HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Caribbean

$84+ 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 1/20. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SJU
Nov 26 — Dec 31
Tue 11/26
Tue 12/3
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Wisconsin to Caribbean with Cheapflights

1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”
2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.
3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Wisconsin to Caribbean

Discover tips and strategies to find the most affordable flight options for your journey from Wisconsin (USWI) to Caribbean (0CB). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated November 21, 2024.

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 November 21, 2024.

This Kiwi.com deal was found by Cheapflights users on 11/20. 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.
Sat 12/71:00 pmORD - SJU
Nonstop4h 36mSpirit Airlines
Thu 12/122:17 pmSJU - ORD
Nonstop5h 30mSpirit Airlines
Deal found 11/20$170
This FlightHub deal was found by Cheapflights users on 11/21. 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.
Sun 12/89:35 amORD - SJU
1 stop26h 19mFrontier
Thu 12/125:05 pmSJU - ORD
1 stop18h 49mFrontier
Deal found 11/21$175
This Justfly.com deal was found by Cheapflights users on 11/20. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/89:35 amORD - SJU
1 stop26h 19mMultiple Airlines
Thu 12/122:17 pmSJU - ORD
Nonstop5h 30mMultiple Airlines
Deal found 11/20$177
This FlightHub deal was found by Cheapflights users on 11/21. 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.
Sun 12/151:02 pmMSP - SJU
1 stop10h 40mMultiple Airlines
Sat 12/215:25 pmSJU - MSP
1 stop19h 02mMultiple Airlines
Deal found 11/21$209
This United Airlines deal was found by Cheapflights users on 11/21. 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.
Mon 12/92:20 pmORD - SJU
Nonstop4h 35mUnited Airlines
Fri 12/132:05 amSJU - ORD
1 stop10h 48mUnited Airlines
Deal found 11/21$226
This CheapOair deal was found by Cheapflights users on 11/21. 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.
Fri 12/131:02 pmMSP - SJU
1 stop10h 40mSpirit Airlines
Wed 12/184:30 amSJU - MSP
2 stops13h 06mSpirit Airlines
Deal found 11/21$227
This Frontier deal was found by Cheapflights users on 11/21. 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.
Tue 12/1711:27 amMSP - SJU
1 stop13h 22mFrontier
Fri 12/203:54 amSJU - MSP
1 stop8h 33mFrontier
Deal found 11/21$228
This Mytrip deal was found by Cheapflights users on 11/21. 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.
Sat 12/75:23 pmMSP - MBJ
2 stops19h 10mMultiple Airlines
Sat 12/143:35 pmMBJ - MSP
Nonstop4h 59mMultiple Airlines
Deal found 11/21$267
This FlightHub deal was found by Cheapflights users on 11/21. 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 12/46:00 amORD - PUJ
Nonstop4h 29mFrontier
Wed 12/115:00 pmPUJ - ORD
Nonstop5h 31mFrontier
Deal found 11/21$269
This Kiwi.com deal was found by Cheapflights users on 11/20. 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.
Fri 12/136:07 pmORD - PUJ
1 stop15h 24mMultiple Airlines
Wed 12/182:35 pmPUJ - ORD
1 stop7h 38mMultiple Airlines
Deal found 11/20$281
This FlightHub deal was found by Cheapflights users on 11/20. 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.
Fri 12/137:45 pmORD - STT
1 stop15h 38mSpirit Airlines
Fri 1/1711:46 amSTT - ORD
1 stop13h 16mSpirit Airlines
Deal found 11/20$324
This Mytrip deal was found by Cheapflights users on 11/20. 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.
Mon 12/239:25 pmORD - STT
3 stops35h 14mMultiple Airlines
Tue 12/3111:44 amSTT - ORD
1 stop10h 07mMultiple Airlines
Deal found 11/20$337

Find flights from Wisconsin to Caribbean within your budget

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 2,612,795 searches. Data last updated November 21, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 12/7

1:00 pm-7:36 pm

Nonstop4h 36m

San Juan Luis Munoz Marin Intl

Thu 12/12

2:17 pm-5:47 pm

Nonstop5h 30m

$170

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sun 2/2

4:18 pm-10:37 am

1 stop16h 19m

San Juan Luis Munoz Marin Intl

Thu 2/6

9:49 pm-9:52 am

1 stop14h 03m

$173

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Wed 1/8

8:14 pm-11:18 am

1 stop13h 04m

San Juan Luis Munoz Marin Intl

Wed 1/15

4:49 pm-1:50 pm

1 stop23h 01m

$174

MinneapolisSan Juan

MSP - SJU

MSPSJU

Minneapolis St Paul

Thu 2/6

10:14 am-2:19 am

1 stop14h 05m

San Juan Luis Munoz Marin Intl

Sun 2/9

9:49 pm-9:24 am

1 stop13h 35m

$188

MinneapolisSan Juan

MSP - SJU

MSPSJU

Minneapolis St Paul

Sun 12/15

1:02 pm-1:42 am

1 stop10h 40m

San Juan Luis Munoz Marin Intl

Sat 12/21

5:25 pm-10:27 am

1 stop19h 02m

$209

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mon 12/9

2:20 pm-8:55 pm

Nonstop4h 35m

San Juan Luis Munoz Marin Intl

Fri 12/13

2:05 am-9:43 am

1 stop9h 38m

$226

MinneapolisSan Juan

MSP - SJU

MSPSJU

Minneapolis St Paul

Fri 12/13

1:02 pm-1:42 am

1 stop10h 40m

San Juan Luis Munoz Marin Intl

Wed 12/18

4:30 am-3:36 pm

2 stops13h 06m

$227

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Wed 12/4

6:00 am-12:29 pm

Nonstop4h 29m

Punta Cana

Wed 12/11

5:00 pm-8:31 pm

Nonstop5h 31m

$265

MinneapolisMontego Bay

MSP - MBJ

MSPMBJ

Minneapolis St Paul

Sat 12/7

5:23 pm-1:33 pm

2 stops19h 10m

Montego Bay Sangster Intl

Sat 12/14

3:35 pm-7:34 pm

Nonstop4h 59m

$267

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Sat 1/25

5:10 am-3:49 pm

1 stop8h 39m

Punta Cana

Tue 1/28

6:54 pm-10:11 pm

Nonstop5h 17m

$268

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/21

Showing 1-10 of 60 results
1
2
3
...
6

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.

Travel insights for flights from Wisconsin to Caribbean

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

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 March is currently the most expensive (average of $335). 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 November 21, 2024.

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 November 21, 2024.
Southwest
8.1
Very good
5,005 reviews

Food

7.2

Entertainment

7.7

Comfort

8.1

Boarding

8.2

Crew

8.7

Overall

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Southwest
8.1
Very good
5,005 reviews
Southwest
8.1
Very good
5,005 reviews

Food

7.2

Entertainment

7.7

Comfort

8.1

Boarding

8.2

Crew

8.7

Overall

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Delta
8.0
Very good
8,755 reviews
Southwest
8.1
Very good
5,005 reviews

Food

7.2

Entertainment

7.7

Comfort

8.1

Boarding

8.2

Crew

8.7

Overall

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Alaska Airlines
8.0
Very good
9,464 reviews
Southwest
8.1
Very good
5,005 reviews

Food

7.2

Entertainment

7.7

Comfort

8.1

Boarding

8.2

Crew

8.7

Overall

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Copa Airlines
7.8
Good
1,779 reviews
Southwest
8.1
Very good
5,005 reviews

Food

7.2

Entertainment

7.7

Comfort

8.1

Boarding

8.2

Crew

8.7

Overall

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

United Airlines
7.4
Good
9,172 reviews
Southwest
8.1
Very good
5,005 reviews

Food

7.2

Entertainment

7.7

Comfort

8.1

Boarding

8.2

Crew

8.7

Overall

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

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 Frontier. According to our data, you can fly for as low as $84. Users have also found prices from $91 and $105 on Spirit Airlines and United Airlines, 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 March is currently the most expensive (average of $335). 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 Wisconsin to Caribbean

See prices for flight routes from nearby airports that may be better suited for you.
LaGuardia to Fort Lauderdale flights
Newark to Fort Lauderdale flights
John F Kennedy Intl to Miami flights
Newark to Miami flights
LaGuardia to Miami flights
Newark to Cancún flights
John F Kennedy Intl to Cancún flights
Dallas/Fort Worth to LaGuardia flights
Los Angeles to John F Kennedy Intl flights
LaGuardia to Dallas/Fort Worth flights
John F Kennedy Intl to Orlando flights
John F Kennedy Intl to Los Angeles flights
Newark to Los Angeles flights
Los Angeles to Newark flights
O'Hare Intl to Cancún flights
Dallas/Fort Worth to John F Kennedy Intl flights
Newark to Orlando flights
John F Kennedy Intl to Heathrow flights
Newark to Heathrow flights
John F Kennedy Intl to Las Vegas flights
John F Kennedy Intl to Luis Munoz Marin Intl flights
Dallas/Fort Worth to Newark flights
LaGuardia to Orlando flights
Atlanta to John F Kennedy Intl flights
Miami to John F Kennedy Intl flights
John F Kennedy Intl to Dallas/Fort Worth flights
San Francisco to John F Kennedy Intl flights
Newark to Dallas/Fort Worth flights
John F Kennedy Intl to Fort Lauderdale flights
John F Kennedy Intl to San Francisco flights
Miami to LaGuardia flights
John F Kennedy Intl to Atlanta flights
Fort Lauderdale to LaGuardia flights
Newark to Luis Munoz Marin Intl flights
Fort Lauderdale to Newark flights
Los Angeles to Honolulu flights
Los Angeles to Dallas/Fort Worth flights
Dallas/Fort Worth to Las Vegas flights
Los Angeles to Haneda flights
Dallas/Fort Worth to Cancún flights
Dallas/Fort Worth to Orlando flights
Los Angeles to LaGuardia flights
Fort Lauderdale to John F Kennedy Intl flights
Los Angeles to Seattle flights
John F Kennedy Intl to Gatwick flights
John F Kennedy Intl to Charles de Gaulle flights
Dallas/Fort Worth to Los Angeles flights
Boston to Orlando flights
Orlando to John F Kennedy Intl flights
LaGuardia to Cancún flights

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 2,612,795 searches. Data last updated November 21, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$157Average$354FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$168Average$420FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$258Average$637FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$274Average$647FlexibilityNo cancel feeOn-time69%
DeltaCheapest$284Average$655FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$325Average$707FlexibilityNo cancel feeOn-time63%
JetBlueCheapest$360Average$591FlexibilityNo cancel feeOn-time62%
Sun Country AirCheapest$398Average$677FlexibilityNo cancel feeOn-time83%
100% Free
Cheapflights is completely free to use, so you can start saving the moment you arrive.
Book with Flexibility
Our users can plan ahead with confidence and find flights with no change fees
Travel Smart
Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.
View all available airlines