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Caribbean Islands

$248+ Cheap flights from Evansville (EVV) to Caribbean Islands

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 12/13. Fares are subject to change and may not be available on all flights or dates of travel.
EVV — SJU
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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Cheap 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 September 11, 2025.

Round-trip from

$325
(American Airlines)

One-way from

$248
(American Airlines)

Popular in

January

Cheapest in

February
From Evansville Dress Regional to Caribbean Islands
Search Deals
One-way flight from Evansville Dress Regional to Caribbean Islands
Search Deals
Highest demand for flights based on searches. 9% potential increase in price ($55 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($28 potential savings vs. average RT price).
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Find 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 September 11, 2025.

This American Airlines deal was found by Cheapflights users on 9/10. 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 10/251:41 pmEVV - PUJ
2 stops20h 54mAmerican Airlines
Sat 11/14:45 pmPUJ - EVV
2 stops19h 22mAmerican Airlines
Deal found 9/10$382
This American Airlines deal was found by Cheapflights users on 9/11. 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.
Sun 10/267:00 amEVV - MBJ
1 stop7h 15mAmerican Airlines
Sun 11/22:04 pmMBJ - EVV
1 stop10h 45mAmerican Airlines
Deal found 9/11$569
This American Airlines deal was found by Cheapflights users on 9/11. 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.
Thu 11/275:10 amEVV - SJU
2 stops28h 02mAmerican Airlines
Sun 11/301:59 amSJU - EVV
2 stops10h 37mAmerican Airlines
Deal found 9/11$592
This American Airlines deal was found by Cheapflights users on 9/11. 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.
Sun 12/76:03 pmEVV - STT
2 stops19h 22mAmerican Airlines
Sat 12/134:22 pmSTT - EVV
2 stops19h 39mAmerican Airlines
Deal found 9/11$594
This American Airlines deal was found by Cheapflights users on 9/9. 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.
Thu 11/207:10 pmEVV - MBJ
2 stops18h 40mAmerican Airlines
Sun 11/232:14 pmMBJ - EVV
1 stop10h 35mAmerican Airlines
Deal found 9/9$598
This American Airlines deal was found by Cheapflights users on 9/10. 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 11/811:03 amEVV - SJU
2 stops10h 49mAmerican Airlines
Sun 11/168:00 amSJU - EVV
1 stop17h 59mAmerican Airlines
Deal found 9/10$630
This American Airlines deal was found by Cheapflights users on 9/9. 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.
Fri 9/125:59 pmEVV - SJU
2 stops19h 54mAmerican Airlines
Sun 9/146:10 amSJU - EVV
2 stops18h 19mAmerican Airlines
Deal found 9/9$672
This American Airlines deal was found by Cheapflights users on 9/9. 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.
Fri 9/126:04 pmEVV - SJU
2 stops17h 46mAmerican Airlines
Sat 9/133:05 pmSJU - EVV
2 stops31h 14mAmerican Airlines
Deal found 9/9$689
This American Airlines deal was found by Cheapflights users on 9/10. 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 12/187:05 amEVV - SJU
2 stops12h 23mAmerican Airlines
Mon 12/226:05 amSJU - EVV
1 stop12h 16mAmerican Airlines
Deal found 9/10$705
This Kiwi.com deal was found by Cheapflights users on 9/9. 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.
Fri 9/1212:22 pmEVV - SJU
1 stop11h 32mMultiple Airlines
Sun 9/143:39 amSJU - EVV
1 stop9h 03mMultiple Airlines
Deal found 9/9$744
This Kiwi.com deal was found by Cheapflights users on 9/9. 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.
Fri 9/1212:22 pmEVV - SJU
2 stops22h 39mMultiple Airlines
Sun 9/149:07 amSJU - EVV
1 stop27h 35mMultiple Airlines
Deal found 9/9$769
This Delta deal was found by Cheapflights users on 9/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/76:00 amEVV - STT
1 stop6h 43mDelta
Sat 12/133:50 pmSTT - EVV
1 stop8h 16mDelta
Deal found 9/11$1,009

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 September 11, 2025.
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

Mon 12/1

7:05 pm-1:38 pm

2 stops16h 33m

San Juan Luis Munoz Marin Intl

Sat 12/6

8:18 am-9:15 pm

2 stops14h 57m

$325

EvansvilleSan Juan

EVV - SJU

EVVSJU

Evansville Dress Regional

Mon 3/9

2:35 pm-12:35 pm

2 stops21h 00m

San Juan Luis Munoz Marin Intl

Fri 3/13

4:40 am-9:11 pm

2 stops17h 31m

$364

EvansvillePunta Cana

EVV - PUJ

EVVPUJ

Evansville Dress Regional

Sat 10/25

1:41 pm-11:35 am

2 stops20h 54m

Punta Cana

Sat 11/1

4:45 pm-11:07 am

2 stops19h 22m

$382

EvansvilleSanto Domingo

EVV - SDQ

EVVSDQ

Evansville Dress Regional

Thu 3/5

5:45 pm-1:30 pm

2 stops17h 45m

Santo Domingo Las Americas

Mon 3/9

7:05 am-9:26 am

2 stops27h 21m

$507

EvansvilleMontego Bay

EVV - MBJ

EVVMBJ

Evansville Dress Regional

Sun 3/8

5:45 pm-10:10 am

1 stop16h 25m

Montego Bay Sangster Intl

Wed 3/11

8:00 am-4:56 pm

1 stop8h 56m

$531

EvansvilleMontego Bay

EVV - MBJ

EVVMBJ

Evansville Dress Regional

Tue 1/13

6:45 am-2:44 pm

1 stop6h 59m

Montego Bay Sangster Intl

Tue 2/3

11:50 am-9:13 pm

1 stop10h 23m

$539

EvansvilleMontego Bay

EVV - MBJ

EVVMBJ

Evansville Dress Regional

Sun 10/26

7:00 am-2:15 pm

1 stop7h 15m

Montego Bay Sangster Intl

Sun 11/2

2:04 pm-11:49 pm

1 stop10h 45m

$569

EvansvilleSan Juan

EVV - SJU

EVVSJU

Evansville Dress Regional

Thu 11/27

5:10 am-10:10 am

2 stops27h 00m

San Juan Luis Munoz Marin Intl

Mon 12/1

3:53 pm-11:49 pm

1 stop9h 56m

$592

EvansvilleSaint Thomas Island

EVV - STT

EVVSTT

Evansville Dress Regional

Sun 12/7

6:03 pm-3:25 pm

2 stops19h 22m

Saint Thomas Island Cyril E King

Sat 12/13

4:22 pm-10:01 am

2 stops19h 39m

$594

EvansvilleSan Juan

EVV - SJU

EVVSJU

Evansville Dress Regional

Sat 11/8

5:10 am-9:24 pm

1 stop14h 14m

San Juan Luis Munoz Marin Intl

Sun 11/16

4:44 pm-11:59 pm

1 stop9h 15m

$630

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/10

Showing 1-10 of 12 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, September is the cheapest month in which you can book a flight from Evansville to Caribbean Islands (average of $254). Flying from Evansville to Caribbean Islands 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.

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 September 11, 2025.
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
8.0
Very good
7,960 reviews

Entertainment

7.9

Crew

8.5

Boarding

8.2

Comfort

7.9

Overall

8.0

Food

7.3

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
7,960 reviews
Delta
8.0
Very good
7,960 reviews

Entertainment

7.9

Crew

8.5

Boarding

8.2

Comfort

7.9

Overall

8.0

Food

7.3

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
7,960 reviews

Entertainment

7.9

Crew

8.5

Boarding

8.2

Comfort

7.9

Overall

8.0

Food

7.3

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 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 $325, American Airlines can have you in Caribbean Islands from Evansville in 16h 33m. 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 - San Juan Luis Munoz Marin Intl, Evansville Dress Regional - Punta Cana and Evansville Dress Regional - Montego Bay Sangster Intl.

  • 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, September is the cheapest month in which you can book a flight from Evansville to Caribbean Islands (average of $254). Flying from Evansville to Caribbean Islands 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 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 September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$292Average$605FlexibilityNo cancel feeOn-time71%
DeltaCheapest$371Average$556FlexibilityNo cancel feeOn-timeN/A

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