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Wisconsin

$118+ Cheap flights from Caribbean 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 4/24. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — MKE
Apr 22 — Apr 291
Tue 4/22
Tue 4/29
1 adult, Economy
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Cheap flight deals from Caribbean to Wisconsin

Keep the following information in mind while searching for Caribbean to Wisconsin flight deals. Data was last updated April 17, 2025.

Round-trip from

$216
(eDestinos)

One-way from

$118
(eDestinos)

Popular in

June

Cheapest in

February

Average price

$359
From Caribbean to Wisconsin
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One-way flight from Caribbean to Wisconsin
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Highest demand for flights based on searches. 18% potential increase in price ($86 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($14 potential savings vs. average RT price).
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Average for round-trip flights in April 2025
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Find flight deals from Caribbean to Wisconsin

Cheapest flights from Caribbean to Wisconsin
Explore the most affordable flight options available from Caribbean to Wisconsin. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 17, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 4/17. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/259:30 pmSJU - ORD
1 stop11h 34mSpirit Airlines
Tue 4/297:00 pmORD - SJU
1 stop12h 26mSpirit Airlines
Deal found 4/17$208
This Cheapflightsfares deal was found by Cheapflights users on 4/17. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/15:54 pmPUJ - ORD
Nonstop5h 06mFrontier
Mon 5/56:10 amORD - PUJ
Nonstop4h 41mFrontier
Deal found 4/17$239
This CheapOair deal was found by Cheapflights users on 4/17. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/259:30 pmSJU - ORD
1 stop11h 34mMultiple Airlines
Sun 4/276:30 amORD - SJU
1 stop12h 11mMultiple Airlines
Deal found 4/17$248
This eDestinos deal was found by Cheapflights users on 4/17. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/91:59 amSJU - MKE
1 stop10h 28mSpirit Airlines
Tue 5/1312:22 pmMKE - SJU
1 stop11h 32mSpirit Airlines
Deal found 4/17$254
This Delta deal was found by Cheapflights users on 4/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/107:30 amSJU - MKE
1 stop9h 21mDelta
Tue 5/137:00 amMKE - SJU
1 stop8h 44mDelta
Deal found 4/17$265
This FlightHub deal was found by Cheapflights users on 4/16. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/71:34 pmKIN - ORD
2 stops19h 21mSpirit Airlines
Wed 5/145:05 amORD - KIN
1 stop7h 24mSpirit Airlines
Deal found 4/16$268
This Delta deal was found by Cheapflights users on 4/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/244:15 pmSJU - MSP
Nonstop5h 45mDelta
Sat 5/318:00 amMSP - SJU
1 stop10h 48mDelta
Deal found 4/17$277
This eDestinos deal was found by Cheapflights users on 4/17. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/216:00 pmSJU - ORD
1 stop15h 22mFrontier
Mon 5/265:14 pmORD - SJU
1 stop8h 18mFrontier
Deal found 4/17$288
This American Airlines deal was found by Cheapflights users on 4/16. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/72:12 pmPUJ - ORD
1 stop10h 59mAmerican Airlines
Sun 5/115:00 amORD - PUJ
1 stop7h 10mAmerican Airlines
Deal found 4/16$289
This Cheapflightsfares deal was found by Cheapflights users on 4/16. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/1012:07 pmMBJ - ORD
1 stop10h 57mSpirit Airlines
Wed 6/255:05 amORD - MBJ
1 stop5h 57mSpirit Airlines
Deal found 4/16$291
This Kiwi.com deal was found by Cheapflights users on 4/17. 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.
Thu 5/112:39 pmPUJ - ORD
1 stop11h 53mMultiple Airlines
Wed 5/77:25 amORD - PUJ
Nonstop4h 50mMultiple Airlines
Deal found 4/17$295
This American Airlines deal was found by Cheapflights users on 4/17. 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 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 stops13h 57mAmerican Airlines
Thu 9/184:41 pmMKE - SJU
2 stops17h 34mAmerican Airlines
Deal found 4/17$300

Cheapflights Fare Finder

Customize your flight search to find flights from Caribbean 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 17, 2025.
Use the filters below to find and compare flights from Caribbean to Wisconsin that are best for you.

Fly from

Caribbean

Fly to

Wisconsin

Route

Depart

Return

Price

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Fri 5/2

6:35 am-10:58 am

Nonstop5h 23m

Chicago O'Hare Intl

Mon 5/5

8:04 am-1:45 pm

Nonstop4h 41m

$216

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Thu 5/1

5:54 pm-10:00 pm

Nonstop5h 06m

Chicago O'Hare Intl

Mon 5/5

6:10 am-11:51 am

Nonstop4h 41m

$239

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Fri 5/9

1:59 am-11:27 am

1 stop10h 28m

Milwaukee-Mitchell

Tue 5/13

12:22 pm-12:54 am

1 stop11h 32m

$254

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Sat 5/10

7:30 am-3:51 pm

1 stop9h 21m

Milwaukee-Mitchell

Tue 5/13

7:00 am-4:44 pm

1 stop8h 44m

$265

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 5/8

3:56 am-11:32 pm

1 stop20h 36m

Chicago O'Hare Intl

Sun 5/11

4:15 pm-2:51 am

1 stop9h 36m

$270

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Mon 5/5

6:00 am-6:29 pm

1 stop13h 29m

Chicago O'Hare Intl

Mon 5/12

11:30 am-5:16 pm

Nonstop4h 46m

$275

San JuanMinneapolis

SJU - MSP

SJUMSP

San Juan Luis Munoz Marin Intl

Sat 5/24

4:15 pm-9:00 pm

Nonstop5h 45m

Minneapolis St Paul

Sat 5/31

8:00 am-7:48 pm

1 stop10h 48m

$277

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Fri 5/16

1:34 pm-12:05 am

1 stop10h 31m

Chicago O'Hare Intl

Tue 5/20

5:05 am-12:29 pm

1 stop7h 24m

$284

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Wed 5/7

2:12 pm-12:11 am

1 stop10h 59m

Chicago O'Hare Intl

Sun 5/11

5:00 am-1:10 pm

1 stop7h 10m

$289

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Tue 6/10

12:07 pm-11:04 pm

1 stop10h 57m

Chicago O'Hare Intl

Wed 6/25

5:05 am-11:02 am

1 stop5h 57m

$291

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/17

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

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

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

Currently, February is the cheapest month in which you can book a flight from Caribbean to Wisconsin (average of $280). Flying from Caribbean 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 CB to WI?

Find hourly flight availability from Caribbean 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 17, 2025.

When flying from Caribbean to Wisconsin, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 17, 2025.
Delta
8.0
Very good
7,916 reviews

Boarding

8.2

Comfort

7.9

Overall

8.0

Food

7.3

Crew

8.5

Entertainment

7.9

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
7,916 reviews
Delta
8.0
Very good
7,916 reviews

Boarding

8.2

Comfort

7.9

Overall

8.0

Food

7.3

Crew

8.5

Entertainment

7.9

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
9,887 reviews
Delta
8.0
Very good
7,916 reviews

Boarding

8.2

Comfort

7.9

Overall

8.0

Food

7.3

Crew

8.5

Entertainment

7.9

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
4,280 reviews
Delta
8.0
Very good
7,916 reviews

Boarding

8.2

Comfort

7.9

Overall

8.0

Food

7.3

Crew

8.5

Entertainment

7.9

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
1,409 reviews
Delta
8.0
Very good
7,916 reviews

Boarding

8.2

Comfort

7.9

Overall

8.0

Food

7.3

Crew

8.5

Entertainment

7.9

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
LATAM Airlines
7.5
Good
1,761 reviews
Delta
8.0
Very good
7,916 reviews

Boarding

8.2

Comfort

7.9

Overall

8.0

Food

7.3

Crew

8.5

Entertainment

7.9

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 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 to Wisconsin one-way?

    For one-way options, check prices for Spirit Airlines. According to our data, you can fly for as low as $118. Users have also found prices from $134 and $136 on American Airlines and Southwest, respectively.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Caribbean 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 to Wisconsin?

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

Discover the top 5 airlines that operate flights from Caribbean 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 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$182Average$373FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$215Average$506FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$265Average$491FlexibilityNo cancel feeOn-time71%
DeltaCheapest$275Average$477FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$323Average$481FlexibilityNo cancel feeOn-time63%

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