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$185+ Cheap flights from Evansville (EVV) 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 4/14. Fares are subject to change and may not be available on all flights or dates of travel.
EVV — SJU
apr. 5 — apr. 121
lør. 4/5
lør. 4/12
1 adult, Economy
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Cheap flight deals from Evansville to Caribbean

Keep the following information in mind while searching for Evansville to Caribbean flight deals. Data was last updated marts 31, 2025.

Round-trip from

$345
(Delta)

One-way from

$185
(American Airlines)

Popular in

January

Cheapest in

September

Average price

$561
From Evansville Dress Regional to Caribbean
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One-way flight from Evansville Dress Regional to Caribbean
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Highest demand for flights based on searches. 1% potential increase in price ($8 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in March 2025
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Find flight deals from Evansville to Caribbean

Cheapest flights from Evansville to Caribbean
Explore the most affordable flight options available from Evansville to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on marts 31, 2025.

This Delta deal was found by Cheapflights users on 3/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lør. 5/241:18 pmEVV - SJU
1 stop8h 29mDelta
ons. 5/282:31 pmSJU - EVV
1 stop6h 49mDelta
Deal found 3/30$345
This American Airlines deal was found by Cheapflights users on 3/30. 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.
ons. 6/114:31 pmEVV - SJU
1 stop6h 37mAmerican Airlines
ons. 6/186:55 pmSJU - EVV
2 stops16h 39mAmerican Airlines
Deal found 3/30$382
This Delta deal was found by Cheapflights users on 3/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
man. 4/286:20 amEVV - PUJ
1 stop7h 10mDelta
man. 5/53:55 pmPUJ - EVV
1 stop7h 26mDelta
Deal found 3/30$457
This American Airlines deal was found by Cheapflights users on 3/30. 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.
man. 4/284:27 pmEVV - PUJ
2 stops17h 27mAmerican Airlines
man. 5/53:16 pmPUJ - EVV
2 stops19h 44mAmerican Airlines
Deal found 3/30$459
This Mytrip deal was found by Cheapflights users on 3/29. 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.
man. 4/146:21 pmEVV - SJU
1 stop20h 54mMultiple Airlines
tor. 4/172:12 amSJU - EVV
2 stops16h 29mMultiple Airlines
Deal found 3/29$568
This American Airlines deal was found by Cheapflights users on 3/30. 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.
lør. 6/284:31 pmEVV - MBJ
2 stops19h 39mAmerican Airlines
lør. 7/52:26 pmMBJ - EVV
1 stop26h 12mAmerican Airlines
Deal found 3/30$613

Cheapflights Fare Finder

Customize your flight search to find flights from Evansville 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 marts 31, 2025.
Use the filters below to find and compare flights from Evansville to Caribbean that are best for you.

Fly from

Evansville

Fly to

Caribbean

Route

Depart

Return

Price

EvansvilleSan Juan

EVV - SJU

EVVSJU

Evansville Dress Regional

lør. 5/24

1:18 pm-10:47 pm

1 stop8h 29m

San Juan Luis Munoz Marin Intl

ons. 5/28

2:31 pm-8:20 pm

1 stop6h 49m

$345

EvansvilleSan Juan

EVV - SJU

EVVSJU

Evansville Dress Regional

ons. 6/11

4:31 pm-12:08 am

1 stop6h 37m

San Juan Luis Munoz Marin Intl

ons. 6/18

6:55 pm-10:34 am

2 stops16h 39m

$382

EvansvillePunta Cana

EVV - PUJ

EVVPUJ

Evansville Dress Regional

man. 4/28

6:20 am-2:30 pm

1 stop7h 10m

Punta Cana

man. 5/5

3:55 pm-10:21 pm

1 stop7h 26m

$457

EvansvillePunta Cana

EVV - PUJ

EVVPUJ

Evansville Dress Regional

man. 4/28

4:27 pm-10:54 am

2 stops17h 27m

Punta Cana

man. 5/5

3:16 pm-10:00 am

2 stops19h 44m

$459

EvansvilleSan Juan

EVV - SJU

EVVSJU

Evansville Dress Regional

man. 4/14

6:21 pm-4:15 pm

1 stop20h 54m

San Juan Luis Munoz Marin Intl

tor. 4/17

2:12 am-5:41 pm

2 stops16h 29m

$568

EvansvilleMontego Bay

EVV - MBJ

EVVMBJ

Evansville Dress Regional

lør. 6/28

4:31 pm-12:10 pm

2 stops19h 39m

Montego Bay Sangster Intl

lør. 7/5

2:26 pm-4:38 pm

1 stop26h 12m

$613

EvansvilleSan Juan

EVV - SJU

EVVSJU

Evansville Dress Regional

man. 4/14

4:27 pm-5:00 am

2 stops11h 33m

$185

EvansvilleSan Juan

EVV - SJU

EVVSJU

Evansville Dress Regional

man. 4/14

6:21 pm-5:33 pm

3 stops22h 12m

$309

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/29

Best time to book a flight from Evansville to Caribbean

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

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

Currently, September is the cheapest month in which you can book a flight from Evansville to Caribbean (average of $254). Flying from Evansville to Caribbean in December is currently the most expensive (average of $336). 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.

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 marts 31, 2025.
Delta
8.0
Very good
7,899 reviews

Comfort

8.0

Overall

8.0

Crew

8.5

Food

7.3

Entertainment

7.9

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Delta
8.0
Very good
7,899 reviews
Delta
8.0
Very good
7,899 reviews

Comfort

8.0

Overall

8.0

Crew

8.5

Food

7.3

Entertainment

7.9

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,899 reviews

Comfort

8.0

Overall

8.0

Crew

8.5

Food

7.3

Entertainment

7.9

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

Related info for your journey

Find useful and relevant information for your journey from Evansville to Caribbean. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Evansville to Caribbean?

    Most people fly from Evansville Dress Regional (EVV) if they book a flight from Evansville to Caribbean. Evansville Dress Regional is conveniently located just 4.4 mi from Evansville’s city center.

  • What are the most popular routes from Evansville to Caribbean?

    Most travelers choose Evansville Dress Regional - San Juan Luis Munoz Marin Intl, Evansville Dress Regional - Montego Bay Sangster Intl or Evansville Dress Regional - Punta Cana when deciding on the best route from Evansville to Caribbean.

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

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

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

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

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

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

    Currently, September is the cheapest month in which you can book a flight from Evansville to Caribbean (average of $254). Flying from Evansville to Caribbean in December is currently the most expensive (average of $336). 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 Evansville to Caribbean

See prices for flight routes from nearby airports that may be better suited for you.
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Top 2 airlines flying from Evansville to Caribbean

Discover the top 2 airlines that operate flights from Evansville 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 marts 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$284Average$649FlexibilityNo cancel feeOn-time71%
DeltaCheapest$371Average$797FlexibilityNo cancel feeOn-timeN/A
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