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Wisconsin

$87+ 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 4/17. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — MKE
Apr 6 — Apr 131
Sun 4/6
Sun 4/13
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 1, 2025.

Round-trip from

$175
(Cheapflightsfares)

One-way from

$87
(FlightHub)

Popular in

June

Cheapest in

February

Average price

$406
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. 15% potential increase in price ($71 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($12 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 1, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 3/31. 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 4/246:35 amSJU - ORD
Nonstop5h 23mSpirit Airlines
Tue 4/297:00 pmORD - SJU
1 stop12h 26mSpirit Airlines
Deal found 3/31$175
This American Airlines deal was found by Cheapflights users on 4/1. 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.
Fri 4/256:05 amSJU - MKE
1 stop17h 53mAmerican Airlines
Sat 5/34:55 pmMKE - SJU
1 stop11h 05mAmerican Airlines
Deal found 4/1$215
This CheapOair deal was found by Cheapflights users on 4/1. 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.
Wed 4/165:03 pmPUJ - ORD
Nonstop5h 13mFrontier
Sun 4/206:00 amORD - PUJ
Nonstop4h 36mFrontier
Deal found 4/1$225
This Mytrip deal was found by Cheapflights users on 3/30. 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 4/2410:27 amSJU - MSP
1 stop28h 13mMultiple Airlines
Mon 4/288:20 amMSP - SJU
2 stops34h 20mMultiple Airlines
Deal found 3/30$239
This Mytrip deal was found by Cheapflights users on 3/30. 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 4/2410:27 amSJU - MSP
1 stop28h 13mSpirit Airlines
Mon 4/282:45 pmMSP - SJU
1 stop18h 47mSpirit Airlines
Deal found 3/30$241
This Priceline deal was found by Cheapflights users on 4/1. 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 5/612:00 pmMBJ - ORD
1 stop12h 20mSpirit Airlines
Tue 5/205:05 amORD - MBJ
1 stop5h 57mSpirit Airlines
Deal found 4/1$250
This United Airlines deal was found by Cheapflights users on 3/31. 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 3/31$253
This Mytrip deal was found by Cheapflights users on 4/1. 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 5/98:12 pmSJU - MKE
2 stops16h 15mSpirit Airlines
Fri 5/169:15 amMKE - SJU
1 stop12h 23mSpirit Airlines
Deal found 4/1$255
This Booking.com deal was found by Cheapflights users on 4/1. 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.
Wed 5/73:56 amSJU - ORD
1 stop20h 36mMultiple Airlines
Sun 5/1110:33 amORD - SJU
1 stop11h 20mMultiple Airlines
Deal found 4/1$271
This eDestinos deal was found by Cheapflights users on 4/1. 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 4/175:30 amSJU - ORD
1 stop10h 36mFrontier
Mon 4/219:50 amORD - SJU
1 stop22h 03mFrontier
Deal found 4/1$279
This CheapOair deal was found by Cheapflights users on 4/1. 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 5/812:42 pmPUJ - ORD
1 stop11h 47mMultiple Airlines
Sun 5/116:10 amORD - PUJ
Nonstop4h 41mMultiple Airlines
Deal found 4/1$281
This Cheapflightsfares deal was found by Cheapflights users on 3/31. 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.
Sat 4/264:05 pmSJU - MSP
Nonstop6h 11mSun Country Air
Sat 5/39:00 amMSP - SJU
Nonstop5h 11mSun Country Air
Deal found 3/31$291

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 1, 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

Thu 4/24

6:35 am-10:58 am

Nonstop5h 23m

Chicago O'Hare Intl

Tue 4/29

7:00 pm-8:26 am

1 stop12h 26m

$175

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Fri 4/25

6:05 am-10:58 pm

1 stop17h 53m

Milwaukee-Mitchell

Sat 5/3

4:55 pm-5:00 am

1 stop11h 05m

$215

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Wed 4/16

5:03 pm-9:16 pm

Nonstop5h 13m

Chicago O'Hare Intl

Sun 4/20

6:00 am-11:36 am

Nonstop4h 36m

$225

San JuanMinneapolis

SJU - MSP

SJUMSP

San Juan Luis Munoz Marin Intl

Thu 4/24

10:27 am-1:40 pm

1 stop28h 13m

Minneapolis St Paul

Mon 4/28

8:20 am-7:40 pm

2 stops34h 20m

$239

San JuanMinneapolis

SJU - MSP

SJUMSP

San Juan Luis Munoz Marin Intl

Thu 4/24

10:27 am-1:40 pm

1 stop28h 13m

Minneapolis St Paul

Mon 4/28

2:45 pm-10:32 am

1 stop18h 47m

$241

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Tue 5/6

12:00 pm-12:20 am

1 stop12h 20m

Chicago O'Hare Intl

Tue 5/20

5:05 am-11:02 am

1 stop5h 57m

$250

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Thu 5/1

1:50 pm-5:55 pm

Nonstop5h 05m

Chicago O'Hare Intl

Mon 5/5

9:23 am-3:05 pm

Nonstop4h 42m

$253

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Fri 5/9

8:12 pm-11:27 am

2 stops16h 15m

Milwaukee-Mitchell

Fri 5/16

9:15 am-10:38 pm

1 stop12h 23m

$255

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Wed 5/7

3:56 am-11:32 pm

1 stop20h 36m

Chicago O'Hare Intl

Sun 5/11

10:33 am-10:53 pm

1 stop11h 20m

$271

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 4/17

5:30 am-3:06 pm

1 stop10h 36m

Chicago O'Hare Intl

Mon 4/21

9:50 am-8:53 am

1 stop22h 03m

$279

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/31

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 1, 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 1, 2025.
Delta
8.0
Very good
7,898 reviews

Crew

8.5

Food

7.3

Entertainment

7.9

Comfort

7.9

Overall

8.0

Boarding

8.2

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
7,898 reviews
Delta
8.0
Very good
7,898 reviews

Crew

8.5

Food

7.3

Entertainment

7.9

Comfort

7.9

Overall

8.0

Boarding

8.2

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
9,820 reviews
Delta
8.0
Very good
7,898 reviews

Crew

8.5

Food

7.3

Entertainment

7.9

Comfort

7.9

Overall

8.0

Boarding

8.2

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
4,277 reviews
Delta
8.0
Very good
7,898 reviews

Crew

8.5

Food

7.3

Entertainment

7.9

Comfort

7.9

Overall

8.0

Boarding

8.2

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
1,400 reviews
Delta
8.0
Very good
7,898 reviews

Crew

8.5

Food

7.3

Entertainment

7.9

Comfort

7.9

Overall

8.0

Boarding

8.2

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
7,898 reviews

Crew

8.5

Food

7.3

Entertainment

7.9

Comfort

7.9

Overall

8.0

Boarding

8.2

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 $87. Users have also found prices from $108 and $118 on American Airlines and United Airlines, 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

Browse thousands of different options on Cheapflights for your next trip

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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 6 airlines flying from Caribbean to Wisconsin

Discover the top 6 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 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$182Average$345FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$215Average$506FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$265Average$501FlexibilityNo cancel feeOn-time71%
DeltaCheapest$275Average$476FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$378Average$481FlexibilityNo cancel feeOn-time63%
JetBlueCheapest$397Average$457FlexibilityNo cancel feeOn-time62%

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