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Wisconsin

$108+ Cheap flights from Caribbean Islands 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 9/19. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — MKE
Aug 2 — Aug 91
Sat 8/2
Sat 8/9
1 adult, Economy
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Cheap flight deals from Caribbean Islands to Wisconsin

Keep the following information in mind while searching for Caribbean Islands to Wisconsin flight deals. Data was last updated July 28, 2025.

Round-trip from

$215
(American Airlines)

One-way from

$108
(Delta)
From Caribbean Islands to Wisconsin
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One-way flight from Caribbean Islands to Wisconsin
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Find flight deals from Caribbean Islands to Wisconsin

Cheapest flights from Caribbean Islands to Wisconsin
Explore the most affordable flight options available from Caribbean Islands to Wisconsin. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 28, 2025.

This American Airlines deal was found by Cheapflights users on 7/26. 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 9/104:43 pmSJU - MKE
2 stops18h 21mAmerican Airlines
Sun 9/146:23 pmMKE - SJU
2 stops17h 24mAmerican Airlines
Deal found 7/26$215
This eDestinos deal was found by Cheapflights users on 7/26. 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 8/86:00 amSJU - ORD
Nonstop5h 16mSpirit Airlines
Sat 8/166:56 amORD - SJU
1 stop16h 01mSpirit Airlines
Deal found 7/26$231
This CheapOair deal was found by Cheapflights users on 7/28. 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.
Sat 8/164:54 pmSJU - ORD
1 stop24h 44mMultiple Airlines
Sat 8/2312:55 pmORD - SJU
Nonstop4h 45mMultiple Airlines
Deal found 7/28$232
This Delta deal was found by Cheapflights users on 7/26. 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.
Thu 12/42:26 pmSJU - MKE
1 stop7h 41mDelta
Wed 12/107:00 amMKE - SJU
1 stop8h 10mDelta
Deal found 7/26$245
This eDestinos deal was found by Cheapflights users on 7/27. 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 8/2812:59 amSJU - ORD
1 stop12h 21mFrontier
Mon 9/15:10 amORD - SJU
1 stop8h 16mFrontier
Deal found 7/27$252
This CheapOair deal was found by Cheapflights users on 7/28. 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 9/31:59 amSJU - MKE
1 stop10h 59mSpirit Airlines
Thu 9/1812:53 pmMKE - SJU
1 stop10h 51mSpirit Airlines
Deal found 7/28$255
This Frontier deal was found by Cheapflights users on 7/27. 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 9/193:32 amBQN - ORD
1 stop12h 45mFrontier
Fri 10/38:49 pmORD - BQN
1 stop13h 07mFrontier
Deal found 7/27$258
This Cheapflightsfares deal was found by Cheapflights users on 7/27. 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 8/145:45 pmPUJ - ORD
Nonstop5h 08mFrontier
Mon 8/186:45 amORD - PUJ
Nonstop4h 40mFrontier
Deal found 7/27$275
This eDestinos deal was found by Cheapflights users on 7/26. 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.
Sat 9/63:19 pmPUJ - ORD
1 stop8h 29mSpirit Airlines
Wed 9/105:05 amORD - PUJ
1 stop8h 09mSpirit Airlines
Deal found 7/26$281
This Priceline deal was found by Cheapflights users on 7/26. 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 9/912:10 pmMBJ - ORD
1 stop10h 38mSpirit Airlines
Tue 9/165:05 amORD - MBJ
1 stop6h 00mSpirit Airlines
Deal found 7/26$287
This SmartFares deal was found by Cheapflights users on 7/26. 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.
Thu 8/145:42 pmSJU - MSP
2 stops15h 35mSpirit Airlines
Sat 8/239:22 amMSP - SJU
2 stops27h 55mSpirit Airlines
Deal found 7/26$288
This United Airlines deal was found by Cheapflights users on 7/27. 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.
Fri 10/173:56 pmSJU - MKE
1 stop7h 35mUnited Airlines
Mon 10/206:00 amMKE - SJU
1 stop7h 44mUnited Airlines
Deal found 7/27$294

Cheapflights Fare Finder

 
Customize your flight search to find flights from Caribbean Islands 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 July 28, 2025.
Use the filters below to find and compare flights from Caribbean Islands to Wisconsin that are best for you.

Fly from

Caribbean Islands

Fly to

Wisconsin

Route

Depart

Return

Price

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Wed 9/10

4:43 pm-10:04 am

2 stops18h 21m

Milwaukee-Mitchell

Sun 9/14

6:23 pm-12:47 pm

2 stops17h 24m

$215

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Fri 8/8

6:00 am-10:16 am

Nonstop5h 16m

Chicago O'Hare Intl

Sat 8/16

6:56 am-11:57 pm

1 stop16h 01m

$231

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Sat 8/16

4:54 pm-4:38 pm

1 stop24h 44m

Chicago O'Hare Intl

Sat 8/23

12:55 pm-6:40 pm

Nonstop4h 45m

$232

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Thu 12/4

2:26 pm-8:07 pm

1 stop7h 41m

Milwaukee-Mitchell

Wed 12/10

7:00 am-5:10 pm

1 stop8h 10m

$245

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 8/28

8:13 pm-6:41 pm

1 stop23h 28m

Chicago O'Hare Intl

Sun 8/31

5:10 am-2:26 pm

1 stop8h 16m

$252

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Wed 9/3

1:59 am-11:58 am

1 stop10h 59m

Milwaukee-Mitchell

Thu 9/18

12:53 pm-12:44 am

1 stop10h 51m

$255

AguadillaChicago

BQN - ORD

BQNORD

Aguadilla Borinquen

Fri 9/19

3:32 am-3:17 pm

1 stop12h 45m

Chicago O'Hare Intl

Fri 10/3

8:49 pm-10:56 am

1 stop13h 07m

$258

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Thu 8/14

5:45 pm-9:53 pm

Nonstop5h 08m

Chicago O'Hare Intl

Mon 8/18

6:45 am-12:25 pm

Nonstop4h 40m

$275

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Sat 9/6

3:19 pm-10:48 pm

1 stop8h 29m

Chicago O'Hare Intl

Wed 9/10

5:05 am-2:14 pm

1 stop8h 09m

$281

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Tue 9/9

12:10 pm-10:48 pm

1 stop10h 38m

Chicago O'Hare Intl

Tue 9/16

5:05 am-11:05 am

1 stop6h 00m

$287

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/26

Showing 1-10 of 60 results
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Best time to book a flight from Caribbean Islands to Wisconsin

Have a flexible travel schedule? Discover the best time to fly to Wisconsin from Caribbean Islands 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 Islands to Wisconsin

What is the cheapest month to book a flight from Caribbean Islands to Wisconsin?

Currently, February is the cheapest month in which you can book a flight from Caribbean Islands to Wisconsin (average of $280). Flying from Caribbean Islands 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 EPX to WI?

Find hourly flight availability from Caribbean Islands 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 July 28, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Caribbean Islands to Wisconsin as you normally would.

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 July 28, 2025.
Read through reviews of airlines operating flights from Caribbean Islands to Wisconsin, such as Southwest, Delta, and Copa Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,238 reviews

Food

7.0

Overall

8.0

Crew

8.6

Entertainment

7.5

Comfort

8.0

Boarding

8.1

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
4,238 reviews
Southwest
8.0
Very good
4,238 reviews

Food

7.0

Overall

8.0

Crew

8.6

Entertainment

7.5

Comfort

8.0

Boarding

8.1

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
7,975 reviews
Southwest
8.0
Very good
4,238 reviews

Food

7.0

Overall

8.0

Crew

8.6

Entertainment

7.5

Comfort

8.0

Boarding

8.1

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
4,238 reviews

Food

7.0

Overall

8.0

Crew

8.6

Entertainment

7.5

Comfort

8.0

Boarding

8.1

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
8,892 reviews
Southwest
8.0
Very good
4,238 reviews

Food

7.0

Overall

8.0

Crew

8.6

Entertainment

7.5

Comfort

8.0

Boarding

8.1

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
4,238 reviews

Food

7.0

Overall

8.0

Crew

8.6

Entertainment

7.5

Comfort

8.0

Boarding

8.1

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 Islands 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 Islands to Wisconsin one-way?

    One-way options have recently been found by users for as low as $108 on Delta. Other airlines that offer cheap prices include Frontier from $113 and Spirit Airlines from $115 one-way.

  • Can I find deals for flights from Caribbean Islands to Wisconsin that include hotel bookings?

    Yes. In addition to deals on Caribbean Islands to Wisconsin flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Caribbean Islands to Wisconsin?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Caribbean Islands to Wisconsin.

  • Can I find deals for business class flights from Caribbean Islands to Wisconsin?

    Yes. Cheapflights offers flight deals from Caribbean Islands 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 Islands to Wisconsin?

    Currently, February is the cheapest month in which you can book a flight from Caribbean Islands to Wisconsin (average of $280). Flying from Caribbean Islands 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 Islands 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 Islands to Wisconsin

Discover the top 4 airlines that operate flights from Caribbean Islands 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 July 28, 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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