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Caribbean Islands

$373+ 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 12/9. Fares are subject to change and may not be available on all flights or dates of travel.
EVV — SJU
Jul 1 — Jul 81
Tue 7/1
Tue 7/8
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 June 26, 2025.

Round-trip from

$373
(American Airlines)

Popular in

August

Cheapest in

September

Average price

$523
From Evansville Dress Regional to Caribbean Islands
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($49 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($27 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 2025
Search Deals

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 June 26, 2025.

This American Airlines deal was found by Cheapflights users on 6/26. 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 12/95:52 amEVV - SJU
2 stops12h 53mAmerican Airlines
Mon 12/227:20 amSJU - EVV
1 stop16h 36mAmerican Airlines
Deal found 6/26$373
This American Airlines deal was found by Cheapflights users on 6/26. 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.
Sat 7/264:31 pmEVV - PUJ
2 stops19h 04mAmerican Airlines
Sat 8/24:10 pmPUJ - EVV
2 stops19h 25mAmerican Airlines
Deal found 6/26$380
This American Airlines deal was found by Cheapflights users on 6/25. 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.
Sat 8/3011:03 amEVV - STT
2 stops22h 57mAmerican Airlines
Fri 9/55:10 pmSTT - EVV
2 stops20h 51mAmerican Airlines
Deal found 6/25$509
This Delta deal was found by Cheapflights users on 6/25. 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.
Sat 8/306:10 amEVV - STT
1 stop8h 00mDelta
Fri 9/53:23 pmSTT - EVV
1 stop7h 31mDelta
Deal found 6/25$625
This American Airlines deal was found by Cheapflights users on 6/25. 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 7/205:48 pmEVV - MBJ
2 stops18h 17mAmerican Airlines
Sun 7/272:25 pmMBJ - EVV
2 stops20h 10mAmerican Airlines
Deal found 6/25$636
This American Airlines deal was found by Cheapflights users on 6/23. 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 12/76:47 amEVV - SKB
2 stops29h 28mAmerican Airlines
Thu 12/113:30 pmSKB - EVV
2 stops20h 37mAmerican Airlines
Deal found 6/23$736
This Mytrip deal was found by Cheapflights users on 6/25. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/202:13 pmEVV - MBJ
3 stops20h 52mMultiple Airlines
Sun 7/2710:48 amMBJ - EVV
3 stops29h 01mMultiple Airlines
Deal found 6/25$839
This WestJet deal was found by Cheapflights users on 6/25. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/99:37 amEVV - MBJ
2 stops26h 56mWestJet
Sat 8/1610:30 amMBJ - EVV
2 stops30h 40mWestJet
Deal found 6/25$3,431
This Delta deal was found by Cheapflights users on 6/26. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/96:00 amEVV - SJU
1 stop9h 15mDelta
Sun 12/213:13 amSJU - EVV
2 stops13h 48mDelta
Deal found 6/26$3,517

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 June 26, 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

Tue 12/9

5:52 am-8:45 pm

2 stops12h 53m

San Juan Luis Munoz Marin Intl

Mon 12/22

7:20 am-9:56 pm

1 stop16h 36m

$373

EvansvillePunta Cana

EVV - PUJ

EVVPUJ

Evansville Dress Regional

Sat 7/26

4:31 pm-12:35 pm

2 stops19h 04m

Punta Cana

Sat 8/2

4:10 pm-10:35 am

2 stops19h 25m

$380

EvansvilleSaint Thomas Island

EVV - STT

EVVSTT

Evansville Dress Regional

Sat 8/30

11:03 am-11:00 am

2 stops22h 57m

Saint Thomas Island Cyril E King

Fri 9/5

5:10 pm-1:01 pm

2 stops20h 51m

$509

EvansvilleSaint Thomas Island

EVV - STT

EVVSTT

Evansville Dress Regional

Sat 8/30

6:10 am-3:10 pm

1 stop8h 00m

Saint Thomas Island Cyril E King

Fri 9/5

3:23 pm-9:54 pm

1 stop7h 31m

$625

EvansvilleMontego Bay

EVV - MBJ

EVVMBJ

Evansville Dress Regional

Sun 7/20

5:05 am-3:25 pm

1 stop10h 20m

Montego Bay Sangster Intl

Sun 7/27

2:25 pm-10:35 am

2 stops20h 10m

$636

EvansvilleBasseterre

EVV - SKB

EVVSKB

Evansville Dress Regional

Sun 12/7

6:47 am-2:15 pm

2 stops29h 28m

Basseterre Robert Bradshaw Intl

Thu 12/11

3:30 pm-10:07 am

2 stops20h 37m

$736

EvansvilleMontego Bay

EVV - MBJ

EVVMBJ

Evansville Dress Regional

Sun 7/20

2:13 pm-11:05 am

3 stops20h 52m

Montego Bay Sangster Intl

Sun 7/27

10:48 am-3:49 pm

3 stops29h 01m

$839

EvansvilleMontego Bay

EVV - MBJ

EVVMBJ

Evansville Dress Regional

Sat 8/9

9:37 am-12:33 pm

2 stops26h 56m

Montego Bay Sangster Intl

Sat 8/16

10:30 am-5:10 pm

2 stops30h 40m

$3,431

EvansvilleSan Juan

EVV - SJU

EVVSJU

Evansville Dress Regional

Tue 12/9

6:00 am-5:15 pm

1 stop9h 15m

San Juan Luis Munoz Marin Intl

Sun 12/21

3:13 am-3:01 pm

2 stops13h 48m

$3,517

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/26

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 June 26, 2025.
Get a feel of what it's like to fly with Delta, American Airlines, and WestJet 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
7,964 reviews

Entertainment

7.9

Comfort

7.9

Crew

8.5

Food

7.3

Overall

8.0

Boarding

8.2

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
7,964 reviews
Delta
8.0
Very good
7,964 reviews

Entertainment

7.9

Comfort

7.9

Crew

8.5

Food

7.3

Overall

8.0

Boarding

8.2

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
7,964 reviews

Entertainment

7.9

Comfort

7.9

Crew

8.5

Food

7.3

Overall

8.0

Boarding

8.2

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!
WestJet
7.2
Good
2,893 reviews
Delta
8.0
Very good
7,964 reviews

Entertainment

7.9

Comfort

7.9

Crew

8.5

Food

7.3

Overall

8.0

Boarding

8.2

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.

  • 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, 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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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 June 26, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$284Average$631FlexibilityNo cancel feeOn-time71%
DeltaCheapest$371Average$622FlexibilityNo cancel feeOn-timeN/A

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