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$138+ 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 5/17. Fares are subject to change and may not be available on all flights or dates of travel.
EVV — SJU
Feb 27 — Mar 61
Thu 2/27
Thu 3/6
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 February 22, 2025.

Round-trip from

$247
(Mytrip)

One-way from

$138
(Delta)

Popular in

November

Cheapest in

September

Average price

$400
From Evansville Dress Regional to Caribbean
Search Deals
One-way flight from Evansville Dress Regional to Caribbean
Search Deals
Highest demand for flights based on searches. 4% potential increase in price ($23 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($16 potential savings vs. average RT price).
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Average for round-trip flights in February 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 February 22, 2025.

This Mytrip deal was found by Cheapflights users on 2/21. 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.
Fri 5/167:09 pmEVV - SJU
1 stop13h 47mMultiple Airlines
Sun 5/182:06 amSJU - EVV
1 stop17h 23mMultiple Airlines
Deal found 2/21$247
This Delta deal was found by Cheapflights users on 2/21. 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.
Fri 5/166:00 amEVV - SJU
1 stop9h 30mDelta
Tue 5/207:30 amSJU - EVV
1 stop10h 27mDelta
Deal found 2/21$275
This American Airlines deal was found by Cheapflights users on 2/21. 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 12/304:58 pmEVV - SJU
1 stop16h 47mAmerican Airlines
Sat 1/106:30 amSJU - EVV
2 stops10h 55mAmerican Airlines
Deal found 2/21$315
This American Airlines deal was found by Cheapflights users on 2/22. 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 3/126:14 amEVV - PUJ
1 stop8h 10mAmerican Airlines
Wed 3/263:50 pmPUJ - EVV
1 stop7h 57mAmerican Airlines
Deal found 2/22$455
This American Airlines deal was found by Cheapflights users on 2/21. 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 10/57:06 pmEVV - STT
2 stops16h 44mAmerican Airlines
Fri 10/105:15 pmSTT - EVV
2 stops17h 52mAmerican Airlines
Deal found 2/21$519
This Delta deal was found by Cheapflights users on 2/21. 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.
Fri 3/2111:41 amEVV - MBJ
1 stop8h 56mDelta
Tue 3/257:00 amMBJ - EVV
1 stop9h 49mDelta
Deal found 2/21$541
This Mytrip deal was found by Cheapflights users on 2/21. 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.
Mon 3/246:42 pmEVV - PUJ
2 stops19h 00mMultiple Airlines
Sat 3/2912:59 pmPUJ - EVV
2 stops25h 35mMultiple Airlines
Deal found 2/21$608
This American Airlines deal was found by Cheapflights users on 2/21. 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 3/214:25 pmEVV - MBJ
2 stops19h 35mAmerican Airlines
Tue 3/2510:15 amMBJ - EVV
2 stops11h 42mAmerican Airlines
Deal found 2/21$635
This American Airlines deal was found by Cheapflights users on 2/22. 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 6/144:53 pmEVV - SDQ
2 stops18h 57mAmerican Airlines
Tue 7/13:30 pmSDQ - EVV
2 stops19h 19mAmerican Airlines
Deal found 2/22$636
This Delta deal was found by Cheapflights users on 2/22. 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 6/146:00 amEVV - SDQ
1 stop6h 11mDelta
Tue 7/12:30 pmSDQ - EVV
1 stop8h 35mDelta
Deal found 2/22$780
This WestJet deal was found by Cheapflights users on 2/21. 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.
Mon 4/76:16 amEVV - MBJ
2 stops36h 07mWestJet
Mon 4/141:50 pmMBJ - EVV
2 stops32h 31mWestJet
Deal found 2/21$1,722

Find flights from Evansville to Caribbean within your budget

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 February 22, 2025.

Fly from

Evansville

Fly to

Caribbean

Route

Depart

Return

Price

EvansvilleSan Juan

EVV - SJU

EVVSJU

Evansville Dress Regional

Fri 5/16

7:09 pm-9:56 am

1 stop13h 47m

San Juan Luis Munoz Marin Intl

Sun 5/18

2:06 am-6:29 pm

1 stop17h 23m

$247

EvansvilleSan Juan

EVV - SJU

EVVSJU

Evansville Dress Regional

Fri 5/16

6:00 am-4:30 pm

1 stop9h 30m

San Juan Luis Munoz Marin Intl

Mon 5/19

6:15 am-12:55 pm

1 stop7h 40m

$275

EvansvilleSan Juan

EVV - SJU

EVVSJU

Evansville Dress Regional

Wed 4/2

3:44 pm-5:00 am

1 stop12h 16m

San Juan Luis Munoz Marin Intl

Sat 4/5

5:30 am-3:57 pm

2 stops11h 27m

$342

EvansvillePunta Cana

EVV - PUJ

EVVPUJ

Evansville Dress Regional

Wed 3/12

6:14 am-3:24 pm

1 stop8h 10m

Punta Cana

Wed 3/26

3:50 pm-10:47 pm

1 stop7h 57m

$455

EvansvilleMontego Bay

EVV - MBJ

EVVMBJ

Evansville Dress Regional

Fri 3/21

11:41 am-8:37 pm

1 stop8h 56m

Montego Bay Sangster Intl

Tue 3/25

7:00 am-4:49 pm

1 stop9h 49m

$541

EvansvillePunta Cana

EVV - PUJ

EVVPUJ

Evansville Dress Regional

Mon 3/24

6:42 pm-2:42 pm

2 stops19h 00m

Punta Cana

Sat 3/29

12:59 pm-1:34 pm

2 stops25h 35m

$608

EvansvilleMontego Bay

EVV - MBJ

EVVMBJ

Evansville Dress Regional

Fri 3/21

4:25 pm-12:00 pm

2 stops19h 35m

Montego Bay Sangster Intl

Tue 3/25

10:15 am-10:47 pm

1 stop12h 32m

$635

EvansvilleSanto Domingo

EVV - SDQ

EVVSDQ

Evansville Dress Regional

Sat 6/14

4:53 pm-12:50 pm

2 stops18h 57m

Santo Domingo Las Americas

Tue 7/1

3:30 pm-9:49 am

2 stops19h 19m

$636

EvansvilleSanto Domingo

EVV - SDQ

EVVSDQ

Evansville Dress Regional

Sat 6/14

6:00 am-1:11 pm

1 stop6h 11m

Santo Domingo Las Americas

Tue 7/1

2:30 pm-10:05 pm

1 stop8h 35m

$780

EvansvilleSaint Thomas Island

EVV - STT

EVVSTT

Evansville Dress Regional

Thu 5/22

4:57 pm-10:55 am

1 stop16h 58m

Saint Thomas Island Cyril E King

Fri 5/30

5:04 pm-10:11 am

2 stops18h 07m

$817

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/21

Showing 1-10 of 14 results
1
2

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.

Travel insights for flights from Evansville to Caribbean

Get recent, data-driven insights about flights from Evansville to Caribbean including ideal travel times, pricing trends, and more.

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 March is currently the most expensive (average of $363). 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.

Rainfall in Caribbean by month

Plan your trip to Caribbean by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Caribbean ranges from 2.2 - 6.1 inches per month. November is typically the wettest month, when rainfall can reach 6.1 in. February is typically the driest time to visit Caribbean when rainfall is around 2.2 in.

Temperature in Caribbean by month

Plan your trip to Caribbean by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Caribbean, use this chart to help with planning. For those seeking warmer temperatures, June is the ideal time of year to visit, when temperatures reach an average of 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 77.0 F).

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 February 22, 2025.
Delta
8.0
Very good
8,203 reviews

Boarding

8.2

Crew

8.5

Comfort

8.0

Entertainment

7.9

Food

7.3

Overall

8.0

Reviews

1 / 20

10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

Delta
8.0
Very good
8,203 reviews
Delta
8.0
Very good
8,203 reviews

Boarding

8.2

Crew

8.5

Comfort

8.0

Entertainment

7.9

Food

7.3

Overall

8.0

Reviews

1 / 20

10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
8,203 reviews

Boarding

8.2

Crew

8.5

Comfort

8.0

Entertainment

7.9

Food

7.3

Overall

8.0

Reviews

1 / 20

10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

WestJet
7.2
Good
2,800 reviews
Delta
8.0
Very good
8,203 reviews

Boarding

8.2

Crew

8.5

Comfort

8.0

Entertainment

7.9

Food

7.3

Overall

8.0

Reviews

1 / 20

10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

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 - San Juan Luis Munoz Marin Intl, Evansville Dress Regional - Punta Cana 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 March is currently the most expensive (average of $363). 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

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Alternative routes for Evansville to Caribbean

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 February 22, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$284Average$770FlexibilityNo cancel feeOn-time71%
DeltaCheapest$371Average$795FlexibilityNo cancel feeOn-timeN/A
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