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Wisconsin

$105+ 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 12/9. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — MKE
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
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 October 30, 2025.

Round-trip from

$178
(Priceline)

One-way from

$105
(Priceline)
From Caribbean Islands to Wisconsin
Search Deals
One-way flight from Caribbean Islands to Wisconsin
Search Deals

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 October 30, 2025.

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.
Mon 12/88:45 pmSJU - ORD
Nonstop5h 14mMultiple Airlines
Fri 12/1212:15 pmORD - SJU
1 stop9h 41mMultiple Airlines
Deal found 10/30$178
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.
Sun 12/76:50 pmPUJ - ORD
Nonstop5h 10mFrontier
Sun 12/147:10 amORD - PUJ
Nonstop4h 37mFrontier
Deal found 10/30$179
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 12/56:50 pmPUJ - ORD
Nonstop5h 10mFrontier
Fri 12/127:10 amORD - PUJ
Nonstop4h 37mFrontier
Deal found 10/30$181
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/66:50 pmPUJ - ORD
Nonstop5h 10mFrontier
Tue 12/97:10 amORD - PUJ
Nonstop4h 37mFrontier
Deal found 10/30$183
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 12/48:45 pmSJU - ORD
Nonstop5h 14mMultiple Airlines
Mon 12/83:23 pmORD - SJU
1 stop7h 26mMultiple Airlines
Deal found 10/30$193
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.
Sat 12/66:50 pmPUJ - ORD
Nonstop5h 10mFrontier
Sat 12/137:10 amORD - PUJ
Nonstop4h 37mFrontier
Deal found 10/29$197
This CheapOair deal was found by Cheapflights users on 10/27. 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.
Thu 11/133:37 pmSJU - ORD
1 stop10h 50mSpirit Airlines
Sun 11/165:10 amORD - SJU
1 stop10h 09mSpirit Airlines
Deal found 10/27$203
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.
Tue 12/96:50 pmPUJ - ORD
Nonstop5h 10mFrontier
Tue 12/167:10 amORD - PUJ
Nonstop4h 37mFrontier
Deal found 10/29$214
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 12/54:10 amSJU - ORD
1 stop8h 58mMultiple Airlines
Sun 12/76:00 amORD - SJU
1 stop12h 08mMultiple Airlines
Deal found 10/30$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.
Fri 12/57:00 amSJU - ORD
2 stops15h 42mFrontier
Mon 12/83:23 pmORD - SJU
1 stop7h 26mFrontier
Deal found 10/30$216
This Cheapflightsfares deal was found by Cheapflights users on 10/28. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/49:00 amSJU - ORD
Nonstop5h 23mSpirit Airlines
Mon 12/85:45 amORD - SJU
Nonstop4h 41mSpirit Airlines
Deal found 10/28$217
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.
Thu 12/48:45 pmSJU - ORD
Nonstop5h 14mSpirit Airlines
Sun 12/75:40 amORD - SJU
Nonstop4h 41mSpirit Airlines
Deal found 10/30$218

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 October 30, 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 1/23

6:27 pm-11:57 pm

1 stop7h 30m

Chicago O'Hare Intl

Tue 2/3

7:01 am-4:52 pm

1 stop7h 51m

$227

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Fri 12/5

6:38 pm-12:01 am

1 stop7h 23m

Chicago O'Hare Intl

Mon 12/8

5:30 am-2:14 pm

1 stop6h 44m

$227

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Thu 2/19

6:49 pm-9:59 pm

Nonstop5h 10m

Chicago O'Hare Intl

Mon 2/23

7:00 am-1:37 pm

Nonstop4h 37m

$233

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Sat 2/14

5:47 am-8:57 am

Nonstop5h 10m

Chicago O'Hare Intl

Sat 2/21

10:27 am-5:12 pm

Nonstop4h 45m

$243

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Sat 2/7

5:47 am-8:57 am

Nonstop5h 10m

Chicago O'Hare Intl

Sat 2/14

10:27 am-5:12 pm

Nonstop4h 45m

$243

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Sat 4/25

5:47 am-9:57 am

Nonstop5h 10m

Chicago O'Hare Intl

Sat 5/2

11:27 am-5:12 pm

Nonstop4h 45m

$243

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Sun 12/7

6:00 am-8:09 pm

1 stop16h 09m

Chicago O'Hare Intl

Mon 12/8

5:40 am-12:21 pm

Nonstop4h 41m

$251

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Thu 2/19

11:05 am-6:45 pm

1 stop9h 40m

Milwaukee-Mitchell

Mon 2/23

7:40 pm-9:55 am

1 stop12h 15m

$281

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Mon 1/26

8:40 am-11:35 pm

2 stops16h 55m

Chicago O'Hare Intl

Sun 2/1

5:20 am-3:06 pm

1 stop7h 46m

$292

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Fri 12/5

2:55 pm-6:08 pm

Nonstop5h 13m

Chicago O'Hare Intl

Fri 12/12

9:30 am-4:02 pm

Nonstop4h 32m

$307

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/28

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 $290). 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 October 30, 2025.

Unlike at noon, when flights are generally more expensive, you can save up to 20% 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 October 30, 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
7,998 reviews

Comfort

7.9

Entertainment

7.9

Crew

8.5

Overall

7.9

Boarding

8.2

Food

7.3

Reviews

1 / 20
10.0
Excellent

Mary,Oct 2025

AMS - PDX

It's specail being able to fly non-stop from Amsterdam all the way home to Portland, Oregon!
Delta
7.9
Good
7,998 reviews
Delta
7.9
Good
7,998 reviews

Comfort

7.9

Entertainment

7.9

Crew

8.5

Overall

7.9

Boarding

8.2

Food

7.3

Reviews

1 / 20
10.0
Excellent

Mary,Oct 2025

AMS - PDX

It's specail being able to fly non-stop from Amsterdam all the way home to Portland, Oregon!
United Airlines
7.4
Good
8,998 reviews
Delta
7.9
Good
7,998 reviews

Comfort

7.9

Entertainment

7.9

Crew

8.5

Overall

7.9

Boarding

8.2

Food

7.3

Reviews

1 / 20
10.0
Excellent

Mary,Oct 2025

AMS - PDX

It's specail being able to fly non-stop from Amsterdam all the way home to Portland, Oregon!
American Airlines
7.2
Good
11,035 reviews
Delta
7.9
Good
7,998 reviews

Comfort

7.9

Entertainment

7.9

Crew

8.5

Overall

7.9

Boarding

8.2

Food

7.3

Reviews

1 / 20
10.0
Excellent

Mary,Oct 2025

AMS - PDX

It's specail being able to fly non-stop from Amsterdam all the way home to Portland, Oregon!

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?

    Delta, Frontier, and Arajet can get you from Caribbean Islands to Wisconsin in just under 5h 10m. Your travel time can differ by up to 2h 20m. Caribbean Islands and Wisconsin are separated by a distance of 1982 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 $109 on United Airlines. Other airlines that offer cheap prices include Delta from $118 and Spirit Airlines from $131 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 $290). 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 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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$215Average$399FlexibilityNo cancel feeOn-time69%
DeltaCheapest$215Average$441FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$235Average$456FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$305Average$485FlexibilityNo cancel feeOn-time63%

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