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$57+ 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 12/9. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SJU
Nov 5 — Nov 121
1 adult
Tue 11/5
Tue 11/12
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Find 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 October 31, 2024.

This FlightHub deal was found by Cheapflights users on 10/30. 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.
Fri 12/66:07 pmORD - SJU
1 stop21h 16mMultiple Airlines
Wed 12/112:17 pmSJU - ORD
Nonstop5h 30mMultiple Airlines
Deal found 10/30$169
This FareScan deal was found by Cheapflights users on 10/31. 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 FareScan is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/39:10 pmORD - SJU
1 stop12h 51mSpirit Airlines
Tue 12/1010:34 amSJU - ORD
1 stop11h 41mSpirit Airlines
Deal found 10/31$171
This FlightHub deal was found by Cheapflights users on 10/30. 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.
Thu 11/146:30 amORD - SJU
1 stop17h 19mFrontier
Sun 11/1710:12 pmSJU - ORD
1 stop15h 40mFrontier
Deal found 10/30$175
This CheapOair deal was found by Cheapflights users on 10/30. 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 12/51:02 pmMSP - SJU
2 stops11h 40mMultiple Airlines
Mon 12/96:25 amSJU - MSP
1 stop12h 06mMultiple Airlines
Deal found 10/30$199
This Frontier deal was found by Cheapflights users on 10/31. 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 11/47:12 pmMSP - SJU
1 stop7h 36mFrontier
Thu 11/1410:18 pmSJU - MSP
1 stop12h 27mFrontier
Deal found 10/31$238
This FareScan deal was found by Cheapflights users on 10/31. 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 FareScan is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/611:44 amMSP - SJU
2 stops27h 59mSpirit Airlines
Thu 12/123:20 amSJU - MSP
1 stop10h 37mSpirit Airlines
Deal found 10/31$246
This Mytrip deal was found by Cheapflights users on 10/31. 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.
Sat 11/165:00 amORD - PUJ
1 stop8h 46mMultiple Airlines
Wed 11/204:37 pmPUJ - ORD
Nonstop5h 28mMultiple Airlines
Deal found 10/31$287
This Mytrip deal was found by Cheapflights users on 10/29. 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 11/1411:10 amORD - STT
2 stops21h 38mSpirit Airlines
Tue 11/1911:43 amSTT - ORD
1 stop8h 58mSpirit Airlines
Deal found 10/29$287
This Cheapflightsfares deal was found by Cheapflights users on 10/31. 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.
Sat 12/76:00 amORD - PUJ
Nonstop4h 29mFrontier
Thu 12/126:45 pmPUJ - ORD
Nonstop5h 14mFrontier
Deal found 10/31$288
This JetBlue deal was found by Cheapflights users on 10/30. 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.
Sun 12/88:51 amORD - SJU
1 stop7h 44mJetBlue
Tue 12/107:00 amSJU - ORD
1 stop10h 53mJetBlue
Deal found 10/30$289
This American Airlines deal was found by Cheapflights users on 10/30. 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.
Mon 12/97:00 amORD - PUJ
1 stop7h 05mAmerican Airlines
Thu 12/125:50 pmPUJ - ORD
1 stop8h 24mAmerican Airlines
Deal found 10/30$336
This United Airlines deal was found by Cheapflights users on 10/30. 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 Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/910:43 amORD - PUJ
Nonstop4h 28mUnited Airlines
Mon 12/165:25 pmPUJ - ORD
1 stop7h 55mUnited Airlines
Deal found 10/30$339

Find flights from Wisconsin to Caribbean within your budget

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 2,570,725 searches. Data last updated October 31, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

MinneapolisSan Juan

MSP - SJU

MSPSJU

Minneapolis St Paul

Fri 1/3

7:25 pm-10:35 am

1 stop13h 10m

$84

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 12/10

8:02 pm-5:43 pm

1 stop19h 41m

$89

MinneapolisSan Juan

MSP - SJU

MSPSJU

Minneapolis St Paul

Mon 12/9

7:14 am-5:43 pm

1 stop8h 29m

$110

MinneapolisSan Juan

MSP - SJU

MSPSJU

Minneapolis St Paul

Sat 12/14

8:47 am-4:01 pm

Nonstop5h 14m

$142

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 12/7

8:51 am-7:19 pm

1 stop8h 28m

$143

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Mon 12/9

5:10 am-4:45 pm

1 stop9h 35m

$160

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Wed 1/1

6:20 am-4:52 pm

1 stop8h 32m

$165

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sun 1/26

4:01 pm-2:38 am

1 stop8h 37m

$84

ChicagoOranjestad

ORD - AUA

ORDAUA

Chicago O'Hare Intl

Wed 1/29

1:35 pm-10:00 am

1 stop18h 25m

$172

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Mon 11/11

10:43 am-5:11 pm

Nonstop4h 28m

$176

Flights are sorted by cheapest first

Deals found on 10/30

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.

Travel insights for flights from Wisconsin to Caribbean

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

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

Currently, September is the cheapest month in which you can book a flight from Wisconsin to Caribbean (average of $254). Flying from Wisconsin to Caribbean in March is currently the most expensive (average of $335). 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 October 31, 2024.

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.

Rainfall in Caribbean by month

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

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

Temperature in Caribbean by month

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

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

Get insights into the airlines that provide service to Caribbean. 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. Reviews last updated October 31, 2024.
Southwest
8.1
Very good
5,116 reviews

Boarding

8.3

Crew

8.7

Entertainment

7.7

Overall

8.1

Food

7.2

Comfort

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Southwest
8.1
Very good
5,116 reviews
Southwest
8.1
Very good
5,116 reviews

Boarding

8.3

Crew

8.7

Entertainment

7.7

Overall

8.1

Food

7.2

Comfort

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Delta
8.0
Very good
8,835 reviews
Southwest
8.1
Very good
5,116 reviews

Boarding

8.3

Crew

8.7

Entertainment

7.7

Overall

8.1

Food

7.2

Comfort

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Alaska Airlines
8.0
Very good
9,420 reviews
Southwest
8.1
Very good
5,116 reviews

Boarding

8.3

Crew

8.7

Entertainment

7.7

Overall

8.1

Food

7.2

Comfort

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Copa Airlines
7.8
Good
1,885 reviews
Southwest
8.1
Very good
5,116 reviews

Boarding

8.3

Crew

8.7

Entertainment

7.7

Overall

8.1

Food

7.2

Comfort

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

JetBlue
7.5
Good
3,514 reviews
Southwest
8.1
Very good
5,116 reviews

Boarding

8.3

Crew

8.7

Entertainment

7.7

Overall

8.1

Food

7.2

Comfort

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

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.

  • Can I find flights from Wisconsin to Caribbean for under $200 on Cheapflights?

    Yes, there are multiple flights from Wisconsin to Caribbean for under $200. The cheapest flight booked recently is on Spirit Airlines for just $126, but on average you can expect to pay $266.

  • Are there nonstop flights from Wisconsin to Caribbean for under $200 on Cheapflights?

    Cheapflights has at least 20 direct flights from Wisconsin to Caribbean under $200. A good price for a nonstop flight from Wisconsin to Caribbean is less than $450.

  • Are there last-minute flights available from Wisconsin to Caribbean for under $200?

    There are currently 20+ open flights from Wisconsin to Caribbean within the next 7 days for less than $200.

  • 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 $57. Users have also found prices from $68 and $114 on Spirit Airlines and Sun Country Air, respectively.

  • What does MKE to SJU mean?

    These are just IATA (International Air Transport Association) codes. They are used in aviation to identify and differentiate airports. That’s why a Milwaukee-Mitchell Airport to San Juan Luis Munoz Marin Intl Airport flight would often be abbreviated as a MKE to SJU flight. Punta Cana Airport (PUJ), Santo Domingo Las Americas Airport (SDQ), Montego Bay Sangster Intl Airport (MBJ), Oranjestad Reina Beatrix Airport (AUA), Nassau Intl Airport (NAS) are some additional IATA codes for airports related to your trip.

  • Can I find deals for flights from Wisconsin to Caribbean that include extra baggage allowance?

    The amount of baggage you can bring on your Wisconsin to Caribbean flight depends on the airline and the type of fare you've chosen. After entering your flight details, you'll be able to view the specific baggage policies for each deal in the search results. Keep in mind that certain deals may offer additional baggage allowance.

  • Can I find deals on flights from Wisconsin to Caribbean with specific airlines?

    Yes, Cheapflights allows you to browse and filter Wisconsin to Caribbean flight deals by airline. After entering your origin and destination, use the available filters to view flights offered by airlines.

  • 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.

  • Can I find deals for flights from Wisconsin to Caribbean that allow pets onboard?

    Many airlines flying from Wisconsin to Caribbean offer the option to travel with pets. After selecting a flight deal, you can find more information about the airline's pet policy on their official website or by contacting the airline directly. Please note that additional fees and restrictions may apply.

  • Can I find deals on last-minute flights from Wisconsin to Caribbean?

    Yes, you can often find last-minute deals on Wisconsin to Caribbean flights on Cheapflights. However, these deals can vary and may not always be available. We recommend checking back frequently or signing up for price alerts for the most up-to-date deals.

  • How recently were the Wisconsin to Caribbean flight deals updated?

    The Wisconsin to Caribbean flight deals you see on this page were last updated on 10/31.

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

    Currently, September is the cheapest month in which you can book a flight from Wisconsin to Caribbean (average of $254). Flying from Wisconsin to Caribbean in March is currently the most expensive (average of $335). 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 Wisconsin to Caribbean

See prices for flight routes from nearby airports that may be better suited for you.
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Top 8 airlines flying from Wisconsin to Caribbean

Discover the top 8 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 2,570,725 searches. Data last updated October 31, 2024.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$175Average$404FlexibilityNo cancel feeOn-time65%
FrontierCheapest$230Average$352FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$257Average$618FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$280Average$678FlexibilityNo cancel feeOn-time69%
DeltaCheapest$284Average$650FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$325Average$657FlexibilityNo cancel feeOn-time63%
JetBlueCheapest$360Average$608FlexibilityNo cancel feeOn-time62%
Sun Country AirCheapest$398Average$671FlexibilityNo cancel feeOn-time83%
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