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$88+ 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 2/24. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SJU
Feb 26 — Mar 51
Thu 2/26
Thu 3/5
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 January 27, 2026.

This Rumbo deal was found by Cheapflights users on 1/26. 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 Rumbo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/27:44 am
ORD
-
SJU
1 stop9h 39m
JetBlue
Wed 2/119:25 am
SJU
-
ORD
1 stop12h 06m
JetBlue
Deal found 1/26$185
This Expedia deal was found by Cheapflights users on 1/26. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/218:31 am
ORD
-
SJU
1 stop8h 59m
Multiple Airlines
Mon 4/274:11 pm
SJU
-
ORD
1 stop8h 05m
Multiple Airlines
Deal found 1/26$186
This Cheapflightsfares deal was found by Cheapflights users on 1/27. 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.
Mon 2/912:17 pm
ORD
-
SJU
Nonstop4h 32m
Spirit Airlines
Sat 2/1412:32 pm
SJU
-
ORD
Nonstop5h 16m
Spirit Airlines
Deal found 1/27$187
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/812:17 pm
ORD
-
SJU
Nonstop4h 32m
Spirit Airlines
Fri 2/1312:32 pm
SJU
-
ORD
Nonstop5h 16m
Spirit Airlines
Deal found 1/27$188
This Booking.com deal was found by Cheapflights users on 1/27. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/88:43 pm
ORD
-
SJU
1 stop16h 52m
Spirit Airlines
Sat 2/144:36 pm
SJU
-
ORD
1 stop9h 11m
Spirit Airlines
Deal found 1/27$189
This Kiwi.com deal was found by Cheapflights users on 1/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/710:55 am
ORD
-
SJU
1 stop12h 03m
Spirit Airlines
Sun 4/121:29 am
SJU
-
ORD
Nonstop5h 16m
Spirit Airlines
Deal found 1/26$190
This JetBlue deal was found by Cheapflights users on 1/25. 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.
Wed 2/1810:00 am
ORD
-
SJU
1 stop10h 53m
JetBlue
Tue 2/245:10 am
SJU
-
ORD
1 stop8h 49m
JetBlue
Deal found 1/25$191
This JetBlue deal was found by Cheapflights users on 1/27. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/88:15 am
ORD
-
SJU
1 stop9h 25m
JetBlue
Thu 4/911:00 am
SJU
-
ORD
1 stop11h 33m
JetBlue
Deal found 1/27$192
This Priceline deal was found by Cheapflights users on 1/26. 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.
Sat 4/1110:55 am
ORD
-
SJU
1 stop12h 03m
Spirit Airlines
Mon 4/131:29 am
SJU
-
ORD
Nonstop5h 16m
Spirit Airlines
Deal found 1/26$193
This Kiwi.com deal was found by Cheapflights users on 1/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/312:44 pm
ORD
-
SJU
1 stop8h 49m
Multiple Airlines
Thu 2/57:10 am
SJU
-
ORD
1 stop13h 19m
Multiple Airlines
Deal found 1/26$194
This CheapOair deal was found by Cheapflights users on 1/27. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/153:15 pm
ORD
-
SJU
1 stop9h 52m
Multiple Airlines
Tue 5/1912:22 pm
SJU
-
ORD
Nonstop5h 15m
Multiple Airlines
Deal found 1/27$195
This CheapOair deal was found by Cheapflights users on 1/27. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/114:21 pm
ORD
-
SJU
1 stop14h 35m
Multiple Airlines
Thu 4/1612:22 pm
SJU
-
ORD
Nonstop5h 15m
Multiple Airlines
Deal found 1/27$196

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 January 27, 2026.

Round-trip from

$185
(Orbitz)

One-way from

$88
(Travelocity)

Popular in

December

Cheapest in

September

Average price

$401

Good round-trip deal

$676 or less
From Wisconsin to Caribbean
Search Deals
One-way flight from Wisconsin to Caribbean
Search Deals
Highest demand for flights based on searches. 15% potential increase in price ($82 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($20 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
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 January 27, 2026.
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 2/16

10:00 am-10:53 pm

1 stop10h 53m

San Juan Luis Munoz Marin Intl

Fri 2/27

1:44 pm-10:59 pm

1 stop11h 15m

$191

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Thu 4/9

10:00 am-10:01 pm

1 stop11h 01m

San Juan Luis Munoz Marin Intl

Wed 4/15

11:59 pm-7:41 am

1 stop8h 42m

$192

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mon 3/9

12:41 pm-11:29 pm

1 stop9h 48m

San Juan Luis Munoz Marin Intl

Mon 3/16

3:26 am-11:25 am

1 stop8h 59m

$192

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 5/30

3:15 pm-12:59 am

1 stop8h 44m

San Juan Luis Munoz Marin Intl

Wed 6/3

12:30 pm-7:26 pm

1 stop7h 56m

$203

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Fri 6/5

3:15 pm-1:59 am

1 stop9h 44m

San Juan Luis Munoz Marin Intl

Tue 6/9

12:30 pm-7:26 pm

1 stop7h 56m

$203

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 2/21

6:04 am-4:56 pm

1 stop8h 52m

San Juan Luis Munoz Marin Intl

Wed 2/25

1:44 pm-10:59 pm

1 stop11h 15m

$203

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 3/7

12:59 pm-11:44 pm

1 stop8h 45m

San Juan Luis Munoz Marin Intl

Wed 3/11

3:26 am-11:25 am

1 stop8h 59m

$203

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Wed 2/18

10:00 am-10:53 pm

1 stop10h 53m

San Juan Luis Munoz Marin Intl

Fri 2/27

1:44 pm-10:59 pm

1 stop11h 15m

$203

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Wed 2/25

12:59 pm-12:29 am

1 stop9h 30m

San Juan Luis Munoz Marin Intl

Sun 3/1

5:05 am-12:04 pm

1 stop8h 59m

$212

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Wed 5/20

3:15 pm-2:07 am

1 stop9h 52m

San Juan Luis Munoz Marin Intl

Tue 5/26

3:30 am-2:20 pm

1 stop11h 50m

$217

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/25

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 $378). 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 January 27, 2026.

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.

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 JetBlue, Spirit Airlines, and Frontier fly from Wisconsin to Caribbean in about 8h 20m. The time it takes to get you to your destination can typically vary by up to 2h 33m. The distance between Wisconsin and Caribbean is about 2302 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 $85. Users have also found prices from $108 and $108 on United 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, 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 $378). 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.
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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 January 27, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$85Average$291FlexibilityNo cancel feeOn-time62%
DeltaCheapest$118Average$679FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$158Average$630FlexibilityNo cancel feeOn-time69%
Spirit AirlinesCheapest$208Average$402FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$215Average$666FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$315Average$736FlexibilityNo cancel feeOn-time63%
Sun Country AirCheapest$497Average$652FlexibilityNo cancel feeOn-time83%

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