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Caribbean Islands

$325+ 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
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
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 October 30, 2025.

Round-trip from

$368
(American Airlines)

Popular in

January

Cheapest in

October

Average price

$285
From Evansville Dress Regional to Caribbean Islands
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($61 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($23 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
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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 October 30, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/30. 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 12/85:35 pmEVV - PUJ
1 stop22h 25mMultiple Airlines
Sat 12/136:08 pmPUJ - EVV
2 stops22h 29mMultiple Airlines
Deal found 10/30$427
This American Airlines deal was found by Cheapflights users on 10/30. 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 12/86:45 amEVV - PUJ
1 stop6h 22mAmerican Airlines
Sat 12/1312:51 pmPUJ - EVV
1 stop13h 07mAmerican Airlines
Deal found 10/30$456
This Kiwi.com deal was found by Cheapflights users on 10/29. 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.
Sun 12/143:27 pmEVV - STT
1 stop21h 22mMultiple Airlines
Sun 12/283:23 pmSTT - EVV
1 stop22h 19mMultiple Airlines
Deal found 10/29$477
This Kiwi.com deal was found by Cheapflights users on 10/28. 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.
Sun 12/212:52 pmEVV - SJU
1 stop23h 07mMultiple Airlines
Sun 12/2810:08 amSJU - EVV
1 stop27h 34mMultiple Airlines
Deal found 10/28$514
This American Airlines deal was found by Cheapflights users on 10/28. 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 12/127:00 amEVV - MBJ
1 stop7h 22mAmerican Airlines
Fri 12/192:34 pmMBJ - EVV
1 stop10h 03mAmerican Airlines
Deal found 10/28$564
This American Airlines deal was found by Cheapflights users on 10/29. 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
Mon 12/17:15 amSJU - EVV
1 stop17h 49mAmerican Airlines
Deal found 10/29$590
This American Airlines deal was found by Cheapflights users on 10/30. 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
1 stop8h 21mAmerican Airlines
Sun 11/167:15 amSJU - EVV
1 stop18h 28mAmerican Airlines
Deal found 10/30$662
This American Airlines deal was found by Cheapflights users on 10/30. 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 12/185:22 pmEVV - SJU
2 stops14h 13mAmerican Airlines
Mon 12/226:00 amSJU - EVV
1 stop12h 52mAmerican Airlines
Deal found 10/30$670
This American Airlines deal was found by Cheapflights users on 10/29. 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 12/143:50 pmEVV - STT
2 stops23h 08mAmerican Airlines
Sun 12/281:30 pmSTT - EVV
2 stops11h 54mAmerican Airlines
Deal found 10/29$693
This American Airlines deal was found by Cheapflights users on 10/28. 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 11/106:43 amEVV - MBJ
1 stop7h 07mAmerican Airlines
Mon 11/243:13 pmMBJ - EVV
1 stop9h 41mAmerican Airlines
Deal found 10/28$699
This American Airlines deal was found by Cheapflights users on 10/29. 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 12/273:47 pmEVV - PUJ
1 stop17h 41mAmerican Airlines
Thu 1/15:39 pmPUJ - EVV
2 stops19h 02mAmerican Airlines
Deal found 10/29$828

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 October 30, 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

Wed 2/18

6:07 pm-11:55 am

2 stops15h 48m

San Juan Luis Munoz Marin Intl

Mon 3/2

6:30 am-3:47 pm

1 stop11h 17m

$325

EvansvilleSan Juan

EVV - SJU

EVVSJU

Evansville Dress Regional

Mon 3/9

4:56 pm-1:33 pm

2 stops19h 37m

San Juan Luis Munoz Marin Intl

Fri 3/13

4:40 am-9:11 pm

2 stops17h 31m

$368

EvansvilleSan Juan

EVV - SJU

EVVSJU

Evansville Dress Regional

Sat 1/17

6:13 am-6:22 pm

2 stops10h 09m

San Juan Luis Munoz Marin Intl

Mon 1/26

5:55 pm-10:50 pm

1 stop6h 55m

$412

EvansvillePunta Cana

EVV - PUJ

EVVPUJ

Evansville Dress Regional

Mon 12/8

5:35 pm-6:00 pm

1 stop22h 25m

Punta Cana

Sat 12/13

6:08 pm-2:37 pm

2 stops22h 29m

$427

EvansvillePunta Cana

EVV - PUJ

EVVPUJ

Evansville Dress Regional

Mon 12/8

6:45 am-3:07 pm

1 stop6h 22m

Punta Cana

Sat 12/13

12:51 pm-11:58 pm

1 stop13h 07m

$456

EvansvillePunta Cana

EVV - PUJ

EVVPUJ

Evansville Dress Regional

Tue 4/21

4:53 pm-12:40 pm

2 stops18h 47m

Punta Cana

Sat 4/25

4:45 pm-9:56 am

2 stops18h 11m

$460

EvansvilleSaint Thomas Island

EVV - STT

EVVSTT

Evansville Dress Regional

Sun 12/14

3:27 pm-2:49 pm

1 stop21h 22m

Saint Thomas Island Cyril E King

Sun 12/28

3:23 pm-11:42 am

1 stop22h 19m

$477

EvansvillePunta Cana

EVV - PUJ

EVVPUJ

Evansville Dress Regional

Mon 2/23

5:45 pm-3:53 pm

2 stops20h 08m

Punta Cana

Fri 2/27

2:45 pm-11:26 am

2 stops22h 41m

$478

EvansvillePunta Cana

EVV - PUJ

EVVPUJ

Evansville Dress Regional

Sat 3/14

4:56 pm-12:40 pm

2 stops18h 44m

Punta Cana

Fri 3/20

3:40 pm-10:10 am

2 stops19h 30m

$496

EvansvilleMontego Bay

EVV - MBJ

EVVMBJ

Evansville Dress Regional

Sun 3/8

10:05 am-7:25 pm

1 stop9h 20m

Montego Bay Sangster Intl

Wed 3/11

8:00 am-10:05 pm

1 stop14h 05m

$531

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/30

Showing 1-10 of 17 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, January is the cheapest month in which you can book a flight from Evansville to Caribbean Islands (average of $167). Flying from Evansville to Caribbean Islands in August is currently the most expensive (average of $287). 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 October 30, 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
7.9
Good
7,998 reviews

Overall

7.9

Boarding

8.2

Entertainment

7.9

Crew

8.5

Comfort

7.9

Food

7.3

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
Delta
7.9
Good
7,998 reviews
Delta
7.9
Good
7,998 reviews

Overall

7.9

Boarding

8.2

Entertainment

7.9

Crew

8.5

Comfort

7.9

Food

7.3

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
American Airlines
7.2
Good
11,035 reviews
Delta
7.9
Good
7,998 reviews

Overall

7.9

Boarding

8.2

Entertainment

7.9

Crew

8.5

Comfort

7.9

Food

7.3

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.

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 15h 48m. 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 - Montego Bay Sangster 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, January is the cheapest month in which you can book a flight from Evansville to Caribbean Islands (average of $167). Flying from Evansville to Caribbean Islands in August is currently the most expensive (average of $287). 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 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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$275Average$587FlexibilityNo cancel feeOn-time71%
DeltaCheapest$371Average$556FlexibilityNo cancel feeOn-timeN/A

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