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$197+ 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 12/22. Fares are subject to change and may not be available on all flights or dates of travel.
EVV — SJU
Jan 11 — Jan 181
Sun 1/11
Sun 1/18
1 adult, Economy
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Cheap 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 December 12, 2025.

This American Airlines deal was found by Cheapflights users on 12/10. 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.
Thu 12/185:10 amEVV - SJU
1 stop14h 55mAmerican Airlines
Mon 12/224:03 pmSJU - EVV
1 stop8h 36mAmerican Airlines
Deal found 12/10$459
This Kiwi.com deal was found by Cheapflights users on 12/9. 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.
Mon 12/2912:22 pmEVV - SJU
2 stops22h 07mMultiple Airlines
Mon 1/56:00 amSJU - EVV
1 stop7h 42mMultiple Airlines
Deal found 12/9$654
This American Airlines deal was found by Cheapflights users on 12/10. 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.
Sat 12/274:51 pmEVV - PUJ
1 stop21h 51mAmerican Airlines
Thu 1/12:27 pmPUJ - EVV
1 stop11h 21mAmerican Airlines
Deal found 12/10$713
This American Airlines deal was found by Cheapflights users on 12/9. 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 12/295:10 amEVV - SJU
2 stops10h 57mAmerican Airlines
Mon 1/55:24 amSJU - EVV
2 stops12h 57mAmerican Airlines
Deal found 12/9$1,248
This American Airlines deal was found by Cheapflights users on 12/9. 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 12/205:10 amEVV - PUJ
1 stop6h 17mAmerican Airlines
Fri 1/25:23 pmPUJ - EVV
2 stops19h 18mAmerican Airlines
Deal found 12/9$1,555

Find flight deals from Evansville to Caribbean

Keep the following information in mind while searching for Evansville to Caribbean flight deals. Data was last updated December 12, 2025.

Round-trip from

$235
(American Airlines)

One-way from

$197
(Kiwi.com)

Popular in

January

Cheapest in

October

Average price

$665
From Evansville Dress Regional to Caribbean
Search Deals
One-way flight from Evansville Dress Regional to Caribbean
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($59 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($17 potential savings vs. average RT price).
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Average for round-trip flights in December 2025
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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 December 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

EvansvilleSan Juan

EVV - SJU

EVVSJU

Evansville Dress Regional

Sat 2/28

6:54 pm-11:41 am

1 stop14h 47m

San Juan Luis Munoz Marin Intl

Tue 3/3

6:00 am-3:58 pm

1 stop11h 58m

$235

EvansvilleSan Juan

EVV - SJU

EVVSJU

Evansville Dress Regional

Sat 1/17

7:10 am-9:39 pm

1 stop12h 29m

San Juan Luis Munoz Marin Intl

Thu 1/22

8:20 am-10:50 pm

1 stop16h 30m

$294

EvansvilleSan Juan

EVV - SJU

EVVSJU

Evansville Dress Regional

Sat 1/17

7:10 am-9:39 pm

1 stop12h 29m

San Juan Luis Munoz Marin Intl

Mon 1/26

11:38 am-10:50 pm

2 stops13h 12m

$294

EvansvilleSan Juan

EVV - SJU

EVVSJU

Evansville Dress Regional

Sat 1/17

7:10 am-9:39 pm

1 stop12h 29m

San Juan Luis Munoz Marin Intl

Sun 1/25

8:20 am-10:50 pm

1 stop16h 30m

$348

EvansvillePunta Cana

EVV - PUJ

EVVPUJ

Evansville Dress Regional

Mon 1/19

6:13 am-3:29 pm

1 stop7h 16m

Punta Cana

Sat 1/24

3:43 pm-11:37 am

2 stops21h 54m

$434

EvansvilleMontego Bay

EVV - MBJ

EVVMBJ

Evansville Dress Regional

Tue 1/13

6:13 am-1:34 pm

1 stop6h 21m

Montego Bay Sangster Intl

Tue 2/3

12:33 pm-10:50 pm

1 stop11h 17m

$473

EvansvilleSaint Thomas Island

EVV - STT

EVVSTT

Evansville Dress Regional

Wed 5/20

5:34 am-2:28 pm

1 stop7h 54m

Saint Thomas Island Cyril E King

Tue 5/26

5:15 pm-9:56 am

2 stops17h 41m

$544

EvansvillePunta Cana

EVV - PUJ

EVVPUJ

Evansville Dress Regional

Sat 12/27

4:51 pm-4:42 pm

1 stop21h 51m

Punta Cana

Thu 1/1

2:27 pm-11:48 pm

1 stop11h 21m

$713

EvansvilleMontego Bay

EVV - MBJ

EVVMBJ

Evansville Dress Regional

Sun 1/25

11:40 am-6:24 pm

2 stops29h 44m

Montego Bay Sangster Intl

Thu 1/29

2:55 pm-5:19 pm

2 stops27h 24m

$1,726

EvansvilleSan Juan

EVV - SJU

EVVSJU

Evansville Dress Regional

Mon 12/22

12:22 pm-1:39 am

2 stops35h 17m

$197

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/10

Showing 1-10 of 16 results
1
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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, March is the cheapest month in which you can book a flight from Evansville to Caribbean (average of $190). Flying from Evansville to Caribbean in June is currently the most expensive (average of $285). 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.

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 December 12, 2025.
Peruse reviews from past customers who have flown with Delta and American Airlines from Evansville to Caribbean to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
8,007 reviews

Food

7.3

Comfort

7.9

Crew

8.5

Boarding

8.1

Entertainment

7.9

Overall

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Delta
7.9
Good
8,007 reviews
Delta
7.9
Good
8,007 reviews

Food

7.3

Comfort

7.9

Crew

8.5

Boarding

8.1

Entertainment

7.9

Overall

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
American Airlines
7.2
Good
11,050 reviews
Delta
7.9
Good
8,007 reviews

Food

7.3

Comfort

7.9

Crew

8.5

Boarding

8.1

Entertainment

7.9

Overall

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

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.

  • How long is the flight from Evansville to Caribbean?

    There are many flights that can get you from Evansville to Caribbean in 14h 47m. Fly via American Airlines to get the fastest option. There are 1874 mi between Evansville and Caribbean.

  • 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 - Punta Cana or Evansville Dress Regional - Montego Bay Sangster 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, March is the cheapest month in which you can book a flight from Evansville to Caribbean (average of $190). Flying from Evansville to Caribbean in June is currently the most expensive (average of $285). 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 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 December 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$275Average$583FlexibilityNo cancel feeOn-time71%
DeltaCheapest$371Average$556FlexibilityNo cancel feeOn-timeN/A

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