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Wisconsin

$106+ Cheap flights from Caribbean to Wisconsin

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.
SJU — MKE
Dec 3 — Dec 101
Wed 12/3
Wed 12/10
1 adult, Economy
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Find flight deals from Caribbean to Wisconsin

Cheapest flights from Caribbean to Wisconsin
Explore the most affordable flight options available from Caribbean to Wisconsin. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 3, 2025.

This Kiwi.com deal was found by Cheapflights users on 11/3. 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 12/64:31 pmSJU - ORD
1 stop7h 53mMultiple Airlines
Mon 12/85:40 amORD - SJU
Nonstop4h 41mMultiple Airlines
Deal found 11/3$176
This Mytrip deal was found by Cheapflights users on 11/3. 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.
Thu 12/48:45 pmSJU - ORD
Nonstop5h 14mMultiple Airlines
Sun 12/76:00 amORD - SJU
1 stop12h 08mMultiple Airlines
Deal found 11/3$178
This Kiwi.com deal was found by Cheapflights users on 11/2. 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 12/511:47 amSJU - ORD
1 stop8h 49mMultiple Airlines
Mon 12/83:23 pmORD - SJU
1 stop7h 26mMultiple Airlines
Deal found 11/2$187
This Mytrip deal was found by Cheapflights users on 11/2. 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.
Thu 11/133:37 pmSJU - ORD
1 stop10h 50mMultiple Airlines
Mon 11/175:05 amORD - SJU
1 stop8h 14mMultiple Airlines
Deal found 11/2$189
This Kiwi.com deal was found by Cheapflights users on 11/2. 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.
Thu 11/204:05 pmSJU - ORD
1 stop10h 03mMultiple Airlines
Tue 12/28:41 amORD - SJU
Nonstop4h 36mMultiple Airlines
Deal found 11/2$192
This Kiwi.com deal was found by Cheapflights users on 11/3. 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 12/54:10 amSJU - ORD
1 stop8h 58mSpirit Airlines
Mon 12/89:14 pmORD - SJU
1 stop24h 11mSpirit Airlines
Deal found 11/3$194
This eDestinos deal was found by Cheapflights users on 11/3. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/54:31 pmSJU - ORD
1 stop7h 53mFrontier
Mon 12/86:11 amORD - SJU
1 stop7h 00mFrontier
Deal found 11/3$196
This Kiwi.com deal was found by Cheapflights users on 11/3. 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.
Thu 12/44:31 pmSJU - ORD
1 stop7h 53mFrontier
Sun 12/73:47 pmORD - SJU
2 stops31h 02mFrontier
Deal found 11/3$201
This Kiwi.com deal was found by Cheapflights users on 11/3. 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.
Thu 12/114:31 pmSJU - ORD
1 stop7h 53mMultiple Airlines
Mon 12/155:40 amORD - SJU
Nonstop4h 41mMultiple Airlines
Deal found 11/3$206
This Orbitz deal was found by Cheapflights users on 11/2. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/225:47 amPUJ - ORD
Nonstop5h 10mArajet
Sat 11/2910:27 amORD - PUJ
Nonstop4h 45mArajet
Deal found 11/2$245
This Trip.com deal was found by Cheapflights users on 11/2. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/257:30 pmPUJ - ORD
Nonstop5h 10mMultiple Airlines
Tue 12/27:00 amORD - PUJ
Nonstop4h 37mMultiple Airlines
Deal found 11/2$249
This eDestinos deal was found by Cheapflights users on 11/1. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/14:15 pmSJU - MSP
Nonstop5h 54mSun Country Air
Sat 11/89:00 amMSP - SJU
Nonstop5h 14mSun Country Air
Deal found 11/1$260

Cheap flight deals from Caribbean to Wisconsin

Keep the following information in mind while searching for Caribbean to Wisconsin flight deals. Data was last updated November 3, 2025.

Round-trip from

$176
(Kiwi.com)

One-way from

$106
(eDestinos)

Popular in

July

Cheapest in

February

Average price

$363
From Caribbean to Wisconsin
Search Deals
One-way flight from Caribbean to Wisconsin
Search Deals
Highest demand for flights based on searches. 21% potential increase in price ($106 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Caribbean to Wisconsin 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 November 3, 2025.
Use the filters below to find and compare flights from Caribbean to Wisconsin that are best for you.

Fly from

Caribbean

Fly to

Wisconsin

Route

Depart

Return

Price

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 2/12

4:52 pm-8:20 pm

Nonstop5h 28m

Chicago O'Hare Intl

Mon 2/16

2:20 pm-9:00 pm

Nonstop4h 40m

$218

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Thu 1/29

6:27 pm-11:46 pm

1 stop7h 19m

Milwaukee-Mitchell

Mon 2/2

12:17 pm-8:57 pm

1 stop6h 40m

$235

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Sat 1/17

5:47 am-8:57 am

Nonstop5h 10m

Chicago O'Hare Intl

Sat 1/24

10:27 am-5:12 pm

Nonstop4h 45m

$243

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Fri 12/5

4:40 pm-9:45 pm

1 stop7h 05m

Milwaukee-Mitchell

Mon 12/8

11:05 am-10:05 pm

1 stop9h 00m

$274

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Wed 12/3

5:20 pm-3:24 pm

1 stop24h 04m

Chicago O'Hare Intl

Wed 12/10

8:45 am-5:25 pm

1 stop6h 40m

$274

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Sun 11/23

4:12 pm-7:23 pm

Nonstop5h 11m

Chicago O'Hare Intl

Tue 11/25

11:48 am-11:44 pm

1 stop9h 56m

$288

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Wed 12/17

5:56 pm-10:05 am

1 stop18h 09m

Madison Truax Field

Thu 1/1

4:45 pm-3:48 pm

2 stops21h 03m

$295

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Fri 12/19

6:15 pm-11:59 pm

1 stop7h 44m

Madison Truax Field

Mon 1/5

10:50 am-12:41 pm

2 stops23h 51m

$295

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Thu 12/18

3:58 pm-11:37 pm

1 stop9h 39m

Madison Truax Field

Mon 1/5

6:18 pm-6:22 pm

2 stops22h 04m

$295

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Thu 12/18

3:58 pm-11:37 pm

1 stop9h 39m

Madison Truax Field

Sat 1/3

4:45 pm-1:41 pm

2 stops18h 56m

$295

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/1

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

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

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

Currently, September is the cheapest month in which you can book a flight from Caribbean to Wisconsin (average of $113). Flying from Caribbean to Wisconsin in July is currently the most expensive (average of $290). 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 CB to WI?

Find hourly flight availability from Caribbean to Wisconsin. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated November 3, 2025.

It’s typically best to fly out from Caribbean to Wisconsin in the evening. Doing so could potentially save you 21% on the flight price compared to flying in the afternoon, which is usually more expensive.

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

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

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

Reviews of airlines servicing Wisconsin

Get insights into the airlines that provide service to Wisconsin. 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 Wisconsin. Reviews last updated November 3, 2025.
Get a feel of what it's like to fly with Southwest, Delta, and United Airlines from Caribbean to Wisconsin by reading reviews from past customers. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,238 reviews

Crew

8.6

Overall

8.0

Boarding

8.1

Comfort

8.0

Food

7.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,238 reviews
Southwest
8.0
Very good
4,238 reviews

Crew

8.6

Overall

8.0

Boarding

8.1

Comfort

8.0

Food

7.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Delta
7.9
Good
8,002 reviews
Southwest
8.0
Very good
4,238 reviews

Crew

8.6

Overall

8.0

Boarding

8.1

Comfort

8.0

Food

7.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
8,997 reviews
Southwest
8.0
Very good
4,238 reviews

Crew

8.6

Overall

8.0

Boarding

8.1

Comfort

8.0

Food

7.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
11,038 reviews
Southwest
8.0
Very good
4,238 reviews

Crew

8.6

Overall

8.0

Boarding

8.1

Comfort

8.0

Food

7.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

Related info for your journey

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

    Airlines like United Airlines, Delta, and Arajet fly from Caribbean to Wisconsin in about 5h 10m. The time it takes to get you to your destination can typically vary by up to 2h 09m. There are 1982 mi between Caribbean and Wisconsin. This flight may include one or multiple stops.

  • What are the cheapest airlines to fly from Caribbean to Wisconsin one-way?

    For one-way options, check prices for United Airlines. According to our data, you can fly for as low as $109. Users have also found prices from $118 and $118 on Southwest and Delta, respectively.

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

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

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

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

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

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

    Currently, September is the cheapest month in which you can book a flight from Caribbean to Wisconsin (average of $113). Flying from Caribbean to Wisconsin in July is currently the most expensive (average of $290). 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 Caribbean to Wisconsin

See prices for flight routes from nearby airports that may be better suited for you.
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Top 4 airlines flying from Caribbean to Wisconsin

Discover the top 4 airlines that operate flights from Caribbean to Wisconsin. 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 November 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$215Average$399FlexibilityNo cancel feeOn-time69%
DeltaCheapest$215Average$445FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$235Average$456FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$305Average$485FlexibilityNo cancel feeOn-time63%

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