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$256+ Cheap flights from Evansville (EVV) to Caribbean

This is the cheapest round-trip 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.
EVV — SJU
Feb 26 — Mar 51
Thu 2/26
Thu 3/5
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 January 27, 2026.

This Delta deal was found by Cheapflights users on 1/25. 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.
Wed 2/1811:14 am
EVV
-
SJU
1 stop10h 44m
Delta
Tue 2/246:15 am
SJU
-
EVV
1 stop6h 18m
Delta
Deal found 1/25$256
This Kiwi.com deal was found by Cheapflights users on 1/25. 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 2/167:46 pm
EVV
-
SJU
1 stop12h 31m
Multiple Airlines
Thu 2/193:53 am
SJU
-
EVV
1 stop17h 13m
Multiple Airlines
Deal found 1/25$277
This Kiwi.com deal was found by Cheapflights users on 1/25. 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 3/27:46 pm
EVV
-
SJU
1 stop12h 08m
Multiple Airlines
Fri 3/66:30 am
SJU
-
EVV
1 stop14h 36m
Multiple Airlines
Deal found 1/25$304
This Kiwi.com deal was found by Cheapflights users on 1/25. 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.
Fri 2/137:46 pm
EVV
-
SJU
1 stop12h 31m
Multiple Airlines
Thu 2/193:53 am
SJU
-
EVV
1 stop17h 13m
Multiple Airlines
Deal found 1/25$305
This Kiwi.com deal was found by Cheapflights users on 1/25. 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.
Fri 2/277:46 pm
EVV
-
SJU
2 stops27h 38m
Multiple Airlines
Fri 3/611:04 am
SJU
-
EVV
1 stop10h 02m
Multiple Airlines
Deal found 1/25$315
This Kiwi.com deal was found by Cheapflights users on 1/25. 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 3/97:46 pm
EVV
-
SJU
1 stop12h 31m
Multiple Airlines
Thu 3/125:30 am
SJU
-
EVV
1 stop26h 49m
Multiple Airlines
Deal found 1/25$320
This American Airlines deal was found by Cheapflights users on 1/25. 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.
Sun 2/155:10 am
EVV
-
SJU
2 stops16h 30m
American Airlines
Wed 2/257:00 am
SJU
-
EVV
2 stops18h 28m
American Airlines
Deal found 1/25$324
This Kiwi.com deal was found by Cheapflights users on 1/25. 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 3/97:46 pm
EVV
-
SJU
1 stop12h 31m
Multiple Airlines
Thu 3/121:45 am
SJU
-
EVV
1 stop18h 21m
Multiple Airlines
Deal found 1/25$328
This Kiwi.com deal was found by Cheapflights users on 1/25. 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 3/97:46 pm
EVV
-
SJU
1 stop12h 31m
Multiple Airlines
Sun 3/157:54 pm
SJU
-
EVV
2 stops24h 12m
Multiple Airlines
Deal found 1/25$330
This American Airlines deal was found by Cheapflights users on 1/26. 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.
Tue 3/177:07 am
EVV
-
SJU
2 stops14h 51m
American Airlines
Tue 3/245:28 am
SJU
-
EVV
1 stop11h 21m
American Airlines
Deal found 1/26$335
This American Airlines deal was found by Cheapflights users on 1/25. 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 2/164:22 pm
EVV
-
SJU
1 stop11h 02m
American Airlines
Tue 2/248:00 am
SJU
-
EVV
2 stops16h 53m
American Airlines
Deal found 1/25$349
This American Airlines deal was found by Cheapflights users on 1/27. 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 3/186:57 pm
EVV
-
PUJ
2 stops18h 57m
American Airlines
Wed 3/2512:00 pm
PUJ
-
EVV
2 stops12h 46m
American Airlines
Deal found 1/27$462

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 January 27, 2026.

Round-trip from

$256
(Delta)

Popular in

December

Cheapest in

October

Average price

$490
From Evansville Dress Regional to Caribbean
Search Deals
Highest demand for flights based on searches. 24% potential increase in price ($179 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 16% potential price decrease ($77 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

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 January 27, 2026.
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

Wed 2/18

11:14 am-11:58 pm

1 stop10h 44m

San Juan Luis Munoz Marin Intl

Wed 2/25

6:15 am-10:33 am

1 stop6h 18m

$256

EvansvilleSan Juan

EVV - SJU

EVVSJU

Evansville Dress Regional

Wed 2/18

11:14 am-11:58 pm

1 stop10h 44m

San Juan Luis Munoz Marin Intl

Tue 2/24

6:15 am-10:33 am

1 stop6h 18m

$256

EvansvilleSan Juan

EVV - SJU

EVVSJU

Evansville Dress Regional

Sun 3/1

3:50 pm-4:20 pm

2 stops22h 30m

San Juan Luis Munoz Marin Intl

Thu 3/5

6:33 am-3:49 pm

1 stop11h 16m

$324

EvansvilleSan Juan

EVV - SJU

EVVSJU

Evansville Dress Regional

Mon 3/2

4:22 pm-5:24 am

1 stop11h 02m

San Juan Luis Munoz Marin Intl

Thu 3/5

6:33 am-3:49 pm

1 stop11h 16m

$324

EvansvilleSan Juan

EVV - SJU

EVVSJU

Evansville Dress Regional

Wed 2/18

11:14 am-11:58 pm

1 stop10h 44m

San Juan Luis Munoz Marin Intl

Fri 2/20

6:15 am-10:33 am

1 stop6h 18m

$332

EvansvilleSan Juan

EVV - SJU

EVVSJU

Evansville Dress Regional

Tue 3/17

7:07 am-10:58 pm

2 stops14h 51m

San Juan Luis Munoz Marin Intl

Tue 3/24

5:28 am-3:49 pm

1 stop11h 21m

$335

EvansvilleSan Juan

EVV - SJU

EVVSJU

Evansville Dress Regional

Mon 2/16

4:22 pm-5:24 am

1 stop11h 02m

San Juan Luis Munoz Marin Intl

Wed 2/25

7:00 am-10:53 pm

2 stops17h 53m

$349

EvansvilleSan Juan

EVV - SJU

EVVSJU

Evansville Dress Regional

Mon 3/2

6:57 pm-4:28 pm

2 stops19h 31m

San Juan Luis Munoz Marin Intl

Fri 3/6

6:33 am-3:49 pm

1 stop11h 16m

$379

EvansvillePunta Cana

EVV - PUJ

EVVPUJ

Evansville Dress Regional

Wed 3/18

6:57 pm-2:54 pm

2 stops18h 57m

Punta Cana

Wed 3/25

11:35 am-6:32 pm

1 stop7h 57m

$462

EvansvilleSaint Thomas Island

EVV - STT

EVVSTT

Evansville Dress Regional

Wed 4/8

4:13 pm-11:35 am

2 stops18h 22m

Saint Thomas Island Cyril E King

Wed 4/15

12:36 pm-11:55 pm

2 stops12h 19m

$468

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/25

Showing 1-10 of 20 results
1
2

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 January 27, 2026.
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
8,118 reviews

Crew

8.5

Comfort

7.9

Food

7.2

Overall

7.9

Boarding

8.1

Entertainment

7.8

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
8,118 reviews
Delta
7.9
Good
8,118 reviews

Crew

8.5

Comfort

7.9

Food

7.2

Overall

7.9

Boarding

8.1

Entertainment

7.8

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
11,197 reviews
Delta
7.9
Good
8,118 reviews

Crew

8.5

Comfort

7.9

Food

7.2

Overall

7.9

Boarding

8.1

Entertainment

7.8

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 10h 44m. Fly via Delta or American Airlines to get the fastest option. There are 1874 mi between Evansville and Caribbean. This flight may include one or multiple stops.

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

    Most travelers choose Evansville Dress Regional - Saint Thomas Island Cyril E King, Evansville Dress Regional - San Juan Luis Munoz Marin 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, 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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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 January 27, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$275Average$574FlexibilityNo cancel feeOn-time71%
DeltaCheapest$371Average$560FlexibilityNo cancel feeOn-timeN/A

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