$319 Find Cheap Flights from Evansville to Caribbean

This is the cheapest round-trip flight price found by a KAYAK user in the last 72 hours by searching for a flight from Evansville to Caribbean departing on 2/6. 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

KAYAK searches hundreds of travel sites at once for deals on flights to Caribbean

Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 23% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Free to useThere are no hidden charges or fees.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flight Deals
Booking Insights
Flight Deals

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$477
Santo Domingo
Santo Domingo2 stops$543
Montego Bay
Montego Bay2 stops$3,530
Punta Cana
Punta Cana1 stop$477
Santo Domingo
Santo Domingo2 stops$543
Montego Bay
Montego Bay2 stops$3,530

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

Fri, Feb 6 - Fri, Feb 13
Multiple Airlines Logo
7:46 pm - 9:47 am
EVV
-
SJU
12h 01m
1 stop
Multiple Airlines Logo
12:27 pm - 7:06 pm
SJU
-
EVV
8h 39m
1 stop
$283Multiple Airlines
Fri, Feb 6 - Fri, Feb 13
Multiple Airlines Logo
7:46 pm - 8:24 pm
EVV
-
SJU
22h 38m
2 stops
Multiple Airlines Logo
11:52 am - 7:06 pm
SJU
-
EVV
9h 14m
1 stop
$312Multiple 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
5:28 am - 3:49 pm
SJU
-
EVV
11h 21m
1 stop
$319American Airlines
Tue, Mar 17 - Tue, Mar 24
American Airlines Logo
7:07 am - 7:39 pm
EVV
-
SJU
11h 32m
2 stops
American Airlines Logo
5:28 am - 3:49 pm
SJU
-
EVV
11h 21m
1 stop
$346American Airlines
Tue, Mar 17 - Tue, Mar 24
American Airlines Logo
7:07 am - 8:50 pm
EVV
-
SJU
12h 43m
2 stops
American Airlines Logo
7:40 am - 3:49 pm
SJU
-
EVV
9h 09m
2 stops
$383American Airlines
Fri, Feb 6 - Fri, Feb 13
American Airlines Logo
4:51 pm - 10:48 am
EVV
-
SJU
15h 57m
2 stops
American Airlines Logo
2:30 pm - 11:53 pm
SJU
-
EVV
11h 23m
2 stops
$409American Airlines
Wed, May 20 - Wed, May 27
Delta Logo
6:00 am - 3:21 pm
EVV
-
STT
8h 21m
1 stop
Delta Logo
1:20 pm - 10:05 pm
STT
-
EVV
9h 45m
1 stop
$621Delta
Tue, Feb 24 - Thu, Mar 12
Delta Logo
6:00 am - 2:17 pm
EVV
-
SDQ
6h 17m
1 stop
Delta Logo
6:35 am - 10:23 pm
SDQ
-
EVV
16h 48m
2 stops
$634Delta
Mon, Feb 2 - Fri, Feb 6
WestJet Logo
11:40 am - 7:17 pm
EVV
-
MBJ
30h 37m
2 stops
WestJet Logo
2:55 pm - 11:48 am
MBJ
-
EVV
21h 53m
2 stops
$3,530WestJet
Mon, Feb 2 - Fri, Feb 6
WestJet Logo
11:40 am - 7:17 pm
EVV
-
MBJ
30h 37m
2 stops
WestJet Logo
2:55 pm - 11:48 am
MBJ
-
EVV
21h 53m
2 stops
$3,535WestJet
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 ($319) and Delta ($634).

Good to know

Low seasonSeptember
Cheapest flight$283
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 8051 reviews
8.1Boarding
8.5Crew
7.2Food
7.9Comfort
7.8Entertainment
Airline reviews

The seats weren’t reclining even though it wasn’t as exit seat

6.0 GoodPuneet, Jan 2026
MSP - EWR
Read more Delta reviews

The seats weren’t reclining even though it wasn’t as exit seat

It was good because we traveled without luggage, carry on only.

I usually get upgraded so my experience is usually amazing. I did not get upgraded this time - which was fine - but the wifi had issues, the monitors were going in & out, & (though not Delta's fault) one of the gentlemen next to me desperately needed a shower.

The entertainment screens were not working and there was no air condition the entire flight. Very uncomfortable.

I have diamond medallion status and usually we are in comfort plus . We were in main this time ( which was fine ) and my husband wanted wine . I have at least 10 vouchers for drinks that are good for this year and next! The attendant would not take the picture of the voucher as proof and never came back to check as She asked me to pull it up on delta Wi-Fi. Instead my husband just used his Amex to buy the wine . Disappointing!!!

Food is basically Sun Chips, cookies or Cheezits. I had an exit row seat so I had plenty of room. The crew was very nice and efficient. Pilot kept us informed. Pretty good flight.

Air travel sucks. It continues to be awful for all airlines. No shame on delta alone.

It was Delta, but the flight attendants were stressful and disrespectful. I am a diamond member a travel weekly. I have not had a negative thing to share in quite some time. But this was noticeable.

Comfort Plus seat 11E seemed smaller than prior flights. The movie selection is good. Watched most of the most recent Tron movie. I'll watch the remaining part later as my movie is saved in the Delta Seatback Experience.

Flight was late from Newark to Atlanta, I asked flight attendant to please let my family of 3 out first when we landed to Atlanta because we were late for our connecting flight to Quito. She didn't and we were late for 5 minutes we couldn't board the plane and spend hours trying to get another flight with customer service for the next day.

AA should improve their in air internet & entertainment options. Seems unreasonable to charge $20/hr and should have some form of free connections. The entertainment options are also pretty limited, movies are outdated and the series only show 3-5 episodes.

The professionals have excellent customer service, the seats don´t have enough space.

We were upgraded to First Class and it was a great flight

Amazing I love American. I’ll never fly anyone else if I can help it.

I love American. I’ll never fly anyone else if I can help it.

Flight delay and multiple gate changes including a change near boarding time to another terminal, which in DFW is a pain. Pre-boarding delay and also a further delay on the ground after boarding. About an hour and a half total delay.

On the plus side, crew was attentive, drinks were cold, and in-flight entertainment selection was better than some other airlines. On the negative aide, Plane was delayed almost an hour, either no announcements from the gate crew. Biscoff cookies are gross, appreciate airlines that give a choice. Also, crew had no personality or enthusiasm at all.

Little warm on the plane and delayed for an hour

Tell the crew (when boarding) to yell at the imbeciles blocking us from walking up to scan. I promise everyone crowds around and half of us (most the time I’m group 4) have to push our way through. Your staff is awesome, the public - not so much-

Bags took over and hour to come out. Delays due to wind caused rebooking.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports