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$113+ 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 7/22. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SJU
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
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 June 12, 2025.

Round-trip from

$210
(FlightHub)

One-way from

$113
(SmartFares)

Popular in

June

Cheapest in

September

Average price

$571
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. 9% potential increase in price ($45 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 June 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 June 12, 2025.

This FlightHub deal was found by Cheapflights users on 6/10. 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.
Mon 8/187:45 amORD - SJU
1 stop7h 58mFrontier
Thu 8/213:21 pmSJU - ORD
1 stop9h 33mFrontier
Deal found 6/10$210
This Cheapflightsfares deal was found by Cheapflights users on 6/11. 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.
Tue 7/810:43 amORD - SJU
1 stop12h 22mSpirit Airlines
Tue 7/154:43 pmSJU - ORD
1 stop15h 21mSpirit Airlines
Deal found 6/11$214
This Priceline deal was found by Cheapflights users on 6/11. 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.
Sat 7/1212:20 pmORD - SJU
1 stop11h 07mMultiple Airlines
Tue 7/224:43 pmSJU - ORD
1 stop15h 21mMultiple Airlines
Deal found 6/11$220
This Delta deal was found by Cheapflights users on 6/10. 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.
Tue 9/166:00 amMKE - SJU
1 stop9h 08mDelta
Tue 9/235:19 pmSJU - MKE
1 stop7h 06mDelta
Deal found 6/10$225
This United Airlines deal was found by Cheapflights users on 6/12. 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.
Sat 11/810:53 amMKE - SJU
2 stops9h 29mUnited Airlines
Fri 11/142:05 amSJU - MKE
1 stop10h 14mUnited Airlines
Deal found 6/12$250
This Cheapflightsfares deal was found by Cheapflights users on 6/11. 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 9/252:22 pmMSP - SJU
1 stop8h 50mSpirit Airlines
Sun 9/281:10 amSJU - MSP
1 stop13h 07mSpirit Airlines
Deal found 6/11$256
This Cheapflightsfares deal was found by Cheapflights users on 6/10. 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.
Tue 7/87:49 pmORD - STT
1 stop15h 41mSpirit Airlines
Tue 7/151:25 pmSTT - ORD
1 stop10h 46mSpirit Airlines
Deal found 6/10$271
This American Airlines deal was found by Cheapflights users on 6/11. 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 9/77:04 amMKE - SJU
1 stop6h 55mAmerican Airlines
Sat 9/134:45 pmSJU - MKE
2 stops18h 47mAmerican Airlines
Deal found 6/11$275
This Mytrip deal was found by Cheapflights users on 6/10. 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.
Mon 7/77:48 amMSP - SJU
2 stops27h 09mMultiple Airlines
Wed 7/94:43 pmSJU - MSP
2 stops20h 33mMultiple Airlines
Deal found 6/10$276
This American Airlines deal was found by Cheapflights users on 6/10. 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.
Tue 7/18:35 amORD - PUJ
Nonstop4h 35mAmerican Airlines
Fri 7/43:31 pmPUJ - ORD
Nonstop5h 05mAmerican Airlines
Deal found 6/10$294
This Sun Country Air deal was found by Cheapflights users on 6/9. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/69:00 amMSP - SJU
Nonstop5h 14mSun Country Air
Thu 12/115:06 pmSJU - MSP
Nonstop5h 54mSun Country Air
Deal found 6/9$296
This JetBlue deal was found by Cheapflights users on 6/10. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/44:05 pmORD - SJU
1 stop7h 38mJetBlue
Tue 11/117:30 amSJU - ORD
1 stop9h 38mJetBlue
Deal found 6/10$297

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 June 12, 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

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mon 8/18

7:45 am-4:43 pm

1 stop7h 58m

San Juan Luis Munoz Marin Intl

Thu 8/21

3:21 pm-11:54 pm

1 stop9h 33m

$210

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 7/8

10:43 am-12:05 am

1 stop12h 22m

San Juan Luis Munoz Marin Intl

Tue 7/15

4:43 pm-7:04 am

1 stop15h 21m

$214

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 7/12

12:20 pm-12:27 am

1 stop11h 07m

San Juan Luis Munoz Marin Intl

Tue 7/22

4:43 pm-7:04 am

1 stop15h 21m

$220

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Sat 8/30

6:00 am-4:36 pm

1 stop9h 36m

San Juan Luis Munoz Marin Intl

Sat 9/6

7:30 am-1:51 pm

1 stop7h 21m

$225

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Tue 7/8

7:49 pm-12:30 pm

1 stop15h 41m

Saint Thomas Island Cyril E King

Tue 7/15

1:25 pm-11:11 pm

1 stop10h 46m

$271

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Sun 9/7

7:04 am-2:59 pm

1 stop6h 55m

San Juan Luis Munoz Marin Intl

Sat 9/13

4:45 pm-10:32 am

2 stops18h 47m

$275

MinneapolisSan Juan

MSP - SJU

MSPSJU

Minneapolis St Paul

Mon 7/7

7:48 am-11:57 am

2 stops27h 09m

San Juan Luis Munoz Marin Intl

Wed 7/9

4:43 pm-12:16 pm

2 stops20h 33m

$276

MinneapolisSan Juan

MSP - SJU

MSPSJU

Minneapolis St Paul

Mon 8/18

2:22 pm-1:11 am

2 stops9h 49m

San Juan Luis Munoz Marin Intl

Mon 8/25

5:41 pm-12:31 am

1 stop7h 50m

$286

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Tue 7/1

8:35 am-2:10 pm

Nonstop4h 35m

Punta Cana

Fri 7/4

3:31 pm-7:36 pm

Nonstop5h 05m

$294

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Fri 8/22

7:45 am-4:46 pm

1 stop8h 01m

San Juan Luis Munoz Marin Intl

Thu 8/28

5:41 pm-6:40 am

1 stop13h 59m

$298

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/11

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 June 12, 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.

Rainfall in Caribbean by month

Plan your trip to Caribbean by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Caribbean ranges from 2.2 - 6.1 inches per month. November is typically the wettest month, when rainfall can reach 6.1 in. February is typically the driest time to visit Caribbean when rainfall is around 2.2 in.

Temperature in Caribbean by month

Plan your trip to Caribbean by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Caribbean, use this chart to help with planning. For those seeking warmer temperatures, June is the ideal time of year to visit, when temperatures reach an average of 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 77.0 F).

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 June 12, 2025.
Delta
8.0
Very good
7,950 reviews

Boarding

8.2

Comfort

7.9

Food

7.3

Overall

8.0

Entertainment

7.9

Crew

8.5

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
7,950 reviews
Delta
8.0
Very good
7,950 reviews

Boarding

8.2

Comfort

7.9

Food

7.3

Overall

8.0

Entertainment

7.9

Crew

8.5

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
4,287 reviews
Delta
8.0
Very good
7,950 reviews

Boarding

8.2

Comfort

7.9

Food

7.3

Overall

8.0

Entertainment

7.9

Crew

8.5

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!
Finnair
7.6
Good
1,290 reviews
Delta
8.0
Very good
7,950 reviews

Boarding

8.2

Comfort

7.9

Food

7.3

Overall

8.0

Entertainment

7.9

Crew

8.5

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
1,451 reviews
Delta
8.0
Very good
7,950 reviews

Boarding

8.2

Comfort

7.9

Food

7.3

Overall

8.0

Entertainment

7.9

Crew

8.5

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
8,790 reviews
Delta
8.0
Very good
7,950 reviews

Boarding

8.2

Comfort

7.9

Food

7.3

Overall

8.0

Entertainment

7.9

Crew

8.5

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 $113. Users have also found prices from $113 and $115 on Southwest and Frontier, 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 8 airlines flying from Wisconsin to Caribbean

Discover the top 8 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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$129Average$239FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$195Average$474FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$225Average$680FlexibilityNo cancel feeOn-time69%
JetBlueCheapest$248Average$445FlexibilityNo cancel feeOn-time62%
DeltaCheapest$264Average$642FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$269Average$681FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$332Average$750FlexibilityNo cancel feeOn-time63%
Sun Country AirCheapest$495Average$647FlexibilityNo cancel feeOn-time83%

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