$326 Find Cheap Flights from Evansville to Caribbean - Compare and Save

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 10/27. 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$587
Montego Bay
Montego Bay1 stop$372
Punta Cana
Punta Cana2 stops$587
Montego Bay
Montego Bay1 stop$372

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

Tue, Oct 27 - Tue, Nov 3
American Airlines Logo
12:27 pm - 11:33 pm
EVV
-
SJU
10h 06m
1 stop
American Airlines Logo
2:41 pm - 11:59 pm
SJU
-
EVV
11h 18m
2 stops
$326American Airlines
Fri, Sep 25 - Sun, Oct 4
American Airlines Logo
5:45 pm - 1:54 pm
EVV
-
SJU
19h 09m
2 stops
American Airlines Logo
4:38 pm - 9:54 am
SJU
-
EVV
18h 16m
2 stops
$366American Airlines
Sun, Nov 1 - Wed, Nov 4
American Airlines Logo
7:05 pm - 1:14 pm
EVV
-
MBJ
17h 09m
1 stop
American Airlines Logo
3:14 pm - 11:30 pm
MBJ
-
EVV
9h 16m
1 stop
$372American Airlines
Sun, Nov 1 - Wed, Nov 4
American Airlines Logo
3:45 pm - 12:55 pm
EVV
-
MBJ
20h 10m
2 stops
American Airlines Logo
1:55 pm - 10:36 am
MBJ
-
EVV
21h 41m
2 stops
$377American Airlines
Fri, Aug 7 - Fri, Aug 14
American Airlines Logo
6:25 pm - 1:12 pm
EVV
-
MBJ
18h 47m
1 stop
American Airlines Logo
2:37 pm - 11:50 am
MBJ
-
EVV
21h 13m
2 stops
$383American Airlines
Fri, Sep 25 - Sat, Oct 3
American Airlines Logo
5:45 pm - 1:54 pm
EVV
-
SJU
19h 09m
2 stops
American Airlines Logo
3:35 pm - 11:29 pm
SJU
-
EVV
8h 54m
1 stop
$450American Airlines
Fri, Sep 25 - Sat, Oct 3
Delta Logo
10:00 am - 4:49 pm
EVV
-
SJU
5h 49m
1 stop
Delta Logo
7:00 am - 2:56 pm
SJU
-
EVV
8h 56m
1 stop
$468Delta
Fri, Aug 7 - Fri, Aug 14
American Airlines Logo
6:25 pm - 1:12 pm
EVV
-
MBJ
18h 47m
1 stop
American Airlines Logo
12:47 pm - 11:27 pm
MBJ
-
EVV
10h 40m
1 stop
$482American Airlines
Sat, Nov 7 - Sat, Nov 14
American Airlines Logo
11:03 am - 12:07 pm
EVV
-
STT
23h 04m
2 stops
American Airlines Logo
4:18 pm - 10:36 am
STT
-
EVV
20h 18m
2 stops
$485American Airlines
Fri, Sep 25 - Sun, Oct 4
Delta Logo
1:43 pm - 10:19 pm
EVV
-
SJU
7h 36m
1 stop
Delta Logo
12:56 pm - 9:49 pm
SJU
-
EVV
9h 53m
1 stop
$622Delta
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.

What is the cheapest month to fly from Evansville to Caribbean?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Evansville to Caribbean, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Evansville to Caribbean is October, when tickets cost $235 (return) on average. On the other hand, the most expensive months are February and September, when the average cost of round-trip tickets is $729 and $549 respectively.

Good to know

Low seasonSeptember
Cheapest flight$326
Best time to beat the crowds with an average 19% drop in price.
Most popular time to fly and prices are also 32% 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.
7.8
DeltaOverall score based on 8453 reviews
7.8Comfort
8.5Crew
8.1Boarding
7.2Food
7.8Entertainment
Airline reviews

FA was a bit strange and dodgy not very characteristic of Delta

6.0 GoodSaad, Jun 2026
LGA - ATL
Read more Delta reviews

FA was a bit strange and dodgy not very characteristic of Delta

Not really a “Delta” problem but worth mentioning: Boarding was a difficult process. TSA seemed understaffed and Pre-Check took longer than regular TSA. The supervisor was frazzled and yelled at travelers. Once through TSA, we had to put our carry-ons through another x-ray machine. Then queue up to board with both boarding pass and ID. Then, when we got to the stairs on the tarmac, we had to show our boarding pass again. Maybe this is just normal for Kona since the terminal is outdoors (but still a “secured” area).

flight was delayed 4+ hours. there was really no understanding of why? weather? the last hour of delay was post boarding. pilot seat was broken. was that the real reason? nonetheless, long day of inconveniences.

Love me some Delta. One of the few airlines to recognize and support veterans. Easy boarding, flight was on time and arrived early and the flight attendants were excellent on this flight.

WiFi didn’t work on two of four planes. Flight attendants were not overly friendly or welcoming. Planes were extremely slow to board and deplane.

Flight from Fort Wayne to Atlanta was the smallest in terms of cabin space that I've ever seen. A carry on I've used for 20 years BARELY fit in overhead compartment. I'm 5'10" and felt very cramped. Not the best experience.

Extremely dosappoontined and frustrated. Refused entry to lounge in Detroit despite having Delta AMEX Reserve linked in MyDelta phone app as revommended and also having proof of account. No pillows were available for overnight flight to AMS and breakfast was not served in Delta Comfort.

The airplanes were so old and out-dated it was terrifying to fly on them.

Delta flight overall it was goodT!the crew could do more and the food could be better.

Short flight. Perfect crew. Older plane. But clean and comfortable

The Mario was so helpful and provided amazing customer service however l have being waiting for a callback for almost a week now and have not heard anything further after l informed them l wanted to change my date of traveling because of my hospital appointment even send them proof and l was unable to use manag your booking on their website is a bit frustrating and l would appreciate an update on My request as soon as possible. And have called them times without numbers no response

There is no room, no gluten free options, or any free internet/entertainment. You have to bring your own tablet or smartphone because there are no screens.

April was the flight attendant in first class and was the most pleasant, cordial and efficient person I have seen on a flight in years. Good example of the type of people AA should hire to increase customer satisfacdtion.

Excellent accommodating crew at gate and on board. Baggage claim and gate checking were flawless.

Delayed 6 times. Eventually rebooked and missed a whole day of my vacation. Hot mess

Unfriendly gate staff and significant delay once we were on the plane.

Entertainment was okay not because anything was wrong but it is a short flight so having no wifi is annoying but understandable. Crew was outstanding as usual

I am tired of being nickel and dimed for seat location, checked luggage and carry on bags. That is why i rarely fly anymore.

Did not get to Ontario yet. Sitting on tarmac for 2 plus hours.

Pros: "Gate agent was great"
Cons: "They didn’t have a pilot assigned to our flight. Had to wait 3 hours for a pilot to arrive. 😞. Thank goodness I wasn’t in a hurry to get to my destination."

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports