$168 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 7/5. 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$588
Santo Domingo
Santo Domingo2 stops$675
Montego Bay
Montego Bay1 stop$357
Punta Cana
Punta Cana1 stop$588
Santo Domingo
Santo Domingo2 stops$675
Montego Bay
Montego Bay1 stop$357

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, Sep 23 - Wed, Sep 30
American Airlines Logo
5:45 pm - 3:07 pm
EVV
-
SJU
20h 22m
2 stops
American Airlines Logo
6:27 am - 11:29 pm
SJU
-
EVV
18h 02m
2 stops
$331American Airlines
Wed, Aug 19 - Wed, Aug 26
American Airlines Logo
6:00 am - 1:12 pm
EVV
-
MBJ
7h 12m
1 stop
American Airlines Logo
2:12 pm - 11:59 pm
MBJ
-
EVV
9h 47m
1 stop
$357American Airlines
Wed, Aug 19 - Wed, Aug 26
American Airlines Logo
5:01 pm - 1:52 pm
EVV
-
MBJ
20h 51m
2 stops
American Airlines Logo
12:47 pm - 11:27 pm
MBJ
-
EVV
10h 40m
1 stop
$362American Airlines
Wed, Sep 23 - Wed, Sep 30
American Airlines Logo
6:39 am - 2:50 pm
EVV
-
SJU
7h 11m
1 stop
American Airlines Logo
4:38 pm - 12:23 pm
SJU
-
EVV
20h 45m
2 stops
$371American Airlines
Tue, Aug 18 - Tue, Aug 25
Delta Logo
10:04 am - 3:34 pm
EVV
-
MBJ
5h 30m
1 stop
Delta Logo
2:26 pm - 10:01 pm
MBJ
-
EVV
7h 35m
1 stop
$422Delta
Sat, Aug 1 - Fri, Aug 7
American Airlines Logo
4:35 pm - 11:04 am
EVV
-
SJU
17h 29m
2 stops
American Airlines Logo
12:55 am - 5:20 pm
SJU
-
EVV
17h 25m
1 stop
$449American Airlines
Tue, Jul 14 - Tue, Jul 21
American Airlines Logo
4:35 pm - 11:47 am
EVV
-
MBJ
19h 12m
2 stops
American Airlines Logo
2:09 pm - 12:20 pm
MBJ
-
EVV
22h 11m
2 stops
$457American Airlines
Thu, Aug 20 - Thu, Aug 27
Delta Logo
10:04 am - 3:34 pm
EVV
-
MBJ
5h 30m
1 stop
Delta Logo
1:09 pm - 10:01 pm
MBJ
-
EVV
8h 52m
1 stop
$550Delta
Thu, Jul 2 - Sun, Jul 5
Multiple Airlines Logo
8:16 pm - 8:25 pm
EVV
-
PUJ
23h 09m
1 stop
Multiple Airlines Logo
11:35 am - 7:43 am
PUJ
-
EVV
21h 08m
1 stop
$647Multiple Airlines
Wed, Aug 19 - Thu, Aug 27
LATAM Airlines Logo
5:59 pm - 4:40 pm
EVV
-
MBJ
22h 41m
2 stops
LATAM Airlines Logo
5:40 pm - 1:02 pm
MBJ
-
EVV
19h 22m
2 stops
$1,701LATAM Airlines
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 seasonAugust
Cheapest flight$168
Best time to beat the crowds with an average 9% drop in price.
Most popular time to fly and prices are also 22% 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 8416 reviews
7.8Entertainment
7.2Food
7.8Comfort
8.5Crew
8.1Boarding
Airline reviews

No service flight that took 5 hrs and a stop at an unscheduled airport. Crew and pilots did their jobs

6.0 GoodAnonymous, May 2026
ATL - ECP
Read more Delta reviews

No service flight that took 5 hrs and a stop at an unscheduled airport. Crew and pilots did their jobs

Clean planes and not take my comfort class seat away.

The crew were efficient. The pilots seemed professional. It was a bit chilly in our seats. The sheet provided weren’t very helpful.

Weather caused a long delay, but the efficiency and updates from the pilot were helpful. We were able to make our connection fortunately.

Planes were clean, no water or snacks on either flight.

Free & relatively fast Wi-Fi. Would've liked a wider drink selection.

I continue to be satisfied with Delta’s excellent service out of LGA. The digit id works well and gets me through security in no time. Whenever possible, I choose Delta.

Was revoked with Jet Blue due to delay from Kenya Air

The Boarding process was great. Particularly since my wife and I require assistance. The flight attendants were amazing. We travel frequently; they honestly were a cut above. 😀

Enjoyed it very much. Especially liked the free WiFi that Delta offers.

Movies on my phone are great. It would be nice to have a gluten free snack option.

It was what i expected. I like the movies you can access from your phone. It would be nice if there was a gluten free snack offered. But I did bring my own snack knowing there would not be a gluten free option

The flight was peaceful, just s slight turbulence, pilots and crews were all nice and made a great job! Arrived safely in the Philippines. Thank you ya’ll!

Ontario airport boarding was very easy to park and access, is clean and TSA took 10 minutes total. Check-in was a breeze and cruise was very nice.

American Airlines II: Delay Boogaloo. Multiple gate changes, delays, boarded and then MORE delays. I hate to say this won’t matter, but posting stuff about major corporations in 2026 is a post-modern “scream into the void.” Was multiple hours late coming home, so there you go.

Awful, tons of delays, I got into Chicago multiple hours late meaning I hit the very traffic I tried so desperately to avoid. Just empty apologies from American Airlines text alerts. Trash behavior from a trash airline.

The flight attendants were very friendly, efficient, and helpful. The plane was ahead of schedule, and it all went very smoothly. Thank you.

They lost my baggage and I am still struggling to the information and update

We got delayed getting out of DFW for broken overhead bins. Once the flight got underway the captain kept the seatbelt sign lit the entire flight despite little perceptible turbulence, preventing use of the rest rooms and any sort of refreshment service in the main cabin.

Flight delays for communication overall not a good experience uncomfortable on the plane. Person in front of me reclined his seat, putting them inches from my lap.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports