$256 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 2/8. 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, 0 bags

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Cheap Flights from Evansville to Caribbean

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana2 stops$462
Montego Bay
Montego Bay1 stop$568
Punta Cana
Punta Cana2 stops$462
Montego Bay
Montego Bay1 stop$568

Book Cheap Evansville to Caribbean Plane Tickets

 
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

Wed, Feb 18 - Tue, Feb 24
Delta Logo
11:14 am - 11:58 pm
EVV
-
SJU
10h 44m
1 stop
Delta Logo
6:15 am - 10:33 am
SJU
-
EVV
6h 18m
1 stop
$256Delta
Mon, Feb 16 - Thu, Feb 19
Multiple Airlines Logo
7:46 pm - 10:17 am
EVV
-
SJU
12h 31m
1 stop
Multiple Airlines Logo
3:53 am - 7:06 pm
SJU
-
EVV
17h 13m
1 stop
$277Multiple Airlines
Mon, Mar 2 - Fri, Mar 6
Multiple Airlines Logo
7:46 pm - 9:54 am
EVV
-
SJU
12h 08m
1 stop
Multiple Airlines Logo
6:30 am - 7:06 pm
SJU
-
EVV
14h 36m
1 stop
$304Multiple Airlines
Fri, Feb 13 - Thu, Feb 19
Multiple Airlines Logo
7:46 pm - 10:17 am
EVV
-
SJU
12h 31m
1 stop
Multiple Airlines Logo
3:53 am - 7:06 pm
SJU
-
EVV
17h 13m
1 stop
$305Multiple Airlines
Fri, Feb 27 - Fri, Mar 6
Multiple Airlines Logo
7:46 pm - 1:24 am
EVV
-
SJU
27h 38m
2 stops
Multiple Airlines Logo
11:04 am - 7:06 pm
SJU
-
EVV
10h 02m
1 stop
$315Multiple Airlines
Mon, Mar 9 - Thu, Mar 12
Multiple Airlines Logo
7:46 pm - 9:17 am
EVV
-
SJU
12h 31m
1 stop
Multiple Airlines Logo
5:30 am - 7:19 am
SJU
-
EVV
26h 49m
1 stop
$320Multiple Airlines
Sun, Feb 15 - Wed, Feb 25
American Airlines Logo
5:10 am - 11:40 pm
EVV
-
SJU
16h 30m
2 stops
American Airlines Logo
7:00 am - 11:28 pm
SJU
-
EVV
18h 28m
2 stops
$324American Airlines
Wed, Mar 18 - Wed, Mar 25
American Airlines Logo
6:57 pm - 2:54 pm
EVV
-
PUJ
18h 57m
2 stops
American Airlines Logo
11:35 am - 6:32 pm
PUJ
-
EVV
7h 57m
1 stop
$462American Airlines
Wed, May 20 - Wed, May 27
Delta Logo
6:00 am - 1:59 pm
EVV
-
STT
6h 59m
1 stop
Delta Logo
1:20 pm - 10:05 pm
STT
-
EVV
9h 45m
1 stop
$550Delta
Sat, Jul 4 - Sat, Jul 11
WestJet Logo
10:05 am - 11:40 am
EVV
-
MBJ
25h 35m
2 stops
WestJet Logo
12:45 pm - 12:51 pm
MBJ
-
EVV
24h 06m
2 stops
$3,560WestJet
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 Delta ($256) and American Airlines ($324).

Good to know

Low seasonSeptember
Cheapest flight$210
Best time to beat the crowds but there is an average 37% increase in price.
Most popular time to fly with an average 18% increase in price.
Flight from Evansville to San Juan

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.

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.
7.9
DeltaOverall score based on 8124 reviews
7.9Comfort
8.5Crew
7.2Food
7.8Entertainment
8.1Boarding
Airline reviews

The flight was comfortable and uneventful, which is what I desire

8.0 ExcellentLarry, Jan 2026
JFK - SJD
Read more Delta reviews

The flight was comfortable and uneventful, which is what I desire

The service from the flight attendants were of supreme quality. They greeted and treated everyone with a wide smile. This is totally absent nowadays. Kudos to them!!!!

Excellent flight and got us around tough weather. Only issue was seat TV did not work and crew tried to reboot.

Very large passenger too space from my own seat. Arm board couldn’t be lowered because of his size. It wads very uncomfortable trip, as the flight was full couldn’t move anywhere having back pain because of the position in which I was the entire flight.

was sitting in the jet bridge for 10 minutes in -20 degree weather waiting for my bag

Outdated equipment in disrepair, wifi inoperable. Broken seats, taped air vents, generally poor condition, the 717 showed its age and lack of upkeep.

My flight out of Baton Rouge to Atlanta was delayed by a half hour. This got us into Atlanta airport 30 minutes late. I ran through the airport to get to my connecting flight. As I approached the boarding gate, I saw the boarding door was still open and a passenger was being checked in. But when I got to the gate, the boarding agent told me they had already given away my seat and there were no empty seats on that flight. So I had to take a later flight. That has never happened to me before. Very frustrating.

Connection through Atlanta was difficult. Mechanical issue on plane caused a two hour delay. New gate was a mile away.

No WiFi. Comfort plus should have alcohol provided, crew only offered water or tea. Who the heck wants tea?

The flight was delayed and oversold. I volunteered to give up my seat for compensation. Thinking I could get a good night's sleep instead of arriving home at 2 am. It took over an hour to get the new reservation confirmed, three different gate attendants, and two red coats. It took even longer to confirm the overnight hotel, and when I arrived, the line was 45 minutes long, with two people checking in, and at least 15 people slowly, very slowly—no food except frozen convenience food, no coupon for food from airlines. Slept, headed back to the airport, and that flight had an equipment change and a gate change just as they were about to board. It took an additional hour to board as they cleaned the plane from storage.

The plane was experiencing problems with the HVAC system, it was very cold in the front of the plane and very hot in the back.

My flight to London from Philadelphia was cancelled due to weather.

The attendants were kind and helpful. A sugar-free drink would have been very welcome.

Pilot navigated severe weather/snow storm with skill. Described his intentions clearly

one crew said "he" didn't serve double alcohol drinks for travelers in exit rows. crew on prior flight did. Is this a AA rule, and the prior crew was being nice? Also, I think we deserve more than a 25% refund for losing first class seats when rescheduling a flight due to weather

It was a little concerning to hear the ground crew arguing with the flight crew over baggage space. Instead of taking them and checking them, they started checking for space in the first class cabin moving items around like the flight crew didn't know what they were doing. I was embarrassed for them.

2 hour delay due to equipment failure. No updates via the app and airport screens (which continued to show a departure time in the past). AA eventually switched planes and the new plane was not catered or cleaned correctly.

I booked an aisle seat and was given a middle. At 6'4" 230lbs, it is not ideal to fly in the middle row for myself and passengers.

Trip delayed for 2 hours because of rain. We boarded and have to get down the flight and reboard again.

The aircraft had several problems - from excess fuel to non operational ac. Two hours of delay in Chicago could have been avoided with proper planning and aircraft maintenance.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports