Wisconsin

$87+ 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 2/24. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — MKE
Mar 7 — Mar 141
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Cheap 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 February 5, 2026.

This CheapOair deal was found by Cheapflights users on 2/2. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/2611:52 am
SJU
-
ORD
1 stop8h 26m
Spirit Airlines
Tue 3/35:15 am
ORD
-
SJU
1 stop8h 16m
Spirit Airlines
Deal found 2/2$136
This Expedia deal was found by Cheapflights users on 2/2. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/2612:32 pm
SJU
-
ORD
Nonstop5h 16m
Spirit Airlines
Mon 3/212:17 pm
ORD
-
SJU
Nonstop4h 32m
Spirit Airlines
Deal found 2/2$141
This Cheapflightsfares deal was found by Cheapflights users on 2/5. 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.
Fri 3/611:52 am
SJU
-
ORD
1 stop8h 26m
Spirit Airlines
Tue 3/1012:22 pm
ORD
-
SJU
Nonstop4h 32m
Spirit Airlines
Deal found 2/5$145
This Cheapflightsfares deal was found by Cheapflights users on 2/5. 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.
Wed 2/111:22 pm
SJU
-
ORD
Nonstop5h 15m
Spirit Airlines
Wed 3/412:17 pm
ORD
-
SJU
Nonstop4h 32m
Spirit Airlines
Deal found 2/5$147
This Expedia deal was found by Cheapflights users on 2/1. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/51:22 pm
SJU
-
ORD
Nonstop5h 15m
Spirit Airlines
Sat 2/712:17 pm
ORD
-
SJU
Nonstop4h 32m
Spirit Airlines
Deal found 2/1$149
This Orbitz deal was found by Cheapflights users on 2/2. 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.
Fri 2/2711:52 am
SJU
-
ORD
1 stop8h 26m
Spirit Airlines
Mon 3/212:17 pm
ORD
-
SJU
Nonstop4h 32m
Spirit Airlines
Deal found 2/2$150
This Expedia deal was found by Cheapflights users on 2/3. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/312:32 pm
SJU
-
ORD
Nonstop5h 16m
Spirit Airlines
Sat 3/712:17 pm
ORD
-
SJU
Nonstop4h 32m
Spirit Airlines
Deal found 2/3$151
This Expedia deal was found by Cheapflights users on 2/2. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/1212:32 pm
SJU
-
ORD
Nonstop5h 16m
Spirit Airlines
Tue 2/2412:17 pm
ORD
-
SJU
Nonstop4h 32m
Spirit Airlines
Deal found 2/2$152
This Cheapflightsfares deal was found by Cheapflights users on 2/4. 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 2/101:22 pm
SJU
-
ORD
Nonstop5h 15m
Spirit Airlines
Sat 2/1412:17 pm
ORD
-
SJU
Nonstop4h 32m
Spirit Airlines
Deal found 2/4$156
This Orbitz deal was found by Cheapflights users on 2/2. 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.
Tue 2/243:53 am
SJU
-
MKE
1 stop13h 51m
Frontier
Sat 2/287:47 pm
MKE
-
SJU
1 stop27h 07m
Frontier
Deal found 2/2$174
This Priceline deal was found by Cheapflights users on 2/4. 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 2/173:53 am
SJU
-
MKE
1 stop29h 47m
Frontier
Mon 2/238:11 pm
MKE
-
SJU
1 stop28h 42m
Frontier
Deal found 2/4$202
This Trip.com deal was found by Cheapflights users on 2/4. 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.
Thu 2/196:00 am
SJU
-
MKE
1 stop29h 43m
Frontier
Mon 2/238:11 pm
MKE
-
SJU
1 stop11h 43m
Frontier
Deal found 2/4$213

Find flight deals from Caribbean to Wisconsin

Keep the following information in mind while searching for Caribbean to Wisconsin flight deals. Data was last updated February 5, 2026.

Round-trip from

$136
(CheapOair)

One-way from

$87
(Frontier)

Popular in

July

Cheapest in

February

Average price

$279
From Caribbean to Wisconsin
One-way flight from Caribbean to Wisconsin
Highest demand for flights based on searches. 23% potential increase in price ($112 potential increase over avg. RT price).
Cheapest flight prices on average. 2% potential price decrease ($11 potential savings vs. average RT price).
Average for round-trip flights in February 2026

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 February 5, 2026.
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

12:32 pm-3:48 pm

Nonstop5h 16m

Chicago O'Hare Intl

Tue 2/24

12:17 pm-6:49 pm

Nonstop4h 32m

$155

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 3/5

11:52 am-6:18 pm

1 stop8h 26m

Chicago O'Hare Intl

Sun 3/8

8:16 pm-2:31 pm

1 stop17h 15m

$175

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Tue 4/7

11:03 am-9:50 am

1 stop23h 47m

Chicago O'Hare Intl

Tue 4/14

10:55 am-11:58 pm

1 stop12h 03m

$196

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Thu 2/19

6:00 am-9:43 am

1 stop29h 43m

Milwaukee-Mitchell

Mon 2/23

8:11 pm-9:54 am

1 stop11h 43m

$202

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Sat 2/14

11:52 am-7:47 pm

1 stop9h 55m

Chicago O'Hare Intl

Sun 2/22

12:17 pm-6:49 pm

Nonstop4h 32m

$204

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Mon 3/9

10:52 am-6:18 pm

1 stop8h 26m

Chicago O'Hare Intl

Thu 3/12

3:21 pm-12:29 am

1 stop8h 08m

$205

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Tue 3/31

1:29 am-5:45 am

Nonstop5h 16m

Chicago O'Hare Intl

Thu 4/9

1:02 pm-12:53 am

1 stop10h 51m

$206

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Fri 3/6

7:00 am-5:03 pm

1 stop12h 03m

Chicago O'Hare Intl

Sun 3/8

7:00 am-2:31 pm

1 stop6h 31m

$206

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 2/26

12:32 pm-3:48 pm

Nonstop5h 16m

Chicago O'Hare Intl

Sun 3/1

12:17 pm-6:49 pm

Nonstop4h 32m

$209

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Wed 4/22

12:22 pm-4:37 pm

Nonstop5h 15m

Chicago O'Hare Intl

Sat 4/25

8:00 am-3:37 pm

1 stop6h 37m

$211

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/2

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 June is currently the most expensive (average of $355). 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 February 5, 2026.

When flying from Caribbean to Wisconsin, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 February 5, 2026.
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.

Boarding

8.1

Overall

8.0

Food

7.0

Crew

8.6

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

Boarding

8.1

Overall

8.0

Food

7.0

Crew

8.6

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

Boarding

8.1

Overall

8.0

Food

7.0

Crew

8.6

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

Boarding

8.1

Overall

8.0

Food

7.0

Crew

8.6

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

Boarding

8.1

Overall

8.0

Food

7.0

Crew

8.6

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

Boarding

8.1

Overall

8.0

Food

7.0

Crew

8.6

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

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 Spirit Airlines, Frontier, and American Airlines fly from Caribbean to Wisconsin in about 5h 16m. The time it takes to get you to your destination can typically vary by up to 24h 27m. There are 2073 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 Frontier. According to our data, you can fly for as low as $80. Users have also found prices from $112 and $118 on Southwest and United Airlines, 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 June is currently the most expensive (average of $355). 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 Caribbean to Wisconsin

See prices for flight routes from nearby airports that may be better suited for you.

Top 5 airlines flying from Caribbean to Wisconsin

Discover the top 5 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 February 5, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$112Average$456FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$140Average$299FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$215Average$356FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$235Average$468FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$256Average$439FlexibilityNo cancel feeOn-time63%

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