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$80+ 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 1/6. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SJU
Jan 15 — Jan 221
Thu 1/15
Thu 1/22
1 adult, Economy
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Cheap 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 December 16, 2025.

This Frontier deal was found by Cheapflights users on 12/14. 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 12/301:27 pmORD - SJU
1 stop15h 07mFrontier
Thu 1/154:35 pmSJU - ORD
1 stop8h 09mFrontier
Deal found 12/14$201
This JetBlue deal was found by Cheapflights users on 12/14. 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.
Sat 12/276:45 amORD - SJU
1 stop7h 39mJetBlue
Tue 12/302:21 pmSJU - ORD
1 stop9h 43mJetBlue
Deal found 12/14$202
This Kiwi.com deal was found by Cheapflights users on 12/14. 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.
Wed 12/316:05 pmORD - SJU
1 stop12h 34mMultiple Airlines
Thu 1/154:35 pmSJU - ORD
1 stop8h 09mMultiple Airlines
Deal found 12/14$203
This Frontier deal was found by Cheapflights users on 12/15. 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.
Wed 12/312:15 pmORD - SJU
1 stop8h 14mFrontier
Thu 1/1511:55 amSJU - ORD
1 stop8h 30mFrontier
Deal found 12/15$205
This Priceline deal was found by Cheapflights users on 12/15. 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 12/1611:25 amORD - SJU
1 stop10h 29mMultiple Airlines
Tue 12/238:08 pmSJU - ORD
Nonstop5h 17mMultiple Airlines
Deal found 12/15$230
This Frontier deal was found by Cheapflights users on 12/14. 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 12/301:27 pmORD - SJU
1 stop15h 07mFrontier
Mon 1/124:39 pmSJU - ORD
1 stop8h 00mFrontier
Deal found 12/14$233
This deal was found by Cheapflights users on 12/14. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/3112:39 pmORD - SJU
1 stop9h 15mFrontier
Tue 1/139:00 amSJU - ORD
1 stop9h 52mFrontier
Deal found 12/14$235
This American Airlines deal was found by Cheapflights users on 12/15. 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 12/3110:25 pmORD - SJU
Nonstop4h 35mAmerican Airlines
Thu 1/156:00 amSJU - ORD
Nonstop5h 35mAmerican Airlines
Deal found 12/15$236
This Frontier deal was found by Cheapflights users on 12/14. 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.
Wed 12/312:15 pmORD - SJU
1 stop8h 14mFrontier
Sun 1/112:29 amSJU - ORD
1 stop13h 53mFrontier
Deal found 12/14$237
This Frontier deal was found by Cheapflights users on 12/14. 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.
Mon 12/292:15 pmORD - SJU
1 stop8h 14mFrontier
Tue 1/139:00 amSJU - ORD
1 stop9h 52mFrontier
Deal found 12/14$240
This Expedia deal was found by Cheapflights users on 12/15. 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.
Mon 12/227:10 amORD - PUJ
Nonstop4h 37mMultiple Airlines
Sat 12/277:17 amPUJ - ORD
Nonstop5h 10mMultiple Airlines
Deal found 12/15$303
This Expedia deal was found by Cheapflights users on 12/14. 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.
Tue 12/167:10 amORD - PUJ
Nonstop4h 37mMultiple Airlines
Tue 12/237:30 pmPUJ - ORD
Nonstop5h 10mMultiple Airlines
Deal found 12/14$314

Find flight deals from Wisconsin to Caribbean

Keep the following information in mind while searching for Wisconsin to Caribbean flight deals. Data was last updated December 16, 2025.

Round-trip from

$194
(Kiwi.com)

One-way from

$80
(Super.com)

Popular in

June

Cheapest in

September

Average price

$532

Good round-trip deal

$716 or less
From Wisconsin to Caribbean
Search Deals
One-way flight from Wisconsin to Caribbean
Search Deals
Highest demand for flights based on searches. 9% potential increase in price ($48 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($12 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals
Price to beat on a round-trip flight from Wisconsin to Caribbean.
Search Deals

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 December 16, 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 2/2

4:19 pm-12:45 pm

2 stops18h 26m

San Juan Luis Munoz Marin Intl

Thu 2/5

4:22 pm-10:46 pm

1 stop8h 24m

$198

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 1/20

7:45 am-6:07 pm

1 stop8h 22m

San Juan Luis Munoz Marin Intl

Sat 1/24

10:25 am-7:36 pm

1 stop11h 11m

$205

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 1/6

10:55 am-12:14 am

1 stop11h 19m

San Juan Luis Munoz Marin Intl

Tue 1/13

11:06 am-7:36 pm

1 stop10h 30m

$205

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sun 2/1

7:45 am-6:05 pm

1 stop8h 20m

San Juan Luis Munoz Marin Intl

Mon 2/16

5:22 pm-11:10 pm

1 stop7h 48m

$205

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sun 3/8

12:41 pm-10:44 pm

1 stop9h 03m

San Juan Luis Munoz Marin Intl

Fri 3/13

1:30 am-10:05 am

1 stop9h 35m

$228

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Thu 3/5

12:41 pm-11:44 pm

1 stop9h 03m

San Juan Luis Munoz Marin Intl

Sat 3/7

4:15 am-11:49 am

1 stop8h 34m

$231

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Sat 5/2

6:45 am-3:07 pm

1 stop7h 22m

San Juan Luis Munoz Marin Intl

Thu 5/7

6:15 am-3:05 pm

1 stop9h 50m

$235

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Wed 3/4

1:35 pm-11:58 pm

1 stop8h 23m

San Juan Luis Munoz Marin Intl

Wed 3/11

7:30 am-5:29 pm

1 stop10h 59m

$235

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Mon 2/23

12:20 pm-9:12 pm

1 stop6h 52m

San Juan Luis Munoz Marin Intl

Fri 2/27

2:16 pm-8:36 pm

1 stop8h 20m

$235

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Sun 2/22

5:23 am-2:32 pm

1 stop7h 09m

San Juan Luis Munoz Marin Intl

Thu 3/5

6:27 pm-11:48 pm

1 stop7h 21m

$235

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/14

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, November is the cheapest month in which you can book a flight from Wisconsin to Caribbean (average of $113). Flying from Wisconsin to Caribbean in June is currently the most expensive (average of $379). 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 December 16, 2025.

It’s typically best to fly out from Wisconsin to Caribbean at noon. Doing so could potentially save you 20% on the flight price compared to flying in the morning, which is usually more expensive.

What is the cheapest day to fly from Wisconsin to Caribbean?

Use this chart to determine the cheapest time to fly round-trip from Wisconsin to Caribbean. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Wisconsin to Caribbean flight should consider departing on Sunday afternoons when fares are most often at their lowest. Monday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

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.

  • How long is the flight from Wisconsin to Caribbean?

    Airlines like Frontier, JetBlue, and Delta fly from Wisconsin to Caribbean in about 7h 51m. The time it takes to get you to your destination can typically vary by up to 10h 35m. The distance between Wisconsin and Caribbean is about 2120 mi. This flight may include one or multiple stops.

  • 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 $43. Users have also found prices from $108 and $108 on United Airlines and Southwest, 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, November is the cheapest month in which you can book a flight from Wisconsin to Caribbean (average of $113). Flying from Wisconsin to Caribbean in June is currently the most expensive (average of $379). 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 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 December 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$129Average$256FlexibilityNo cancel feeOn-time62%
DeltaCheapest$191Average$673FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$215Average$671FlexibilityNo cancel feeOn-time69%
Spirit AirlinesCheapest$226Average$406FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$268Average$666FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$315Average$754FlexibilityNo cancel feeOn-time63%
Sun Country AirCheapest$497Average$652FlexibilityNo cancel feeOn-time83%

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