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Wisconsin

$118+ 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 4/26. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — MKE
Apr 29 — May 61
Tue 4/29
Tue 5/6
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 April 24, 2025.

Round-trip from

$188
(eDestinos)

One-way from

$119
(eDestinos)
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 April 24, 2025.

This eDestinos deal was found by Cheapflights users on 4/23. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/96:09 amSJU - ORD
Nonstop5h 16mSpirit Airlines
Fri 5/94:35 pmORD - SJU
1 stop17h 10mSpirit Airlines
Deal found 4/23$188
This CheapOair deal was found by Cheapflights users on 4/23. 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 5/85:54 pmPUJ - ORD
Nonstop5h 06mFrontier
Sun 5/116:10 amORD - PUJ
Nonstop4h 41mFrontier
Deal found 4/23$226
This CheapOair deal was found by Cheapflights users on 4/23. 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.
Fri 5/210:46 amSJU - ORD
1 stop13h 25mMultiple Airlines
Sat 5/104:35 pmORD - SJU
1 stop17h 10mMultiple Airlines
Deal found 4/23$238
This Delta deal was found by Cheapflights users on 4/23. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/412:56 pmSJU - MKE
1 stop11h 29mDelta
Thu 9/186:00 amMKE - SJU
1 stop9h 08mDelta
Deal found 4/23$256
This Booking.com deal was found by Cheapflights users on 4/22. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/85:54 pmPUJ - ORD
Nonstop5h 06mMultiple Airlines
Sun 5/115:05 amORD - PUJ
1 stop8h 12mMultiple Airlines
Deal found 4/22$270
This eDestinos deal was found by Cheapflights users on 4/23. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/81:59 amSJU - MKE
2 stops8h 41mSpirit Airlines
Mon 5/1210:35 amMKE - SJU
2 stops13h 19mSpirit Airlines
Deal found 4/23$275
This American Airlines deal was found by Cheapflights users on 4/23. 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 7/94:55 pmPUJ - ORD
1 stop8h 02mAmerican Airlines
Wed 8/67:00 amORD - PUJ
1 stop6h 45mAmerican Airlines
Deal found 4/23$296
This Frontier deal was found by Cheapflights users on 4/23. 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 5/210:46 amSJU - ORD
1 stop13h 25mFrontier
Mon 5/56:55 amORD - SJU
1 stop10h 52mFrontier
Deal found 4/23$296
This American Airlines deal was found by Cheapflights users on 4/23. 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.
Thu 9/48:30 amSJU - MKE
2 stops15h 59mAmerican Airlines
Thu 9/184:41 pmMKE - SJU
2 stops17h 34mAmerican Airlines
Deal found 4/23$299
This Delta deal was found by Cheapflights users on 4/23. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/307:30 amSJU - ORD
1 stop10h 16mDelta
Wed 9/31:31 pmORD - SJU
1 stop9h 15mDelta
Deal found 4/23$307
This eDestinos deal was found by Cheapflights users on 4/23. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/214:20 pmSJU - MSP
Nonstop5h 37mSun Country Air
Sat 6/289:00 amMSP - SJU
Nonstop5h 16mSun Country Air
Deal found 4/23$308
This United Airlines deal was found by Cheapflights users on 4/22. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/11:50 pmPUJ - ORD
Nonstop5h 05mUnited Airlines
Mon 5/59:23 amORD - PUJ
Nonstop4h 42mUnited Airlines
Deal found 4/22$310

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 April 24, 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 5/9

8:12 pm-8:50 am

1 stop13h 38m

Chicago O'Hare Intl

Sun 5/11

11:30 am-5:16 pm

Nonstop4h 46m

$188

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Wed 5/14

5:54 pm-10:00 pm

Nonstop5h 06m

Chicago O'Hare Intl

Wed 5/21

7:25 am-1:15 pm

Nonstop4h 50m

$226

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Fri 5/2

10:46 am-11:11 pm

1 stop13h 25m

Chicago O'Hare Intl

Sat 5/10

4:35 pm-10:45 am

1 stop17h 10m

$243

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Thu 9/4

12:56 pm-11:25 pm

1 stop11h 29m

Milwaukee-Mitchell

Thu 9/18

6:00 am-4:08 pm

1 stop9h 08m

$256

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Thu 5/8

1:59 am-9:40 am

2 stops8h 41m

Milwaukee-Mitchell

Mon 5/12

10:35 am-12:54 am

2 stops13h 19m

$275

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Thu 5/8

5:54 pm-10:00 pm

Nonstop5h 06m

Chicago O'Hare Intl

Sun 5/11

5:05 am-2:17 pm

1 stop8h 12m

$291

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Wed 7/9

4:55 pm-11:57 pm

1 stop8h 02m

Chicago O'Hare Intl

Wed 8/6

7:00 am-2:45 pm

1 stop6h 45m

$296

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Fri 5/2

10:46 am-11:11 pm

1 stop13h 25m

Chicago O'Hare Intl

Mon 5/5

4:15 pm-12:05 am

1 stop6h 50m

$298

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Thu 9/4

8:30 am-11:29 pm

2 stops15h 59m

Milwaukee-Mitchell

Thu 9/18

4:41 pm-11:15 am

2 stops17h 34m

$299

San JuanMinneapolis

SJU - MSP

SJUMSP

San Juan Luis Munoz Marin Intl

Sat 6/21

4:20 pm-8:57 pm

Nonstop5h 37m

Minneapolis St Paul

Sat 6/28

9:00 am-3:16 pm

Nonstop5h 16m

$308

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/22

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 April 24, 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.

Rainfall in Wisconsin by month

Plan your trip to Wisconsin by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Wisconsin ranges from 1.4 - 4.0 inches per month. June is typically the wettest month, when rainfall can reach 4.0 in. January is typically the driest time to visit Wisconsin when rainfall is around 1.4 in.

Temperature in Wisconsin by month

Plan your trip to Wisconsin by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Wisconsin, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 21.2 F).

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 April 24, 2025.
Read reviews from past customers who have flown Delta, Alaska Airlines and Southwest from Caribbean Islands to Wisconsin. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,920 reviews

Entertainment

7.9

Food

7.3

Boarding

8.2

Comfort

7.9

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Delta
8.0
Very good
7,920 reviews
Delta
8.0
Very good
7,920 reviews

Entertainment

7.9

Food

7.3

Boarding

8.2

Comfort

7.9

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Alaska Airlines
8.0
Very good
9,918 reviews
Delta
8.0
Very good
7,920 reviews

Entertainment

7.9

Food

7.3

Boarding

8.2

Comfort

7.9

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Southwest
8.0
Very good
4,286 reviews
Delta
8.0
Very good
7,920 reviews

Entertainment

7.9

Food

7.3

Boarding

8.2

Comfort

7.9

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Copa Airlines
7.6
Good
1,411 reviews
Delta
8.0
Very good
7,920 reviews

Entertainment

7.9

Food

7.3

Boarding

8.2

Comfort

7.9

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Aeromexico
7.5
Good
1,700 reviews
Delta
8.0
Very good
7,920 reviews

Entertainment

7.9

Food

7.3

Boarding

8.2

Comfort

7.9

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

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.

  • 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 $119 on Spirit Airlines. Other airlines that offer cheap prices include Sun Country Air from $132 and Frontier from $135 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 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 April 24, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$182Average$345FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$215Average$517FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$265Average$529FlexibilityNo cancel feeOn-time71%
DeltaCheapest$275Average$477FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$323Average$481FlexibilityNo cancel feeOn-time63%

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