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Wisconsin

$92+ 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 2/18. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — MKE
Jan 20 — Jan 271
Tue 1/20
Tue 1/27
1 adult, Economy
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Cheap 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 December 21, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 12/19. 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 12/256:28 pmSJU - ORD
1 stop8h 02mSpirit Airlines
Thu 1/17:20 amORD - SJU
1 stop16h 52mSpirit Airlines
Deal found 12/19$186
This Kiwi.com deal was found by Cheapflights users on 12/18. 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.
Tue 12/236:49 pmPUJ - ORD
Nonstop5h 10mFrontier
Tue 12/307:10 amORD - PUJ
Nonstop4h 37mFrontier
Deal found 12/18$190
This Priceline deal was found by Cheapflights users on 12/19. 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.
Wed 12/317:30 amSJU - ORD
1 stop13h 03mFrontier
Mon 1/51:44 pmORD - SJU
1 stop9h 22mFrontier
Deal found 12/19$192
This Kiwi.com deal was found by Cheapflights users on 12/18. 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 12/256:28 pmSJU - ORD
1 stop8h 02mMultiple Airlines
Thu 1/112:39 pmORD - SJU
1 stop9h 58mMultiple Airlines
Deal found 12/18$195
This Kiwi.com deal was found by Cheapflights users on 12/20. 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.
Wed 12/246:28 pmSJU - ORD
1 stop8h 02mMultiple Airlines
Wed 12/312:15 pmORD - SJU
1 stop8h 14mMultiple Airlines
Deal found 12/20$198
This Kiwi.com deal was found by Cheapflights users on 12/20. 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.
Wed 12/2411:38 amSJU - ORD
1 stop9h 24mSpirit Airlines
Thu 1/17:20 amORD - SJU
1 stop16h 52mSpirit Airlines
Deal found 12/20$199
This eDestinos deal was found by Cheapflights users on 12/20. 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 12/256:28 pmSJU - ORD
1 stop8h 02mSpirit Airlines
Mon 1/55:45 amORD - SJU
Nonstop4h 41mSpirit Airlines
Deal found 12/20$201
This Frontier deal was found by Cheapflights users on 12/18. 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.
Thu 12/254:21 pmSJU - ORD
1 stop8h 03mFrontier
Thu 1/112:39 pmORD - SJU
1 stop9h 58mFrontier
Deal found 12/18$204
This eDestinos deal was found by Cheapflights users on 12/18. 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.
Mon 12/2910:33 amSJU - ORD
1 stop24h 29mFrontier
Fri 1/25:15 amORD - SJU
1 stop17h 14mFrontier
Deal found 12/18$206
This Kiwi.com deal was found by Cheapflights users on 12/18. 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 12/216:28 pmSJU - ORD
1 stop8h 02mMultiple Airlines
Thu 1/112:39 pmORD - SJU
1 stop9h 58mMultiple Airlines
Deal found 12/18$207
This eDestinos deal was found by Cheapflights users on 12/19. 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.
Mon 12/295:22 pmSJU - ORD
1 stop16h 59mFrontier
Mon 1/51:44 pmORD - SJU
1 stop25h 13mFrontier
Deal found 12/19$209
This Super.com deal was found by Cheapflights users on 12/19. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/256:49 pmPUJ - ORD
Nonstop5h 10mFrontier
Thu 1/17:10 amORD - PUJ
Nonstop4h 37mFrontier
Deal found 12/19$242

Find flight deals from Caribbean to Wisconsin

Keep the following information in mind while searching for Caribbean to Wisconsin flight deals. Data was last updated December 21, 2025.

Round-trip from

$177
(CheapOair)

One-way from

$92
(Priceline)

Popular in

July

Cheapest in

February

Average price

$360
From Caribbean to Wisconsin
Search Deals
One-way flight from Caribbean to Wisconsin
Search Deals
Highest demand for flights based on searches. 22% potential increase in price ($108 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($11 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

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 December 21, 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 2/5

11:06 am-7:31 pm

1 stop10h 25m

Chicago O'Hare Intl

Mon 2/9

7:45 am-6:02 pm

1 stop8h 17m

$179

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Fri 1/23

11:06 am-7:36 pm

1 stop10h 30m

Chicago O'Hare Intl

Mon 1/26

9:40 am-7:26 pm

1 stop7h 46m

$182

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Thu 1/22

8:00 am-6:16 pm

1 stop12h 16m

Milwaukee-Mitchell

Sun 1/25

6:51 pm-6:40 pm

1 stop21h 49m

$215

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Wed 2/25

8:30 am-11:52 am

Nonstop5h 22m

Chicago O'Hare Intl

Mon 3/2

8:55 am-3:40 pm

Nonstop4h 45m

$216

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 1/22

11:06 am-7:36 pm

1 stop10h 30m

Chicago O'Hare Intl

Thu 1/29

9:40 am-7:26 pm

1 stop7h 46m

$231

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Fri 2/13

6:15 am-11:13 am

1 stop6h 58m

Milwaukee-Mitchell

Mon 2/16

12:20 pm-9:12 pm

1 stop6h 52m

$235

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Thu 3/5

12:31 pm-10:53 pm

1 stop12h 22m

Milwaukee-Mitchell

Sun 3/8

6:37 pm-10:40 am

1 stop15h 03m

$235

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Wed 1/21

4:36 pm-6:16 pm

1 stop27h 40m

Milwaukee-Mitchell

Sun 1/25

6:51 pm-6:40 pm

1 stop21h 49m

$236

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Thu 1/22

6:00 am-6:26 pm

1 stop14h 26m

Milwaukee-Mitchell

Sun 1/25

6:00 am-8:50 pm

2 stops12h 50m

$239

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Thu 1/29

2:28 pm-8:24 pm

1 stop7h 56m

Milwaukee-Mitchell

Mon 2/2

1:04 pm-9:39 pm

1 stop6h 35m

$239

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/19

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, September is the cheapest month in which you can book a flight from Caribbean to Wisconsin (average of $113). Flying from Caribbean to Wisconsin in July is currently the most expensive (average of $289). 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 December 21, 2025.

It’s typically best to fly out from Caribbean to Wisconsin in the evening. Doing so could potentially save you 21% on the flight price compared to flying in the afternoon, which is usually more expensive.

What is the cheapest day to fly from Caribbean to Wisconsin?

Use this chart to determine the cheapest time to fly round-trip from Caribbean to Wisconsin. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Caribbean 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 December 21, 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
4,257 reviews

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.5

Overall

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
8.0
Very good
4,257 reviews
Southwest
8.0
Very good
4,257 reviews

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.5

Overall

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Delta
7.9
Good
8,021 reviews
Southwest
8.0
Very good
4,257 reviews

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.5

Overall

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
United Airlines
7.4
Good
9,100 reviews
Southwest
8.0
Very good
4,257 reviews

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.5

Overall

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
American Airlines
7.2
Good
11,050 reviews
Southwest
8.0
Very good
4,257 reviews

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.5

Overall

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Spirit Airlines
6.3
Okay
8,194 reviews
Southwest
8.0
Very good
4,257 reviews

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.5

Overall

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

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 JetBlue, Frontier, and United Airlines fly from Caribbean to Wisconsin in about 5h 22m. The time it takes to get you to your destination can typically vary by up to 6h 54m. 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 Frontier. According to our data, you can fly for as low as $64. Users have also found prices from $112 and $112 on United 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, September is the cheapest month in which you can book a flight from Caribbean to Wisconsin (average of $113). Flying from Caribbean to Wisconsin in July is currently the most expensive (average of $289). 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 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 December 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$118Average$462FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$182Average$315FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$215Average$402FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$235Average$471FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$305Average$485FlexibilityNo cancel feeOn-time63%

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