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Wisconsin

$76+ 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 5/7. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — MKE
Feb 26 — Mar 51
Wed 2/26
Wed 3/5
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 February 21, 2025.

Round-trip from

$137
(Kiwi.com)

One-way from

$76
(Mytrip)

Popular in

June

Cheapest in

February

Average price

$303
From Caribbean to Wisconsin
Search Deals
One-way flight from Caribbean to Wisconsin
Search Deals
Highest demand for flights based on searches. 15% potential increase in price ($73 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 February 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 February 21, 2025.

This Kiwi.com deal was found by Cheapflights users on 2/20. 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.
Thu 4/246:35 amSJU - ORD
Nonstop5h 23mMultiple Airlines
Mon 4/284:30 pmORD - SJU
1 stop9h 19mMultiple Airlines
Deal found 2/20$137
This eDestinos deal was found by Cheapflights users on 2/20. 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.
Tue 3/113:38 amSJU - ORD
1 stop7h 01mSpirit Airlines
Mon 3/178:46 pmORD - SJU
Nonstop4h 41mSpirit Airlines
Deal found 2/20$138
This Flightnetwork deal was found by Cheapflights users on 2/20. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/111:20 amSJU - ORD
1 stop20h 46mFrontier
Mon 5/54:15 pmORD - SJU
1 stop9h 36mFrontier
Deal found 2/20$148
This Frontier deal was found by Cheapflights users on 2/20. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/102:54 amSJU - MKE
1 stop10h 25mFrontier
Thu 3/271:19 pmMKE - SJU
1 stop11h 30mFrontier
Deal found 2/20$151
This Mytrip deal was found by Cheapflights users on 2/20. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/1112:05 pmSJU - MKE
2 stops29h 34mSpirit Airlines
Thu 3/2710:14 amMKE - SJU
1 stop14h 22mSpirit Airlines
Deal found 2/20$193
This Mytrip deal was found by Cheapflights users on 2/20. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/23:05 amSJU - MKE
1 stop10h 24mMultiple Airlines
Mon 4/76:32 pmMKE - SJU
1 stop21h 49mMultiple Airlines
Deal found 2/20$194
This FlightHub deal was found by Cheapflights users on 2/20. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/29:51 pmSJU - MSP
2 stops17h 27mSpirit Airlines
Tue 4/84:27 pmMSP - SJU
1 stop16h 13mSpirit Airlines
Deal found 2/20$207
This OneTravel deal was found by Cheapflights users on 2/20. 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 OneTravel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/73:44 amSJU - MSP
1 stop7h 55mMultiple Airlines
Sat 4/51:45 pmMSP - SJU
1 stop18h 41mMultiple Airlines
Deal found 2/20$212
This Frontier deal was found by Cheapflights users on 2/20. 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 Frontier 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 35mFrontier
Deal found 2/20$220
This American Airlines deal was found by Cheapflights users on 2/20. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/265:00 amSJU - MSP
1 stop9h 12mAmerican Airlines
Sun 3/306:19 amMSP - SJU
1 stop15h 31mAmerican Airlines
Deal found 2/20$261
This eDestinos deal was found by Cheapflights users on 2/19. 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.
Fri 2/283:00 pmSJU - MSP
Nonstop6h 10mSun Country Air
Sun 3/26:40 amMSP - SJU
Nonstop5h 11mSun Country Air
Deal found 2/19$264
This Delta deal was found by Cheapflights users on 2/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/264:15 pmSJU - ORD
1 stop9h 34mDelta
Sun 3/211:15 amORD - SJU
1 stop10h 31mDelta
Deal found 2/20$271

Find flights from Caribbean to Wisconsin within your budget

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 February 21, 2025.

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

Mon 4/28

4:30 pm-2:49 am

1 stop9h 19m

$137

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Tue 3/11

3:38 am-9:39 am

1 stop7h 01m

Chicago O'Hare Intl

Mon 3/17

8:46 pm-2:27 am

Nonstop4h 41m

$138

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 5/1

11:20 am-7:06 am

1 stop20h 46m

Chicago O'Hare Intl

Mon 5/5

4:15 pm-2:51 am

1 stop9h 36m

$148

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Mon 3/10

2:54 am-12:19 pm

1 stop10h 25m

Milwaukee-Mitchell

Thu 3/27

1:19 pm-1:49 am

1 stop11h 30m

$151

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Tue 3/11

12:05 pm-4:39 pm

2 stops29h 34m

Milwaukee-Mitchell

Thu 3/27

10:14 am-1:36 am

1 stop14h 22m

$193

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Wed 4/2

3:05 am-12:29 pm

1 stop10h 24m

Milwaukee-Mitchell

Mon 4/7

6:32 pm-5:21 pm

1 stop21h 49m

$194

San JuanMinneapolis

SJU - MSP

SJUMSP

San Juan Luis Munoz Marin Intl

Wed 4/2

9:51 pm-2:18 pm

2 stops17h 27m

Minneapolis St Paul

Tue 4/8

4:27 pm-9:40 am

1 stop16h 13m

$207

San JuanMinneapolis

SJU - MSP

SJUMSP

San Juan Luis Munoz Marin Intl

Fri 3/7

3:44 am-9:39 am

1 stop7h 55m

Minneapolis St Paul

Sat 4/5

1:45 pm-9:26 am

1 stop18h 41m

$212

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-11:45 am

Nonstop4h 35m

$220

San JuanMinneapolis

SJU - MSP

SJUMSP

San Juan Luis Munoz Marin Intl

Wed 3/26

5:00 am-1:12 pm

1 stop9h 12m

Minneapolis St Paul

Sun 3/30

6:19 am-10:50 pm

1 stop15h 31m

$261

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/20

Showing 1-10 of 60 results
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2
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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.

Travel insights for flights from Caribbean to Wisconsin

Get recent, data-driven insights about flights from Caribbean to Wisconsin including ideal travel times, pricing trends, and more.

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 February 21, 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 February 21, 2025.
Southwest
8.1
Very good
4,401 reviews

Entertainment

7.6

Boarding

8.2

Food

7.1

Comfort

8.1

Overall

8.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Southwest
8.1
Very good
4,401 reviews
Southwest
8.1
Very good
4,401 reviews

Entertainment

7.6

Boarding

8.2

Food

7.1

Comfort

8.1

Overall

8.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Delta
8.0
Very good
8,213 reviews
Southwest
8.1
Very good
4,401 reviews

Entertainment

7.6

Boarding

8.2

Food

7.1

Comfort

8.1

Overall

8.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Alaska Airlines
8.0
Very good
9,697 reviews
Southwest
8.1
Very good
4,401 reviews

Entertainment

7.6

Boarding

8.2

Food

7.1

Comfort

8.1

Overall

8.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Copa Airlines
7.6
Good
1,510 reviews
Southwest
8.1
Very good
4,401 reviews

Entertainment

7.6

Boarding

8.2

Food

7.1

Comfort

8.1

Overall

8.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

LATAM Airlines
7.5
Good
1,793 reviews
Southwest
8.1
Very good
4,401 reviews

Entertainment

7.6

Boarding

8.2

Food

7.1

Comfort

8.1

Overall

8.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

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 $76. Users have also found prices from $79 and $131 on Frontier and American 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

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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 February 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$265Average$500FlexibilityNo cancel feeOn-time71%
DeltaCheapest$308Average$485FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$341Average$592FlexibilityNo cancel feeOn-time69%
JetBlueCheapest$370Average$434FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$378Average$478FlexibilityNo cancel feeOn-time63%
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