$183 Find Cheap Flights from Evansville to Caribbean

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Evansville to Caribbean departing on 8/15. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy

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Best Caribbean Flight Deals from Evansville

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana1 stop$407
Santo Domingo
Santo Domingo1 stop$500
Montego Bay
Montego Bay1 stop$486
Punta Cana
Punta Cana1 stop$407
Santo Domingo
Santo Domingo1 stop$500
Montego Bay
Montego Bay1 stop$486

Cheap Flights from Evansville to Caribbean

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Evansville to Caribbean that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Evansville to Caribbean

Tue, Dec 9 - Mon, Dec 22
American Airlines Logo
5:52 am - 8:45 pmEVV-SJU
12h 53m2 stops
American Airlines Logo
7:20 am - 2:26 pmSJU-EVV
9h 06m1 stop
$372American Airlines
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Fri, Aug 8 - Sun, Aug 17
 Logo
7:19 pm - 8:54 amEVV-PUJ
12h 35m1 stop
 Logo
4:05 pm - 6:39 pmPUJ-EVV
27h 34m2 stops
Tue, Dec 9 - Mon, Dec 22
American Airlines Logo
5:52 am - 5:10 pmEVV-SJU
9h 18m2 stops
American Airlines Logo
2:30 pm - 9:56 pmSJU-EVV
9h 26m2 stops
$412American Airlines
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Fri, Jan 2 - Fri, Jan 9
American Airlines Logo
4:58 pm - 11:45 amEVV-SJU
16h 47m1 stop
American Airlines Logo
7:20 am - 9:48 pmSJU-EVV
16h 28m1 stop
$459American Airlines
Find Deal
Mon, Sep 1 - Mon, Sep 8
American Airlines Logo
6:00 am - 12:31 pmEVV-MBJ
6h 31m1 stop
American Airlines Logo
2:38 pm - 12:37 pmMBJ-EVV
21h 59m2 stops
$486American Airlines
Find Deal
Fri, Jan 2 - Fri, Jan 9
American Airlines Logo
4:58 pm - 10:10 amEVV-SJU
15h 12m2 stops
American Airlines Logo
9:25 am - 9:48 pmSJU-EVV
14h 23m2 stops
$492American Airlines
Find Deal
Fri, Aug 8 - Sun, Aug 17
American Airlines Logo
5:11 pm - 2:10 pmEVV-PUJ
19h 59m2 stops
American Airlines Logo
3:30 pm - 11:28 amPUJ-EVV
20h 58m2 stops
$493American Airlines
Find Deal
Sat, Aug 30 - Sat, Sep 6
Delta Logo
6:10 am - 1:38 pmEVV-SDQ
6h 28m1 stop
Delta Logo
3:03 pm - 9:54 pmSDQ-EVV
7h 51m1 stop
$500Delta
Find Deal
Sat, Aug 30 - Sat, Sep 6
Delta Logo
10:13 am - 12:52 amEVV-SDQ
13h 39m2 stops
Delta Logo
3:03 pm - 9:54 pmSDQ-EVV
7h 51m1 stop
$616Delta
Find Deal
Fri, Jan 2 - Fri, Jan 9
Delta Logo
6:00 am - 4:00 pmEVV-STT
8h 00m1 stop
Delta Logo
3:00 pm - 10:05 pmSTT-EVV
9h 05m1 stop
$631Delta
Find Deal
Booking Insights

KAYAK's insights & trends for Evansville to Caribbean flights

Get data-powered insights and trends into flights from Evansville to Caribbean to help you find the cheapest flights, the best time to fly and much more.

Which airlines provide the cheapest flights from Evansville to Caribbean?

The cheapest round-trip price for the route for each airline clicked by KAYAK users in the last 72 hours.

In the past 3 days, the cheapest round-trip tickets from Evansville to Caribbean were found on American Airlines ($372) and Delta ($500).


Good to know

Low seasonSeptember
High seasonMarch
Cheapest flight$183
Best time to beat the crowds with an average 9% drop in price.
Most popular time to fly with an average 13% increase in price.
Flight from Evansville to Santo Domingo

FAQs - booking Caribbean flights

  • How does KAYAK find such low prices on flights from Evansville to Caribbean?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Evansville to Caribbean.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Evansville to Caribbean?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Evansville to Caribbean is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Evansville to Caribbean?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from Evansville to Caribbean with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Evansville to Caribbean?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Evansville to Caribbean up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • What is the cheapest time of day to fly to Caribbean?

    The cheapest time of day to fly to Caribbean is generally in the afternoon, when round-trip flights cost $394 on average. Morning departures are around 9% cheaper than evening flights, on average. The most expensive time of day to fly to Caribbean is generally in the evening, which is peak travel time and where the average cost of a ticket is $604.

Reviews of the top airlines flying from Evansville to Caribbean

 
Need help choosing which airline to fly with from Evansville to Caribbean? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
DeltaOverall score based on 7958 reviews
8.5Crew
7.9Entertainment
7.3Food
8.2Boarding
7.9Comfort
Airline reviews

There was no problems, just a little uncomfortable with seats that do not lay back a little

8.0 ExcellentWillie, Jul 2025PHX - DTW
Read more Delta reviews

There was no problems, just a little uncomfortable with seats that do not lay back a little

Always good but we must do something about people in rows ahead of you that don't put their seats back up when they are suppose to. And It's rough to not be able to even lean over to get something out of my purse.

Flight was delayed, 30+ bags had to be gate checked. Crew were very friendly!

Everything was good until we were boarding our connection flight in Atlanta, we were told to gate check our carry-on, but when we got inside the plane, there was plenty of room in the overhead.

Did not know my son and I had different seating arrangements. He was fine, but it was disappointing.

Flight was canceled, and no effort was made to help with rebooking, no hotel vouchers, no car transportation and minimal food voucher and most places for food were closed by the time the voucher was given. Waited for 3 hours for bags. Simply the worst travel experience I have ever had

Food was surprisingly good but the WiFi was not great

this crew didn't care much. bumping carts into seats more times than i care to remember

Very late arrival at PWM. Late jet getting to ATL. Equipment problem with aircraft - could not get enough water onto plane., Another delay getting FAA approval for flight with bottled H2O. Not the crew’s problem.

Everything was fine except the entertainment was not working for half of the flight.

Delayed flight, so I switched fights to SFO to Phoenix , Phoenix to DSM. Excellent service through American Airlines

I didn't like that my paid for seat was changed 2 hours before my flight.

The flight had a delay that made me being in a real rush to take the second flight. The delay was almost for 2 hours. They moved us from gate to gate in 4 times. Once I arrived to Philadelphia, I got to run thorough all the airport, as the train was already closed by that time. So I got sick with asthma for all the running I had to do. And I was the last one to board, when it was almost closed. So irresponsable with the people

Flight was delayed and after being in the airport for like seven hours, it was canceled.

Overall fine, but the delay was annoying and the reasons for the delay were not communicated. The crew on board were phenomenal!

Flight delays numerous times. Everytime we would get close to boarding it would be delayed again. Strung along the entire time.

After a two hour delay, my flight was CANCELLED! No pilot available. Such BS.

Overall very good, only complaint I have is the crew from CLT to SAT could have collected trash sooner.

The AA app really sucks ... Every flight & connecting flights were delayed over 30 mins. One connecting flight on American Eagle said it was delayed in its arrival ... when it was actually parked across from the gate for over 1 hr before they pulled it to the gate. Seats in the economy/ main cabin are packed together like sardines ... no leg room.

Initial flight was cancelled at the time of arrival to the airport, flight alternative requires switching from direct to flight with a layover, and the plane felt like it would split apart, it was so rattle-y.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports

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