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$189+ 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 8/18. Fares are subject to change and may not be available on all flights or dates of travel.
EVV — SJU
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
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 June 12, 2025.

Round-trip from

$456
(American Airlines)

One-way from

$189
(Kiwi.com)

Popular in

August

Cheapest in

September

Average price

$523
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. 9% potential increase in price ($52 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($27 potential savings vs. average RT price).
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Average for round-trip flights in June 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 June 12, 2025.

This American Airlines deal was found by Cheapflights users on 6/11. 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.
Wed 6/111:00 pmEVV - SJU
1 stop15h 06mAmerican Airlines
Wed 6/188:00 amSJU - EVV
1 stop14h 47mAmerican Airlines
Deal found 6/11$379
This American Airlines deal was found by Cheapflights users on 6/12. 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.
Sat 7/194:31 pmEVV - PUJ
2 stops19h 04mAmerican Airlines
Sat 7/263:25 pmPUJ - EVV
1 stop8h 59mAmerican Airlines
Deal found 6/12$456
This American Airlines deal was found by Cheapflights users on 6/10. 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.
Fri 10/175:35 pmEVV - STT
2 stops18h 15mAmerican Airlines
Fri 10/245:15 pmSTT - EVV
2 stops24h 23mAmerican Airlines
Deal found 6/10$509
This American Airlines deal was found by Cheapflights users on 6/11. 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.
Wed 6/254:31 pmEVV - MBJ
2 stops17h 00mAmerican Airlines
Sat 6/285:05 pmMBJ - EVV
2 stops17h 29mAmerican Airlines
Deal found 6/11$629

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 June 12, 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

EvansvillePunta Cana

EVV - PUJ

EVVPUJ

Evansville Dress Regional

Sat 7/19

4:31 pm-12:35 pm

2 stops19h 04m

Punta Cana

Sat 7/26

3:25 pm-11:24 pm

1 stop8h 59m

$456

EvansvilleSaint Thomas Island

EVV - STT

EVVSTT

Evansville Dress Regional

Fri 10/17

5:35 pm-12:50 pm

2 stops18h 15m

Saint Thomas Island Cyril E King

Fri 10/24

5:15 pm-4:38 pm

2 stops24h 23m

$509

EvansvilleMontego Bay

EVV - MBJ

EVVMBJ

Evansville Dress Regional

Wed 6/25

4:31 pm-9:31 am

2 stops17h 00m

Montego Bay Sangster Intl

Sat 6/28

5:05 pm-10:34 am

2 stops17h 29m

$629

EvansvilleSanto Domingo

EVV - SDQ

EVVSDQ

Evansville Dress Regional

Mon 8/18

7:19 pm-4:00 pm

2 stops19h 41m

$189

EvansvilleSan Juan

EVV - SJU

EVVSJU

Evansville Dress Regional

Tue 7/8

4:31 pm-5:06 am

2 stops11h 35m

$210

EvansvilleSanto Domingo

EVV - SDQ

EVVSDQ

Evansville Dress Regional

Mon 8/18

6:10 am-1:22 pm

1 stop6h 12m

$281

EvansvilleMontego Bay

EVV - MBJ

EVVMBJ

Evansville Dress Regional

Wed 6/25

5:30 am-3:20 pm

1 stop9h 50m

$289

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/12

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 June is currently the most expensive (average of $339). 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 June 12, 2025.
Delta
8.0
Very good
7,950 reviews

Food

7.3

Boarding

8.2

Entertainment

7.9

Overall

8.0

Comfort

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,950 reviews
Delta
8.0
Very good
7,950 reviews

Food

7.3

Boarding

8.2

Entertainment

7.9

Overall

8.0

Comfort

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,950 reviews

Food

7.3

Boarding

8.2

Entertainment

7.9

Overall

8.0

Comfort

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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 - Punta Cana, Evansville Dress Regional - Montego Bay Sangster Intl or Evansville Dress Regional - San Juan Luis Munoz Marin Intl 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 June is currently the most expensive (average of $339). 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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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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$284Average$639FlexibilityNo cancel feeOn-time71%
DeltaCheapest$371Average$704FlexibilityNo cancel feeOn-timeN/A

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