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$211+ Cheap flights from Evansville (EVV) to Caribbean

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 8/29. Fares are subject to change and may not be available on all flights or dates of travel.
EVV — SJU
Aug 3 — Aug 101
Sun 8/3
Sun 8/10
1 adult, Economy
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Cheap flight deals from Evansville to Caribbean

Keep the following information in mind while searching for Evansville to Caribbean flight deals. Data was last updated July 29, 2025.

Round-trip from

$271
(American Airlines)

One-way from

$211
(Kiwi.com)

Popular in

August

Cheapest in

February

Average price

$566
From Evansville Dress Regional to Caribbean
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One-way flight from Evansville Dress Regional to Caribbean
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Highest demand for flights based on searches. 20% potential increase in price ($143 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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Average for round-trip flights in July 2025
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Find 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 July 29, 2025.

This American Airlines deal was found by Cheapflights users on 7/28. 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 10/316:50 amEVV - SJU
2 stops16h 09mAmerican Airlines
Tue 11/42:41 pmSJU - EVV
2 stops10h 10mAmerican Airlines
Deal found 7/28$271
This American Airlines deal was found by Cheapflights users on 7/27. 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.
Thu 10/235:19 pmEVV - PUJ
2 stops20h 58mAmerican Airlines
Sun 10/2612:36 pmPUJ - EVV
2 stops23h 03mAmerican Airlines
Deal found 7/27$410
This American Airlines deal was found by Cheapflights users on 7/27. 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 9/101:56 pmEVV - MBJ
2 stops22h 09mAmerican Airlines
Wed 9/171:05 pmMBJ - EVV
1 stop8h 39mAmerican Airlines
Deal found 7/27$593
This American Airlines deal was found by Cheapflights users on 7/26. 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.
Sun 12/74:58 pmEVV - SKB
2 stops19h 17mAmerican Airlines
Thu 12/113:30 pmSKB - EVV
2 stops48h 51mAmerican Airlines
Deal found 7/26$779
This WestJet deal was found by Cheapflights users on 7/29. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/126:10 amEVV - PUJ
2 stops28h 18mWestJet
Tue 8/193:35 pmPUJ - EVV
2 stops42h 58mWestJet
Deal found 7/29$3,459
This Delta deal was found by Cheapflights users on 7/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/186:00 amEVV - SJU
1 stop9h 15mDelta
Sun 12/213:13 amSJU - EVV
2 stops13h 48mDelta
Deal found 7/28$3,617

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 July 29, 2025.
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

Fri 10/31

6:50 am-11:59 pm

2 stops16h 09m

San Juan Luis Munoz Marin Intl

Tue 11/4

2:41 pm-10:51 pm

2 stops10h 10m

$271

EvansvillePunta Cana

EVV - PUJ

EVVPUJ

Evansville Dress Regional

Thu 10/23

5:19 pm-3:17 pm

2 stops20h 58m

Punta Cana

Sun 10/26

12:36 pm-10:39 am

2 stops23h 03m

$410

EvansvilleMontego Bay

EVV - MBJ

EVVMBJ

Evansville Dress Regional

Wed 9/10

1:56 pm-12:05 pm

2 stops22h 09m

Montego Bay Sangster Intl

Wed 9/17

1:05 pm-9:44 pm

1 stop8h 39m

$593

EvansvilleBasseterre

EVV - SKB

EVVSKB

Evansville Dress Regional

Sun 12/7

4:58 pm-2:15 pm

2 stops19h 17m

Basseterre Robert Bradshaw Intl

Thu 12/11

3:30 pm-2:21 pm

2 stops48h 51m

$779

EvansvillePunta Cana

EVV - PUJ

EVVPUJ

Evansville Dress Regional

Tue 8/12

6:10 am-11:28 am

2 stops28h 18m

Punta Cana

Tue 8/19

3:35 pm-9:33 am

2 stops42h 58m

$3,459

EvansvilleSan Juan

EVV - SJU

EVVSJU

Evansville Dress Regional

Thu 12/18

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

$3,617

EvansvilleSanto Domingo

EVV - SDQ

EVVSDQ

Evansville Dress Regional

Fri 8/29

7:19 pm-11:56 am

1 stop15h 37m

$211

EvansvilleSanto Domingo

EVV - SDQ

EVVSDQ

Evansville Dress Regional

Sun 8/31

10:13 am-12:57 am

2 stops13h 44m

$281

EvansvilleSanto Domingo

EVV - SDQ

EVVSDQ

Evansville Dress Regional

Thu 8/28

5:36 pm-9:25 am

2 stops14h 49m

$316

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/26

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

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 July 29, 2025.
Peruse reviews from past customers who have flown with Delta, American Airlines, and WestJet 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
8.0
Very good
7,977 reviews

Boarding

8.2

Overall

8.0

Entertainment

7.9

Comfort

7.9

Crew

8.5

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
7,977 reviews
Delta
8.0
Very good
7,977 reviews

Boarding

8.2

Overall

8.0

Entertainment

7.9

Comfort

7.9

Crew

8.5

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
7,977 reviews

Boarding

8.2

Overall

8.0

Entertainment

7.9

Comfort

7.9

Crew

8.5

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!
WestJet
7.2
Good
2,973 reviews
Delta
8.0
Very good
7,977 reviews

Boarding

8.2

Overall

8.0

Entertainment

7.9

Comfort

7.9

Crew

8.5

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. 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.

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

    Most travelers choose Evansville Dress Regional - Punta Cana, Evansville Dress Regional - San Juan Luis Munoz Marin Intl or Evansville Dress Regional - Montego Bay Sangster Intl 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, September is the cheapest month in which you can book a flight from Evansville to Caribbean (average of $254). Flying from Evansville to Caribbean 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

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 July 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$284Average$629FlexibilityNo cancel feeOn-time71%
DeltaCheapest$371Average$622FlexibilityNo cancel feeOn-timeN/A

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