Caribbean Islands

$90+ Cheap flights from Wisconsin to Caribbean Islands

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 2/18. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SJU
12月 27 — 1月 31
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Cheap flight deals from Wisconsin to Caribbean Islands

Discover tips and strategies to find the most affordable flight options for your journey from Wisconsin (USWI) to Caribbean Islands (zzEPX). 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 12月 22, 2024.

Round-trip from

$162
(Kiwi.com)

One-way from

$90
(Trip.com)
From Wisconsin to Caribbean Islands
One-way flight from Wisconsin to Caribbean Islands

Find flight deals from Wisconsin to Caribbean Islands

Cheapest flights from Wisconsin to Caribbean Islands
Explore the most affordable flight options available from Wisconsin to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 12月 22, 2024.

This eDestinos deal was found by Cheapflights users on 12/21. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
月 12/309:35 pmORD - SJU
1 stop15h 44mSpirit Airlines
火 1/149:26 pmSJU - ORD
Nonstop5h 25mSpirit Airlines
Deal found 12/21$244
This eDestinos deal was found by Cheapflights users on 12/21. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
月 12/309:35 pmORD - SJU
1 stop15h 44mMultiple Airlines
火 1/148:45 amSJU - ORD
2 stops29h 02mMultiple Airlines
Deal found 12/21$330
This Priceline deal was found by Cheapflights users on 12/21. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
火 12/3111:27 amMSP - SJU
1 stop13h 22mMultiple Airlines
月 4/211:10 amSJU - MSP
1 stop13h 07mMultiple Airlines
Deal found 12/21$375
This FlightHub deal was found by Cheapflights users on 12/22. 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.
日 12/291:30 pmMSP - SJU
1 stop10h 05mSpirit Airlines
火 1/288:40 pmSJU - MSP
2 stops18h 17mSpirit Airlines
Deal found 12/22$393
This Kiwi.com deal was found by Cheapflights users on 12/22. 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.
火 12/315:11 pmORD - STT
1 stop15h 28mSpirit Airlines
木 1/911:51 amSTT - ORD
1 stop10h 22mSpirit Airlines
Deal found 12/22$398
This American Airlines deal was found by Cheapflights users on 12/22. 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.
火 12/318:17 amORD - PUJ
Nonstop4h 30mAmerican Airlines
土 1/115:40 pmPUJ - ORD
1 stop17h 05mAmerican Airlines
Deal found 12/22$414
This American Airlines deal was found by Cheapflights users on 12/21. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
水 12/257:00 amORD - SJU
1 stop14h 10mAmerican Airlines
金 12/2712:51 pmSJU - ORD
1 stop11h 01mAmerican Airlines
Deal found 12/21$424
This Delta deal was found by Cheapflights users on 12/22. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
月 12/305:40 amORD - PUJ
1 stop8h 54mDelta
火 12/315:59 pmPUJ - ORD
1 stop7h 57mDelta
Deal found 12/22$448
This FlightHub deal was found by Cheapflights users on 12/22. 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.
木 12/262:19 pmORD - SJU
1 stop8h 22mFrontier
月 12/304:00 pmSJU - ORD
1 stop29h 14mFrontier
Deal found 12/22$455
This United deal was found by Cheapflights users on 12/22. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
月 12/302:20 pmORD - SJU
Nonstop4h 35mUnited Airlines
金 1/172:05 amSJU - ORD
1 stop9h 23mUnited Airlines
Deal found 12/22$458
This Frontier deal was found by Cheapflights users on 12/22. 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.
日 12/2910:14 pmORD - PUJ
1 stop11h 32mFrontier
月 12/301:59 pmPUJ - ORD
1 stop10h 13mFrontier
Deal found 12/22$465
This Cheapflightsfares deal was found by Cheapflights users on 12/22. 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.
水 12/256:47 amMSP - SJU
Nonstop5h 24mSun Country Air
土 12/284:50 pmSJU - MSP
Nonstop5h 55mSun Country Air
Deal found 12/22$468

Find flights from Wisconsin to Caribbean Islands within your budget

Customize your flight search to find flights from Wisconsin to Caribbean Islands 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 12月 22, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

土 1/11

1:44 pm-8:21 pm

Nonstop4h 37m

San Juan Luis Munoz Marin Intl

金 1/17

9:26 pm-12:51 am

Nonstop5h 25m

$162

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

日 1/19

1:44 pm-8:21 pm

Nonstop4h 37m

San Juan Luis Munoz Marin Intl

水 1/22

9:15 pm-9:27 am

1 stop14h 12m

$163

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

日 1/12

4:11 pm-2:21 am

1 stop8h 10m

San Juan Luis Munoz Marin Intl

水 1/15

9:15 pm-9:27 am

1 stop14h 12m

$168

MinneapolisSan Juan

MSP - SJU

MSPSJU

Minneapolis St Paul

火 2/18

10:39 am-9:35 am

1 stop20h 56m

San Juan Luis Munoz Marin Intl

月 2/24

8:43 pm-9:39 am

1 stop14h 56m

$224

MinneapolisSan Juan

MSP - SJU

MSPSJU

Minneapolis St Paul

月 1/27

10:14 am-2:19 am

1 stop14h 05m

San Juan Luis Munoz Marin Intl

火 2/4

8:40 pm-12:57 pm

2 stops18h 17m

$228

MinneapolisSan Juan

MSP - SJU

MSPSJU

Minneapolis St Paul

月 1/27

6:00 am-12:57 am

2 stops16h 57m

San Juan Luis Munoz Marin Intl

金 1/31

10:16 am-11:31 pm

2 stops15h 15m

$234

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

日 1/12

11:15 am-10:22 pm

1 stop9h 07m

San Juan Luis Munoz Marin Intl

月 1/13

2:05 am-9:40 am

1 stop9h 35m

$259

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

日 2/2

5:11 am-3:45 pm

1 stop8h 34m

Punta Cana

水 2/12

4:48 pm-11:58 pm

1 stop9h 10m

$259

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

金 1/24

8:12 pm-11:10 am

1 stop12h 58m

Punta Cana

土 2/1

4:50 pm-11:32 pm

1 stop8h 42m

$261

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

金 2/7

8:12 pm-11:10 am

1 stop12h 58m

Punta Cana

水 2/12

2:29 pm-10:06 pm

2 stops33h 37m

$276

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/22

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

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

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

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

Currently, September is the cheapest month in which you can book a flight from Wisconsin to Caribbean Islands (average of $254). Flying from Wisconsin to Caribbean Islands in March is currently the most expensive (average of $380). 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 EPX?

Find hourly flight availability from Wisconsin to Caribbean Islands. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated 12月 22, 2024.

When flying from Wisconsin to Caribbean Islands, 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 Islands by month

Plan your trip to Caribbean Islands by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Caribbean Islands 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 Islands when rainfall is around 2.2 in.

Temperature in Caribbean Islands by month

Plan your trip to Caribbean Islands by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Caribbean Islands, 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 Islands

Get insights into the airlines that provide service to Caribbean Islands. 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 Islands. Reviews last updated 12月 22, 2024.
Peruse reviews from past customers who have flown with Spirit Airlines, Frontier and United Airlines from Wisconsin to Caribbean Islands to help guide your decision. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
8.1
Very good
4,804 reviews

Overall

8.1

Crew

8.7

Entertainment

7.7

Food

7.2

Boarding

8.2

Comfort

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

8.1
Very good
4,804 reviews
8.1
Very good
4,804 reviews

Overall

8.1

Crew

8.7

Entertainment

7.7

Food

7.2

Boarding

8.2

Comfort

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

8.0
Very good
8,594 reviews
8.1
Very good
4,804 reviews

Overall

8.1

Crew

8.7

Entertainment

7.7

Food

7.2

Boarding

8.2

Comfort

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

8.0
Very good
9,537 reviews
8.1
Very good
4,804 reviews

Overall

8.1

Crew

8.7

Entertainment

7.7

Food

7.2

Boarding

8.2

Comfort

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

7.7
Good
1,713 reviews
8.1
Very good
4,804 reviews

Overall

8.1

Crew

8.7

Entertainment

7.7

Food

7.2

Boarding

8.2

Comfort

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

7.4
Good
9,028 reviews
8.1
Very good
4,804 reviews

Overall

8.1

Crew

8.7

Entertainment

7.7

Food

7.2

Boarding

8.2

Comfort

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Related info for your journey

Find useful and relevant information for your journey from Wisconsin to Caribbean Islands. 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 Islands one-way?

    For one-way options, check prices for Frontier. According to our data, you can fly for as low as $90. Users have also found prices from $91 and $113 on Spirit Airlines and United Airlines, respectively.

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

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

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

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

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

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

    Currently, September is the cheapest month in which you can book a flight from Wisconsin to Caribbean Islands (average of $254). Flying from Wisconsin to Caribbean Islands in March is currently the most expensive (average of $380). 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.

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Alternative routes for Wisconsin to Caribbean Islands

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

Top 8 airlines flying from Wisconsin to Caribbean Islands

Discover the top 8 airlines that operate flights from Wisconsin to Caribbean Islands. 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 12月 22, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$146Average$352FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$168Average$409FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$258Average$647FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$274Average$651FlexibilityNo cancel feeOn-time69%
DeltaCheapest$284Average$665FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$360Average$573FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$379Average$725FlexibilityNo cancel feeOn-time63%
Sun Country AirCheapest$498Average$670FlexibilityNo cancel feeOn-time83%
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