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Wisconsin

$109+ 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 11/15. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — MKE
Oct 16 — Oct 231
Thu 10/16
Thu 10/23
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 September 16, 2025.

Round-trip from

$178
(Mytrip)

One-way from

$109
(Mytrip)

Popular in

July

Cheapest in

February

Average price

$328
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. 21% potential increase in price ($104 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($11 potential savings vs. average RT price).
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Average for round-trip flights in September 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 September 16, 2025.

This Mytrip deal was found by Cheapflights users on 9/15. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/247:43 pmSJU - ORD
Nonstop5h 14mSpirit Airlines
Sat 10/253:00 pmORD - SJU
Nonstop4h 40mSpirit Airlines
Deal found 9/15$178
This Cheapflightsfares deal was found by Cheapflights users on 9/14. 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 10/211:59 amSJU - ORD
1 stop6h 40mSpirit Airlines
Mon 10/69:06 pmORD - SJU
Nonstop4h 45mSpirit Airlines
Deal found 9/14$186
This Kiwi.com deal was found by Cheapflights users on 9/13. 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 10/247:43 pmSJU - ORD
Nonstop5h 14mSpirit Airlines
Mon 10/279:06 pmORD - SJU
Nonstop4h 45mSpirit Airlines
Deal found 9/13$187
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 10/247:43 pmSJU - ORD
Nonstop5h 14mSpirit Airlines
Fri 10/319:06 pmORD - SJU
Nonstop4h 45mSpirit Airlines
Deal found 9/14$192
This Cheapflightsfares deal was found by Cheapflights users on 9/15. 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.
Fri 10/311:59 amSJU - ORD
1 stop11h 49mSpirit Airlines
Wed 10/86:00 amORD - SJU
1 stop7h 12mSpirit Airlines
Deal found 9/15$206
This Cheapflightsfares deal was found by Cheapflights users on 9/14. 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 10/1611:51 amSJU - ORD
1 stop7h 47mSpirit Airlines
Mon 10/209:06 pmORD - SJU
Nonstop4h 45mSpirit Airlines
Deal found 9/14$208
This Frontier deal was found by Cheapflights users on 9/14. 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 10/315:51 pmSJU - ORD
2 stops18h 39mFrontier
Sun 11/25:40 amORD - SJU
1 stop9h 14mFrontier
Deal found 9/14$209
This Cheapflightsfares deal was found by Cheapflights users on 9/14. 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 10/33:19 pmSJU - ORD
1 stop7h 39mSpirit Airlines
Mon 10/69:06 pmORD - SJU
Nonstop4h 45mSpirit Airlines
Deal found 9/14$210
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 10/247:43 pmSJU - ORD
Nonstop5h 14mSpirit Airlines
Sat 11/12:03 pmORD - SJU
Nonstop4h 39mSpirit Airlines
Deal found 9/14$214
This Cheapflightsfares deal was found by Cheapflights users on 9/13. 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 11/132:38 pmSJU - ORD
Nonstop5h 22mSpirit Airlines
Mon 11/176:55 amORD - SJU
Nonstop4h 38mSpirit Airlines
Deal found 9/13$215
This Expedia deal was found by Cheapflights users on 9/16. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/257:30 pmPUJ - ORD
Nonstop5h 10mArajet
Tue 12/24:35 amORD - PUJ
Nonstop4h 45mArajet
Deal found 9/16$216
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 10/247:43 pmSJU - ORD
Nonstop5h 14mMultiple Airlines
Tue 10/286:40 amORD - SJU
1 stop10h 14mMultiple Airlines
Deal found 9/14$217

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 September 16, 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 10/23

4:55 pm-11:15 pm

1 stop7h 20m

Chicago O'Hare Intl

Sun 10/26

2:20 pm-8:00 pm

Nonstop4h 40m

$223

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Tue 11/4

3:46 pm-11:10 pm

1 stop9h 24m

Chicago O'Hare Intl

Sun 11/9

2:20 pm-9:00 pm

Nonstop4h 40m

$223

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Wed 10/22

1:05 am-8:38 am

1 stop8h 33m

Chicago O'Hare Intl

Thu 10/30

2:20 pm-8:00 pm

Nonstop4h 40m

$223

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 10/30

5:50 am-12:45 pm

1 stop7h 55m

Chicago O'Hare Intl

Mon 11/3

6:05 am-11:20 pm

2 stops15h 15m

$227

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Wed 10/22

1:06 pm-9:39 pm

1 stop9h 33m

Chicago O'Hare Intl

Wed 10/29

7:00 am-4:25 pm

1 stop8h 25m

$227

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Sat 10/25

7:00 am-5:22 pm

1 stop11h 22m

Chicago O'Hare Intl

Fri 10/31

5:20 am-4:33 pm

1 stop10h 13m

$227

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Fri 11/14

6:40 am-2:45 pm

1 stop10h 05m

Chicago O'Hare Intl

Mon 11/17

3:45 pm-12:35 am

1 stop6h 50m

$227

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Thu 10/2

12:10 pm-10:48 pm

1 stop10h 38m

Chicago O'Hare Intl

Sun 10/5

7:43 pm-11:00 am

1 stop15h 17m

$234

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Wed 10/22

1:06 pm-8:07 pm

1 stop8h 01m

Milwaukee-Mitchell

Tue 10/28

7:00 am-4:25 pm

1 stop8h 25m

$235

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Wed 10/22

1:06 pm-8:07 pm

1 stop8h 01m

Milwaukee-Mitchell

Fri 10/24

2:04 pm-9:59 pm

1 stop6h 55m

$235

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

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 September 16, 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.

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 September 16, 2025.
Get a feel of what it's like to fly with Southwest, Delta, and United Airlines from Caribbean to Wisconsin by reading reviews from past customers. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,242 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Overall

8.0

Food

7.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Overall

8.0

Food

7.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Delta
8.0
Very good
7,957 reviews
Southwest
8.0
Very good
4,242 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Overall

8.0

Food

7.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
8,924 reviews
Southwest
8.0
Very good
4,242 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Overall

8.0

Food

7.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,242 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Overall

8.0

Food

7.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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.

  • How long is the flight from Caribbean to Wisconsin?

    Airlines like United Airlines, Southwest, and Delta fly from Caribbean to Wisconsin in about 7h 20m. The time it takes to get you to your destination can typically vary by up to 2h 13m. There are 2073 mi between Caribbean and Wisconsin. This flight may include one or multiple stops.

  • What are the cheapest airlines to fly from Caribbean to Wisconsin one-way?

    For one-way options, check prices for Delta. According to our data, you can fly for as low as $118. Users have also found prices from $118 and $134 on United Airlines and Arajet, 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 4 airlines flying from Caribbean to Wisconsin

Discover the top 4 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 September 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$215Average$404FlexibilityNo cancel feeOn-time69%
DeltaCheapest$215Average$441FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$265Average$477FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$323Average$490FlexibilityNo cancel feeOn-time63%

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