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Wisconsin

$108+ 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 10/4. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — MKE
août 5 — août 121
mar. 8/5
mar. 8/12
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 juillet 31, 2025.

Round-trip from

$215
(Southwest)

One-way from

$108
(American Airlines)

Popular in

July

Cheapest in

February

Average price

$494
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. 16% potential increase in price ($72 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 July 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 juillet 31, 2025.

This Southwest deal was found by Cheapflights users on 7/31. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 9/184:05 pmSJU - MKE
1 stop7h 55mSouthwest
dim. 9/285:45 amMKE - SJU
1 stop6h 30mSouthwest
Deal found 7/31$215
This American Airlines deal was found by Cheapflights users on 7/29. 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.
mer. 9/104:43 pmSJU - MKE
2 stops18h 21mAmerican Airlines
dim. 9/146:23 pmMKE - SJU
2 stops17h 24mAmerican Airlines
Deal found 7/29$220
This FlightHub deal was found by Cheapflights users on 7/31. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ven. 8/1510:16 pmSJU - ORD
1 stop12h 06mSpirit Airlines
lun. 8/1812:55 pmORD - SJU
Nonstop4h 45mSpirit Airlines
Deal found 7/31$221
This Delta deal was found by Cheapflights users on 7/29. 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.
jeu. 11/66:43 pmSJU - MKE
1 stop7h 12mDelta
mar. 11/117:00 amMKE - SJU
1 stop8h 10mDelta
Deal found 7/29$225
This KAYAK deal was found by Cheapflights users on 7/29. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 10/73:00 pmSJU - ORD
Nonstop5h 20mAmerican Airlines
mer. 10/87:11 amORD - SJU
2 stops15h 48mAmerican Airlines
Deal found 7/29$230
This Cheapflightsfares deal was found by Cheapflights users on 7/31. 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.
jeu. 9/182:48 pmSJU - MSP
1 stop8h 20mSpirit Airlines
dim. 9/215:15 amMSP - SJU
1 stop7h 38mSpirit Airlines
Deal found 7/31$238
This Expedia deal was found by Cheapflights users on 7/30. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mer. 8/133:29 amSJU - ORD
1 stop12h 58mMultiple Airlines
dim. 8/176:56 amORD - SJU
1 stop7h 14mMultiple Airlines
Deal found 7/30$242
This Mytrip deal was found by Cheapflights users on 7/30. 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.
mar. 8/123:40 amSJU - ORD
1 stop7h 34mFrontier
sam. 9/138:00 amORD - SJU
1 stop14h 59mFrontier
Deal found 7/30$248
This Frontier deal was found by Cheapflights users on 7/30. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ven. 9/193:32 amBQN - ORD
1 stop12h 45mFrontier
ven. 10/38:49 pmORD - BQN
1 stop13h 07mFrontier
Deal found 7/30$258
This Priceline deal was found by Cheapflights users on 7/31. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mer. 9/35:05 pmSDQ - ORD
1 stop7h 54mSpirit Airlines
sam. 9/205:05 amORD - SDQ
1 stop8h 37mSpirit Airlines
Deal found 7/31$262
This SmartFares deal was found by Cheapflights users on 7/30. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 8/144:12 pmSJU - MSP
1 stop28h 44mMultiple Airlines
sam. 8/239:22 amMSP - SJU
2 stops27h 55mMultiple Airlines
Deal found 7/30$271
This CheapOair deal was found by Cheapflights users on 7/29. 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.
mer. 8/134:05 pmSJU - MKE
1 stop8h 01mSpirit Airlines
dim. 8/176:00 amMKE - SJU
1 stop8h 10mSpirit Airlines
Deal found 7/29$273

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 juillet 31, 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 JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

jeu. 9/18

4:05 pm-11:00 pm

1 stop7h 55m

Milwaukee-Mitchell

dim. 9/28

5:45 am-1:15 pm

1 stop6h 30m

$215

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

mer. 9/10

4:43 pm-10:04 am

2 stops18h 21m

Milwaukee-Mitchell

dim. 9/14

6:23 pm-12:47 pm

2 stops17h 24m

$220

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

ven. 8/15

10:16 pm-9:22 am

1 stop12h 06m

Chicago O'Hare Intl

lun. 8/18

12:55 pm-6:40 pm

Nonstop4h 45m

$221

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

mar. 10/7

3:00 pm-7:20 pm

Nonstop5h 20m

Chicago O'Hare Intl

mer. 10/8

7:11 am-11:59 pm

2 stops15h 48m

$230

San JuanMinneapolis

SJU - MSP

SJUMSP

San Juan Luis Munoz Marin Intl

jeu. 9/18

2:48 pm-10:08 pm

1 stop8h 20m

Minneapolis St Paul

dim. 9/21

5:15 am-1:53 pm

1 stop7h 38m

$238

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

mer. 8/13

3:29 am-3:27 pm

1 stop12h 58m

Chicago O'Hare Intl

dim. 8/17

6:56 am-3:10 pm

1 stop7h 14m

$242

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

mar. 8/12

3:40 am-10:14 am

1 stop7h 34m

Chicago O'Hare Intl

sam. 9/13

8:00 am-8:02 am

1 stop23h 02m

$248

AguadillaChicago

BQN - ORD

BQNORD

Aguadilla Borinquen

ven. 9/19

3:32 am-3:17 pm

1 stop12h 45m

Chicago O'Hare Intl

ven. 10/3

8:49 pm-10:56 am

1 stop13h 07m

$258

Santo DomingoChicago

SDQ - ORD

SDQORD

Santo Domingo Las Americas

mer. 9/3

5:05 pm-11:59 pm

1 stop7h 54m

Chicago O'Hare Intl

sam. 9/20

5:05 am-2:42 pm

1 stop8h 37m

$262

San JuanMinneapolis

SJU - MSP

SJUMSP

San Juan Luis Munoz Marin Intl

jeu. 8/14

4:12 pm-7:56 pm

1 stop28h 44m

Minneapolis St Paul

sam. 8/23

9:22 am-2:17 pm

2 stops27h 55m

$271

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/30

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 juillet 31, 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 juillet 31, 2025.
Get a feel of what it's like to fly with Southwest, Delta, and Copa 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
4,246 reviews

Crew

8.6

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Food

7.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Crew

8.6

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Food

7.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Delta
8.0
Very good
7,981 reviews
Southwest
8.0
Very good
4,246 reviews

Crew

8.6

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Food

7.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Copa Airlines
7.5
Good
1,493 reviews
Southwest
8.0
Very good
4,246 reviews

Crew

8.6

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Food

7.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
United Airlines
7.4
Good
8,900 reviews
Southwest
8.0
Very good
4,246 reviews

Crew

8.6

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Food

7.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,246 reviews

Crew

8.6

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Food

7.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

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 American Airlines. According to our data, you can fly for as low as $108. Users have also found prices from $113 and $113 on Delta and Spirit 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

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 juillet 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$215Average$419FlexibilityNo cancel feeOn-time69%
DeltaCheapest$265Average$437FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$265Average$486FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$323Average$485FlexibilityNo cancel feeOn-time63%

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