$133 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 4/23. 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 Cana1 stop$440
Montego Bay
Montego Bay1 stop$312
Punta Cana
Punta Cana1 stop$440
Montego Bay
Montego Bay1 stop$312

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

Mon, May 4 - Tue, May 19
American Airlines Logo
6:56 pm - 12:29 pm
EVV
-
SJU
16h 33m
2 stops
American Airlines Logo
7:25 am - 10:58 pm
SJU
-
EVV
16h 33m
1 stop
$299American Airlines
Mon, Jun 8 - Sat, Jun 13
American Airlines Logo
4:33 pm - 11:03 am
EVV
-
SJU
17h 30m
2 stops
American Airlines Logo
12:59 am - 5:59 pm
SJU
-
EVV
18h 00m
1 stop
$306American Airlines
Sat, Apr 25 - Wed, Apr 29
American Airlines Logo
6:56 pm - 11:24 am
EVV
-
MBJ
16h 28m
1 stop
American Airlines Logo
1:15 pm - 11:54 pm
MBJ
-
EVV
10h 39m
1 stop
$312American Airlines
Sat, Apr 25 - Wed, Apr 29
American Airlines Logo
4:13 pm - 11:51 am
EVV
-
MBJ
19h 38m
2 stops
American Airlines Logo
12:56 pm - 10:35 am
MBJ
-
EVV
21h 39m
2 stops
$317American Airlines
Mon, May 4 - Tue, May 19
Multiple Airlines Logo
7:46 pm - 8:49 am
EVV
-
SJU
12h 03m
1 stop
Multiple Airlines Logo
7:05 pm - 3:49 pm
SJU
-
EVV
21h 44m
1 stop
$325Multiple Airlines
Tue, Mar 17 - Tue, Mar 24
American Airlines Logo
6:01 pm - 10:56 am
EVV
-
SJU
15h 55m
2 stops
American Airlines Logo
4:25 pm - 11:46 pm
SJU
-
EVV
8h 21m
1 stop
$339American Airlines
Sun, May 24 - Fri, May 29
American Airlines Logo
5:30 pm - 4:35 am
EVV
-
SJU
10h 05m
1 stop
American Airlines Logo
12:59 am - 6:01 pm
SJU
-
EVV
18h 02m
1 stop
$345American Airlines
Mon, Mar 9 - Tue, Mar 17
Multiple Airlines Logo
7:46 pm - 6:00 pm
EVV
-
PUJ
21h 14m
1 stop
Multiple Airlines Logo
7:15 pm - 2:21 pm
PUJ
-
EVV
44h 06m
2 stops
$459Multiple Airlines
Fri, Mar 20 - Fri, Mar 27
Delta Logo
6:00 am - 3:40 pm
EVV
-
PUJ
8h 40m
1 stop
Delta Logo
3:50 pm - 10:23 pm
PUJ
-
EVV
7h 33m
1 stop
$1,077Delta
Sat, Mar 28 - Sat, Apr 4
WestJet Logo
11:19 am - 12:49 pm
EVV
-
MBJ
49h 30m
2 stops
WestJet Logo
1:50 pm - 5:18 pm
MBJ
-
EVV
27h 28m
2 stops
$1,884WestJet
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.

How long does a flight from Evansville to Caribbean take?

The duration of a flight to Caribbean depends on your arrival airport. The shortest routes to Caribbean from Evansville are to Saint Thomas Island, which takes 6h 41m, Montego Bay, which takes 8h 19m, and Punta Cana, which takes 8h 40m.

Good to know

Low seasonAugust
Cheapest flight$133
Best time to beat the crowds with an average 6% drop in price.
Most popular time to fly and prices are also 20% lower on average.
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 8203 reviews
8.1Boarding
7.9Comfort
7.2Food
7.8Entertainment
8.5Crew
Airline reviews

Good experience and the flight landed early. There was no food I had or entertainment.

8.0 ExcellentDavid, Feb 2026
BOS - LGA
Read more Delta reviews

Good experience and the flight landed early. There was no food I had or entertainment.

Flight was delayed and no reasons provided. After the passengers were boarded, the crew made announcement that the captain has jot arrived and he would take another 15 mins. All passengers patiently sat until the captain came and started. Terrible experience!

Flight was delayed. No information on why it was delayed. After we boarded the flight, , the crew made announcement that the captain hs not arrived and he will take 15 mins more to arrive. Passengers were just sitting patiently for the captain to arrive and start, Terrible experience.

Totally worth the miles to upgrade to Delta Comfort. Plenty of legroom.

This was my first time flying Delta ever and I had a great experience!

Smallest leg room I've ever had on a plane.

They took all carry-on luggage from Groups 6 -9 - I was group 5 and waiting in line to board - they made me check my luggage too. That then went to baggage claim and delayed departure from the airport. There was overhead room in my seating area - Delta over reacted. Also, had a gentleman next to me that took up 1/2 my seat.

Excellent!!! Aeromexico is a great airline. What was not that good is the service provided by Kayak. It is never clear and not easy to manage.

Flight delay was frustrating, also you cannot checkin online without delta app, web browser check-in throw errors

The gate agent was most helpful in getting me on to fly standby. I greatly appreciate it.

Boarding delayed 20 minutes for no reason, no wifi, in flight entertainment, or snacks / waters?

Didn't get a seat assignment until the last minute even though i picked a seat.

American has been able to implement an algorithm that makes it possible for nearly every one of my evening flights to be late. Congratulations!

I was on a small regional flight from Detroit to Philadelphia. When we landed the outside cruise needed to turn something off with the engine, which took quite a long time. Then, when they allowed us to get off the plane it was outside. They took their time, unloading all the luggage and waited till they unloaded all the luggage before they brought it over to us. It was 9 o’clock at night freezing cold out, and there was no proactive hustle to try to get people their luggage. It was really one of the worst experiences I think I’ve ever had with American until a manager came over. I don’t think they were going to even consider pulling the luggage over to the people that had been waiting outside for at least 10 minutes in the freezing cold.

The flight was fine, once we got underway. It was more than hour delayed

Beverage service was not good. Also just one service in 5 hr 30 min flight. No ask fir water ir anything beside one time beverage service.

Waited for oxygen tanks for 30 minutes after boarding was complete.

The seats are too uncomfortable for anyone over 5ft 8in. I'm 5'10" with a back and hip issue and I was in pai for the full duration of the flight.

The flight was on time/early, attentive crew, and everything overall went smoothly. Disappointed that WIFI was not working for the flight.

One day, I do so hope for a gluten free snack! Seems like with the rest of the world FINALLY figuring out what gluten free is, American Airlines would too. Fingers crossed!!

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports