$125 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 5/11. 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$419
Santo Domingo
Santo Domingo2 stops$563
Montego Bay
Montego Bay2 stops$317
Punta Cana
Punta Cana1 stop$419
Santo Domingo
Santo Domingo2 stops$563
Montego Bay
Montego Bay2 stops$317

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, Aug 11 - Fri, Aug 14
American Airlines Logo
4:21 pm - 1:30 pm
EVV
-
MBJ
21h 09m
2 stops
American Airlines Logo
2:30 pm - 10:32 am
MBJ
-
EVV
20h 02m
2 stops
$317American Airlines
Mon, May 4 - Tue, May 19
Multiple Airlines Logo
7:46 pm - 12:29 am
EVV
-
SJU
27h 43m
2 stops
Multiple Airlines Logo
12:57 pm - 3:49 pm
SJU
-
EVV
27h 52m
1 stop
$323Multiple Airlines
Mon, May 4 - Tue, May 19
Multiple Airlines Logo
7:46 pm - 2:06 pm
EVV
-
SJU
17h 20m
1 stop
Multiple Airlines Logo
12:57 pm - 3:49 pm
SJU
-
EVV
27h 52m
1 stop
$326Multiple Airlines
Mon, May 4 - Tue, May 19
American Airlines Logo
6:56 pm - 12:29 pm
EVV
-
SJU
16h 33m
2 stops
American Airlines Logo
4:25 pm - 10:58 pm
SJU
-
EVV
7h 33m
1 stop
$339American Airlines
Sun, Jul 5 - Fri, Jul 10
American Airlines Logo
6:23 pm - 1:13 pm
EVV
-
MBJ
18h 50m
1 stop
American Airlines Logo
5:17 pm - 12:17 pm
MBJ
-
EVV
19h 00m
2 stops
$343American Airlines
Fri, May 8 - Wed, May 13
American Airlines Logo
6:56 pm - 10:53 am
EVV
-
SJU
14h 57m
2 stops
American Airlines Logo
11:59 pm - 11:38 am
SJU
-
EVV
12h 39m
1 stop
$372American Airlines
Wed, Apr 22 - Tue, Apr 28
American Airlines Logo
6:56 pm - 1:15 pm
EVV
-
STT
17h 19m
2 stops
American Airlines Logo
2:05 pm - 10:35 am
STT
-
EVV
21h 30m
2 stops
$377American Airlines
Tue, Aug 11 - Fri, Aug 14
Delta Logo
10:05 am - 3:34 pm
EVV
-
MBJ
5h 29m
1 stop
Delta Logo
1:14 pm - 10:03 pm
MBJ
-
EVV
8h 49m
1 stop
$513Delta
Wed, Apr 22 - Tue, Apr 28
Delta Logo
6:00 am - 2:48 pm
EVV
-
STT
7h 48m
1 stop
Delta Logo
3:05 pm - 10:42 pm
STT
-
EVV
8h 37m
1 stop
$543Delta
Mon, Aug 24 - Thu, Aug 27
WestJet Logo
6:00 am - 6:30 pm
EVV
-
MBJ
12h 30m
2 stops
WestJet Logo
12:45 pm - 10:03 pm
MBJ
-
EVV
33h 18m
2 stops
$3,507WestJet
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 ($317) and Delta ($513).

Good to know

Low seasonApril
Cheapest flight$125
Best time to beat the crowds with an average 6% drop in price.
Most popular time to fly and prices are also 27% 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 8248 reviews
7.9Comfort
7.8Entertainment
7.2Food
8.1Boarding
8.5Crew
Airline reviews

The whole experience was excellent. As it most often is with Delta

10.0 ExcellentRay, Mar 2026
LGA - MCO
Read more Delta reviews

The whole experience was excellent. As it most often is with Delta

Cabin was not pressurized properly. Several passengers had respiratory difficulties.

I was happy that I was able to get a last minute flight but unfortunately my seat was a middle seat. Even with Delta Comfort I wasn't comfortable

There’s not much to say about a one hour flight. This is a connection from LA to RNO that I missed the previous night due to a mechanical check delay on my originating flight from JFK to LAX. The short flight itself was fine. Instructions from the pilot and crew were per usual. The coffee was barely lukewarm, which possibly was purposeful so we would down it quickly. Bags were already on carousel upon reaching baggage claim, which was excellent.

Flight was warm for first few hours and quite rough

Seat was extremely hard which made even a short 1 hour 20 minute flight fairly uncomfortable.

Everything was good except wifi and a leaking drink chiller. The floor was all wet and my bag was soaked. Did not notice until debarking. Have not heard back from Delta. Even though this was leg one of an international flight in first class, they denied access to their Sky Club - very disappointing!

The staff was fine. The plane was extremely tight, and I paid for the wifi and it did not work at all. I was actually going to ask for a refund.

two hour delay and the Delta representative on the PA system was unable to understand

An awesome flight crew. FC seat cushion just doesn’t cut it for a 3+ hour flight.

Flight delay for mechanical. Inbound arrived on time. No one said why mechanical delay.

Forced to check bags. Crew uninterested in collecting trash. Unclean seats.

why would I bother with this airline and pick seats when I am asked to move for a weight imbalance

Flight pulled out on time but sat on runway for 30 mins. It was extremely cold in the aircraft despite wearing a winter coat. Surprisingly they had a vegetarian meal but could have some better snack choices for a 8 hour flight.

We had a male flight attendant who was super attentive and wonderful! Very professional. I have both gluten and dairy intolerance, and was only able to get a gluten free part, and not the dairy free part of the meal. Easy to order ahead of time and I appreciate being able to do that.

Snow delayed boarding several times, which I understand happens. Issue I had was that after we did board, pilot told us we were going to roll out to be de-iced, then on our way. We were de-iced once, taxied to the tarmac and then stopped. Sat for another 30 minutes or so, the another de-icing. Then we rolled out to a parking spot, only to sit for another hour due to a traffic stop in DCA, which I'm confident they knew would happen before we boarded. Pilot gave no updates other than we had to hold, attendants did speak to the crew, but when asked, said the pilot would be updating us. We on the ground in the plane waiting for over 2 hours. They did communicate that bathrooms would be open, but no other news until we left. Would have been better to be up front about status.

Good crew and flight was on time. It’s a small plane with limited overhead luggage space. They said the overhead space was full and I had to check my bag. There was still space when I got on. Waiting for my checked luggage added 30 minutes to my trip. Not the end of the world but also not great.

My seat was assigned last row behind restrooms No legroom’s I’m very Pettit Still was not comfortable Food choice was excellent

Delayed initially because they couldn’t print the flight details. Poor instruction on delay. When I got on the plane the flight attendant argued with me about whether my carry on would fit (it did, although she didn’t acknowledge that). No greeting (other than arguing with me) getting on or off the plane.

Overall good. The pilots and flight attendants are excellent! The equipment was the issue on my First flight as they had to wait for a part to be installed. So the take off was at least 30 minutes later.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports