HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Caribbean Islands

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

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
jue. 2/26
jue. 3/5
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Evansville to Caribbean Islands with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Evansville to Caribbean Islands

Cheapest flights from Evansville to Caribbean Islands
Explore the most affordable flight options available from Evansville to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on enero 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.
mié. 2/1811:14 am
EVV
-
SJU
1 stop10h 44m
Delta
mar. 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.
lun. 2/167:46 pm
EVV
-
SJU
1 stop12h 31m
Multiple Airlines
jue. 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.
lun. 3/27:46 pm
EVV
-
SJU
1 stop12h 08m
Multiple Airlines
vie. 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.
vie. 2/137:46 pm
EVV
-
SJU
1 stop12h 31m
Multiple Airlines
jue. 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.
vie. 2/277:46 pm
EVV
-
SJU
2 stops27h 38m
Multiple Airlines
vie. 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.
lun. 3/97:46 pm
EVV
-
SJU
1 stop12h 31m
Multiple Airlines
jue. 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.
dom. 2/155:10 am
EVV
-
SJU
2 stops16h 30m
American Airlines
mié. 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.
lun. 3/97:46 pm
EVV
-
SJU
1 stop12h 31m
Multiple Airlines
jue. 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.
lun. 3/97:46 pm
EVV
-
SJU
1 stop12h 31m
Multiple Airlines
dom. 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.
mar. 3/177:07 am
EVV
-
SJU
2 stops14h 51m
American Airlines
mar. 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.
lun. 2/164:22 pm
EVV
-
SJU
1 stop11h 02m
American Airlines
mar. 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.
mié. 3/186:57 pm
EVV
-
PUJ
2 stops18h 57m
American Airlines
mié. 3/2512:00 pm
PUJ
-
EVV
2 stops12h 46m
American Airlines
Deal found 1/27$462

Find flight deals from Evansville to Caribbean Islands

Keep the following information in mind while searching for Evansville to Caribbean Islands flight deals. Data was last updated enero 27, 2026.

Round-trip from

$256
(Delta)

Popular in

December

Cheapest in

October

Average price

$490
From Evansville Dress Regional to Caribbean Islands
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 Islands 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 enero 27, 2026.
Use the filters below to find and compare flights from Evansville to Caribbean Islands that are best for you.

Fly from

Evansville

Fly to

Caribbean Islands

Route

Depart

Return

Price

EvansvilleSan Juan

EVV - SJU

EVVSJU

Evansville Dress Regional

mié. 2/18

11:14 am-11:58 pm

1 stop10h 44m

San Juan Luis Munoz Marin Intl

mié. 2/25

6:15 am-10:33 am

1 stop6h 18m

$256

EvansvilleSan Juan

EVV - SJU

EVVSJU

Evansville Dress Regional

mié. 2/18

11:14 am-11:58 pm

1 stop10h 44m

San Juan Luis Munoz Marin Intl

mar. 2/24

6:15 am-10:33 am

1 stop6h 18m

$256

EvansvilleSan Juan

EVV - SJU

EVVSJU

Evansville Dress Regional

dom. 3/1

3:50 pm-4:20 pm

2 stops22h 30m

San Juan Luis Munoz Marin Intl

jue. 3/5

6:33 am-3:49 pm

1 stop11h 16m

$324

EvansvilleSan Juan

EVV - SJU

EVVSJU

Evansville Dress Regional

lun. 3/2

4:22 pm-5:24 am

1 stop11h 02m

San Juan Luis Munoz Marin Intl

jue. 3/5

6:33 am-3:49 pm

1 stop11h 16m

$324

EvansvilleSan Juan

EVV - SJU

EVVSJU

Evansville Dress Regional

mié. 2/18

11:14 am-11:58 pm

1 stop10h 44m

San Juan Luis Munoz Marin Intl

vie. 2/20

6:15 am-10:33 am

1 stop6h 18m

$332

EvansvilleSan Juan

EVV - SJU

EVVSJU

Evansville Dress Regional

mar. 3/17

7:07 am-10:58 pm

2 stops14h 51m

San Juan Luis Munoz Marin Intl

mar. 3/24

5:28 am-3:49 pm

1 stop11h 21m

$335

EvansvilleSan Juan

EVV - SJU

EVVSJU

Evansville Dress Regional

lun. 2/16

4:22 pm-5:24 am

1 stop11h 02m

San Juan Luis Munoz Marin Intl

mié. 2/25

7:00 am-10:53 pm

2 stops17h 53m

$349

EvansvilleSan Juan

EVV - SJU

EVVSJU

Evansville Dress Regional

lun. 3/2

6:57 pm-4:28 pm

2 stops19h 31m

San Juan Luis Munoz Marin Intl

vie. 3/6

6:33 am-3:49 pm

1 stop11h 16m

$379

EvansvillePunta Cana

EVV - PUJ

EVVPUJ

Evansville Dress Regional

mié. 3/18

6:57 pm-2:54 pm

2 stops18h 57m

Punta Cana

mié. 3/25

11:35 am-6:32 pm

1 stop7h 57m

$462

EvansvilleSaint Thomas Island

EVV - STT

EVVSTT

Evansville Dress Regional

mié. 4/8

4:13 pm-11:35 am

2 stops18h 22m

Saint Thomas Island Cyril E King

mié. 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 Islands

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

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

Currently, March is the cheapest month in which you can book a flight from Evansville to Caribbean Islands (average of $190). Flying from Evansville to Caribbean Islands 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 Islands

Get insights into the airlines that provide service to Caribbean Islands. 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 Islands. Reviews last updated enero 27, 2026.
Get a feel of what it's like to fly with Delta and American Airlines from Evansville to Caribbean Islands by reading reviews from past customers. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
8,118 reviews

Food

7.2

Boarding

8.1

Overall

7.9

Comfort

7.9

Crew

8.5

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

Food

7.2

Boarding

8.1

Overall

7.9

Comfort

7.9

Crew

8.5

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

Food

7.2

Boarding

8.1

Overall

7.9

Comfort

7.9

Crew

8.5

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 Islands. 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 Islands?

    Evansville Dress Regional (EVV) is the airport you will fly out of if you book a flight from Evansville to Caribbean Islands. It is only a 4.4 mi journey to Dress Regional (EVV) from Evansville’s city center.

  • How long is the flight from Evansville to Caribbean Islands?

    For as low as $256, Delta can have you in Caribbean Islands from Evansville in 10h 44m. The distance between Evansville and Caribbean Islands is about 1874 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

    The most popular flight routes from Evansville to Caribbean Islands are Evansville Dress Regional - Saint Thomas Island Cyril E King, Evansville Dress Regional - San Juan Luis Munoz Marin Intl and Evansville Dress Regional - Punta Cana.

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

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

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

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

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

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

    Currently, March is the cheapest month in which you can book a flight from Evansville to Caribbean Islands (average of $190). Flying from Evansville to Caribbean Islands 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Evansville to Caribbean Islands

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Cancún flights
O'Hare Intl to Sky Harbor Intl flights
O'Hare Intl to Las Vegas flights
O'Hare Intl to Dallas/Fort Worth flights
O'Hare Intl to Los Angeles flights
O'Hare Intl to Mexico City flights
O'Hare Intl to Fort Lauderdale flights
O'Hare Intl to John F Kennedy Intl flights
O'Hare Intl to Miami flights
O'Hare Intl to Orlando flights
O'Hare Intl to Denver flights
O'Hare Intl to San Francisco flights
O'Hare Intl to Seattle flights
O'Hare Intl to Tampa flights
O'Hare Intl to LaGuardia flights
Cincinnati to Orlando flights
O'Hare Intl to Fort Myers flights
O'Hare Intl to Newark flights
Midway to Fort Lauderdale flights
Midway to Sky Harbor Intl flights
Midway to Cancún flights
O'Hare Intl to Atlanta flights
Cincinnati to Las Vegas flights
O'Hare Intl to West Palm Beach flights
Cincinnati to Tampa flights
Midway to Miami flights
O'Hare Intl to Cozumel flights
Midway to Dallas/Fort Worth flights
Midway to Las Vegas flights
O'Hare Intl to New Orleans flights
O'Hare Intl to Honolulu flights
O'Hare Intl to Santa Ana flights
O'Hare Intl to San Diego flights
O'Hare Intl to Sarasota flights
O'Hare Intl to Boston flights
O'Hare Intl to Reagan-National flights
Cincinnati to Fort Myers flights
Cincinnati to Fort Lauderdale flights
Midway to Orlando flights
O'Hare Intl to Ontario flights
Midway to Newark flights
Indianapolis to Orlando flights
O'Hare Intl to George Bush Intcntl flights
O'Hare Intl to Palm Springs flights
Midway to Mexico City flights
O'Hare Intl to Charleston flights
O'Hare Intl to Hobby flights
Cincinnati to LaGuardia flights
O'Hare Intl to Dulles Intl flights
Indianapolis to Las Vegas flights

Top 2 airlines flying from Evansville to Caribbean Islands

Discover the top 2 airlines that operate flights from Evansville to Caribbean Islands. 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 enero 27, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$275Average$574FlexibilityNo cancel feeOn-time71%
DeltaCheapest$371Average$560FlexibilityNo cancel feeOn-timeN/A

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.