconsin

Discover the top 5 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 December 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$118Average$462FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$182Average$315FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$215Average$402FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$235Average$471FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$305Average$485FlexibilityNo cancel feeOn-time63%

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