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Caribbean

$96+ Cheap flights from Wisconsin to Caribbean

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.
MKE — SJU
Aug 6 — Aug 131
Wed 8/6
Wed 8/13
1 adult, Economy
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Cheap flight deals from Wisconsin to Caribbean

Keep the following information in mind while searching for Wisconsin to Caribbean flight deals. Data was last updated August 1, 2025.

Round-trip from

$199
(FlightHub)

One-way from

$98
(FlightHub)

Popular in

June

Cheapest in

September

Average price

$391
From Wisconsin to Caribbean
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One-way flight from Wisconsin to Caribbean
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Highest demand for flights based on searches. 10% potential increase in price ($50 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($12 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Find flight deals from Wisconsin to Caribbean

Cheapest flights from Wisconsin to Caribbean
Explore the most affordable flight options available from Wisconsin to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 1, 2025.

This FlightHub deal was found by Cheapflights users on 8/1. 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.
Sat 8/2311:36 amORD - STT
2 stops25h 12mSpirit Airlines
Sat 8/302:43 pmSTT - ORD
2 stops10h 16mSpirit Airlines
Deal found 8/1$199
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.
Tue 9/163:00 pmMKE - SJU
1 stop6h 45mSouthwest
Tue 9/233:05 pmSJU - MKE
1 stop7h 45mSouthwest
Deal found 7/31$215
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/216:23 pmMKE - SJU
2 stops17h 24mAmerican Airlines
Sat 9/274:45 pmSJU - MKE
2 stops18h 19mAmerican Airlines
Deal found 7/30$220
This Booking.com 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/106:23 pmORD - SJU
Nonstop4h 43mSpirit Airlines
Thu 8/147:40 pmSJU - ORD
Nonstop5h 03mSpirit Airlines
Deal found 7/30$224
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/1312:13 pmMKE - SJU
1 stop8h 47mDelta
Sat 9/205:41 pmSJU - MKE
1 stop7h 07mDelta
Deal found 7/30$225
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/175:00 amMKE - SJU
1 stop8h 44mUnited Airlines
Tue 9/231:05 amSJU - MKE
2 stops10h 08mUnited Airlines
Deal found 7/30$230
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/166:56 amORD - SJU
1 stop16h 01mMultiple Airlines
Sat 8/236:55 pmSJU - ORD
1 stop19h 10mMultiple Airlines
Deal found 7/31$232
This Frontier deal was found by Cheapflights users on 8/1. 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.
Sat 8/307:46 pmORD - SJU
1 stop12h 13mFrontier
Fri 9/53:39 amSJU - ORD
1 stop12h 38mFrontier
Deal found 8/1$238
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/165:15 amMSP - SJU
1 stop7h 38mSpirit Airlines
Thu 10/232:48 pmSJU - MSP
1 stop8h 28mSpirit Airlines
Deal found 7/29$275
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.
Sat 8/306:12 amMSP - SJU
2 stops16h 45mMultiple Airlines
Fri 9/51:59 amSJU - MSP
3 stops31h 27mMultiple Airlines
Deal found 7/30$276
This Booking.com 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/156:00 amMKE - SJU
1 stop16h 57mSpirit Airlines
Thu 8/214:05 pmSJU - MKE
1 stop8h 01mSpirit Airlines
Deal found 7/30$290
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/19:00 amMSP - SJU
Nonstop5h 14mSun Country Air
Sat 11/155:15 pmSJU - MSP
Nonstop5h 54mSun Country Air
Deal found 7/30$291

Cheapflights Fare Finder

 
Customize your flight search to find flights from Wisconsin to Caribbean 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 August 1, 2025.
Use the filters below to find and compare flights from Wisconsin to Caribbean that are best for you.

Fly from

Wisconsin

Fly to

Caribbean

Route

Depart

Return

Price

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Sat 8/23

11:36 am-1:48 pm

2 stops25h 12m

Saint Thomas Island Cyril E King

Sat 8/30

2:43 pm-11:59 pm

2 stops10h 16m

$199

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Tue 9/16

3:00 pm-10:45 pm

1 stop6h 45m

San Juan Luis Munoz Marin Intl

Tue 9/23

3:05 pm-9:50 pm

1 stop7h 45m

$215

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Sun 9/21

6:23 pm-12:47 pm

2 stops17h 24m

San Juan Luis Munoz Marin Intl

Sat 9/27

4:45 pm-10:04 am

2 stops18h 19m

$220

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sun 8/10

6:23 pm-12:06 am

Nonstop4h 43m

San Juan Luis Munoz Marin Intl

Thu 8/14

7:40 pm-11:43 pm

Nonstop5h 03m

$224

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Wed 1/21

7:00 am-4:51 pm

1 stop7h 51m

San Juan Luis Munoz Marin Intl

Thu 1/29

2:12 pm-8:12 pm

1 stop8h 00m

$225

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Wed 9/17

5:00 am-2:44 pm

1 stop8h 44m

San Juan Luis Munoz Marin Intl

Tue 9/23

1:05 am-10:13 am

2 stops10h 08m

$230

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 8/16

6:56 am-11:57 pm

1 stop16h 01m

San Juan Luis Munoz Marin Intl

Sat 8/23

6:55 pm-1:05 pm

1 stop19h 10m

$232

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 8/30

7:46 pm-8:59 am

1 stop12h 13m

San Juan Luis Munoz Marin Intl

Fri 9/5

3:39 am-3:17 pm

1 stop12h 38m

$238

MinneapolisSan Juan

MSP - SJU

MSPSJU

Minneapolis St Paul

Thu 10/16

5:15 am-1:53 pm

1 stop7h 38m

San Juan Luis Munoz Marin Intl

Thu 10/23

2:48 pm-10:16 pm

1 stop8h 28m

$275

MinneapolisSan Juan

MSP - SJU

MSPSJU

Minneapolis St Paul

Sat 8/30

6:12 am-11:57 pm

2 stops16h 45m

San Juan Luis Munoz Marin Intl

Fri 9/5

1:59 am-8:26 am

3 stops31h 27m

$276

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/1

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

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

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

Currently, September is the cheapest month in which you can book a flight from Wisconsin to Caribbean (average of $254). Flying from Wisconsin to Caribbean in June is currently the most expensive (average of $339). 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 WI to CB?

Find hourly flight availability from Wisconsin to Caribbean. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 1, 2025.

When flying from Wisconsin to Caribbean, 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 Caribbean

Get insights into the airlines that provide service to Caribbean. 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 Caribbean. Reviews last updated August 1, 2025.
See what other customers who have flown with Delta, Southwest, and Copa Airlines from Wisconsin to Caribbean have to say. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,983 reviews

Overall

8.0

Comfort

7.9

Boarding

8.2

Crew

8.5

Food

7.3

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,983 reviews
Delta
8.0
Very good
7,983 reviews

Overall

8.0

Comfort

7.9

Boarding

8.2

Crew

8.5

Food

7.3

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Southwest
8.0
Very good
4,246 reviews
Delta
8.0
Very good
7,983 reviews

Overall

8.0

Comfort

7.9

Boarding

8.2

Crew

8.5

Food

7.3

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Copa Airlines
7.5
Good
1,493 reviews
Delta
8.0
Very good
7,983 reviews

Overall

8.0

Comfort

7.9

Boarding

8.2

Crew

8.5

Food

7.3

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
United Airlines
7.4
Good
8,904 reviews
Delta
8.0
Very good
7,983 reviews

Overall

8.0

Comfort

7.9

Boarding

8.2

Crew

8.5

Food

7.3

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,983 reviews

Overall

8.0

Comfort

7.9

Boarding

8.2

Crew

8.5

Food

7.3

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

Related info for your journey

Find useful and relevant information for your journey from Wisconsin to Caribbean. 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 Wisconsin to Caribbean one-way?

    For one-way options, check prices for Spirit Airlines. According to our data, you can fly for as low as $98. Users have also found prices from $107 and $108 on American Airlines and Delta, respectively.

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

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

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

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

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

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

    Currently, September is the cheapest month in which you can book a flight from Wisconsin to Caribbean (average of $254). Flying from Wisconsin to Caribbean in June is currently the most expensive (average of $339). 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 Wisconsin to Caribbean

See prices for flight routes from nearby airports that may be better suited for you.
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Top 7 airlines flying from Wisconsin to Caribbean

Discover the top 7 airlines that operate flights from Wisconsin to Caribbean. 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 August 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$129Average$230FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$208Average$394FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$215Average$675FlexibilityNo cancel feeOn-time69%
DeltaCheapest$225Average$663FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$269Average$679FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$325Average$744FlexibilityNo cancel feeOn-time63%
Sun Country AirCheapest$519Average$649FlexibilityNo cancel feeOn-time83%

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