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$244+ 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 11/20. Fares are subject to change and may not be available on all flights or dates of travel.
EVV — SJU
Nov 27 — Dec 41
Thu 11/27
Thu 12/4
1 adult, Economy
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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 October 28, 2025.

This American Airlines deal was found by Cheapflights users on 10/25. 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.
Mon 11/106:43 amEVV - SJU
2 stops15h 15mAmerican Airlines
Fri 11/1412:55 pmSJU - EVV
2 stops11h 56mAmerican Airlines
Deal found 10/25$399
This Kiwi.com deal was found by Cheapflights users on 10/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/105:35 pmEVV - SJU
1 stop7h 19mMultiple Airlines
Thu 11/133:59 amSJU - EVV
1 stop14h 56mMultiple Airlines
Deal found 10/25$421
This American Airlines deal was found by Cheapflights users on 10/26. 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 12/1612:06 pmEVV - SJU
2 stops20h 03mAmerican Airlines
Tue 12/236:00 amSJU - EVV
1 stop13h 27mAmerican Airlines
Deal found 10/26$453
This American Airlines deal was found by Cheapflights users on 10/26. 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.
Wed 12/176:45 amEVV - SJU
1 stop13h 24mAmerican Airlines
Wed 12/246:00 amSJU - EVV
1 stop10h 15mAmerican Airlines
Deal found 10/26$475
This Kiwi.com deal was found by Cheapflights users on 10/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/238:04 pmEVV - SJU
1 stop13h 34mMultiple Airlines
Sat 11/293:59 amSJU - EVV
1 stop29h 35mMultiple Airlines
Deal found 10/26$505
This American Airlines deal was found by Cheapflights users on 10/26. 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 11/811:03 amEVV - SJU
1 stop8h 21mAmerican Airlines
Sun 11/163:43 pmSJU - EVV
1 stop10h 11mAmerican Airlines
Deal found 10/26$562
This American Airlines deal was found by Cheapflights users on 10/27. 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.
Sat 12/273:47 pmEVV - PUJ
1 stop22h 57mAmerican Airlines
Thu 1/11:27 pmPUJ - EVV
1 stop12h 21mAmerican Airlines
Deal found 10/27$788
This American Airlines deal was found by Cheapflights users on 10/26. 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.
Mon 10/275:19 pmEVV - STT
2 stops21h 46mAmerican Airlines
Mon 11/34:35 pmSTT - EVV
2 stops19h 31mAmerican Airlines
Deal found 10/26$821
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 12/265:10 amEVV - PUJ
1 stop9h 34mAmerican Airlines
Wed 12/311:27 pmPUJ - EVV
1 stop9h 23mAmerican Airlines
Deal found 10/28$1,257
This WestJet deal was found by Cheapflights users on 10/26. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/106:07 amEVV - MBJ
2 stops36h 16mWestJet
Wed 12/178:25 pmMBJ - EVV
2 stops38h 01mWestJet
Deal found 10/26$4,699

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 October 28, 2025.

Round-trip from

$368
(American Airlines)

One-way from

$244
(Mytrip)

Popular in

January

Cheapest in

October

Average price

$285
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. 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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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 October 28, 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

Mon 3/9

4:56 pm-12:35 pm

2 stops18h 39m

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

Mon 11/10

6:43 am-11:58 pm

2 stops15h 15m

San Juan Luis Munoz Marin Intl

Fri 11/14

12:55 pm-10:51 pm

2 stops11h 56m

$399

EvansvilleSaint Thomas Island

EVV - STT

EVVSTT

Evansville Dress Regional

Sun 1/4

2:32 pm-2:28 pm

1 stop21h 56m

Saint Thomas Island Cyril E King

Sat 1/10

4:06 pm-6:20 pm

1 stop28h 14m

$408

EvansvilleSan Juan

EVV - SJU

EVVSJU

Evansville Dress Regional

Mon 11/10

5:35 pm-2:54 am

1 stop7h 19m

San Juan Luis Munoz Marin Intl

Thu 11/13

3:59 am-4:55 pm

1 stop14h 56m

$421

EvansvilleSan Juan

EVV - SJU

EVVSJU

Evansville Dress Regional

Tue 12/16

12:06 pm-10:09 am

2 stops20h 03m

San Juan Luis Munoz Marin Intl

Tue 12/23

6:00 am-5:27 pm

1 stop13h 27m

$453

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

1:15 pm-9:56 am

2 stops21h 41m

$460

EvansvilleSan Juan

EVV - SJU

EVVSJU

Evansville Dress Regional

Wed 12/17

6:45 am-10:09 pm

1 stop13h 24m

San Juan Luis Munoz Marin Intl

Wed 12/24

6:00 am-2:15 pm

1 stop10h 15m

$475

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

5:18 pm-11:26 am

2 stops20h 08m

$478

EvansvilleSaint Thomas Island

EVV - STT

EVVSTT

Evansville Dress Regional

Wed 1/14

3:30 pm-3:56 pm

2 stops22h 26m

Saint Thomas Island Cyril E King

Mon 1/19

6:39 pm-4:18 pm

2 stops23h 39m

$509

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

11:35 am-10:05 pm

1 stop10h 30m

$531

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/27

Showing 1-10 of 17 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.

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, January is the cheapest month in which you can book a flight from Evansville to Caribbean (average of $167). Flying from Evansville to Caribbean 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

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 October 28, 2025.
Peruse reviews from past customers who have flown with Delta and American Airlines 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
7.9
Good
7,994 reviews

Food

7.3

Crew

8.5

Entertainment

7.9

Comfort

7.9

Boarding

8.2

Overall

7.9

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
7,994 reviews
Delta
7.9
Good
7,994 reviews

Food

7.3

Crew

8.5

Entertainment

7.9

Comfort

7.9

Boarding

8.2

Overall

7.9

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
11,032 reviews
Delta
7.9
Good
7,994 reviews

Food

7.3

Crew

8.5

Entertainment

7.9

Comfort

7.9

Boarding

8.2

Overall

7.9

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. 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.

  • How long is the flight from Evansville to Caribbean?

    There are many flights that can get you from Evansville to Caribbean in 18h 39m. Fly via American Airlines or Delta to get the fastest option. There are 1874 mi between Evansville and Caribbean. This flight may include one or multiple stops.

  • 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, January is the cheapest month in which you can book a flight from Evansville to Caribbean (average of $167). Flying from Evansville to Caribbean 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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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 October 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$275Average$587FlexibilityNo cancel feeOn-time71%
DeltaCheapest$371Average$556FlexibilityNo cancel feeOn-timeN/A

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