$128 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$459
Santo Domingo
Santo Domingo2 stops$824
Montego Bay
Montego Bay1 stop$3,423
Punta Cana
Punta Cana1 stop$459
Santo Domingo
Santo Domingo2 stops$824
Montego Bay
Montego Bay1 stop$3,423

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, Mar 30 - Sun, Apr 5
Multiple Airlines Logo
7:46 pm - 1:26 pm
EVV
-
STT
16h 40m
1 stop
Multiple Airlines Logo
2:36 pm - 7:06 pm
STT
-
EVV
29h 30m
1 stop
$319Multiple Airlines
Sun, Aug 23 - Thu, Aug 27
American Airlines Logo
4:21 pm - 11:09 am
EVV
-
SJU
17h 48m
2 stops
American Airlines Logo
3:50 pm - 9:47 pm
SJU
-
EVV
6h 57m
1 stop
$326American Airlines
Sat, Apr 11 - Sat, Apr 18
American Airlines Logo
6:56 pm - 10:48 am
EVV
-
SJU
14h 52m
1 stop
American Airlines Logo
7:25 am - 11:28 pm
SJU
-
EVV
17h 03m
1 stop
$331American Airlines
Mon, Apr 13 - Fri, Apr 17
Multiple Airlines Logo
7:46 pm - 1:26 pm
EVV
-
STT
16h 40m
1 stop
Multiple Airlines Logo
10:49 am - 7:06 pm
STT
-
EVV
9h 17m
1 stop
$356Multiple Airlines
Mon, Mar 30 - Sun, Apr 5
Multiple Airlines Logo
7:46 pm - 1:26 pm
EVV
-
STT
16h 40m
1 stop
Multiple Airlines Logo
4:35 pm - 7:06 pm
STT
-
EVV
27h 31m
2 stops
$358Multiple Airlines
Fri, Apr 17 - Fri, Apr 24
American Airlines Logo
6:56 pm - 10:53 am
EVV
-
SJU
14h 57m
2 stops
American Airlines Logo
11:38 am - 11:54 pm
SJU
-
EVV
13h 16m
2 stops
$366American Airlines
Tue, Jun 2 - Wed, Jun 10
Delta Logo
1:42 pm - 12:23 pm
EVV
-
PUJ
21h 41m
2 stops
Delta Logo
1:45 pm - 12:53 pm
PUJ
-
EVV
24h 08m
2 stops
$629Delta
Thu, Jun 4 - Wed, Jun 10
Delta Logo
1:42 pm - 12:23 pm
EVV
-
PUJ
21h 41m
2 stops
Delta Logo
1:45 pm - 9:26 am
PUJ
-
EVV
20h 41m
2 stops
$634Delta
Mon, Aug 24 - Thu, Aug 27
WestJet Logo
10:05 am - 11:45 am
EVV
-
MBJ
25h 40m
2 stops
WestJet Logo
12:45 pm - 10:03 pm
MBJ
-
EVV
33h 18m
2 stops
$3,752WestJet
Mon, Aug 24 - Thu, Aug 27
WestJet Logo
10:05 am - 11:45 am
EVV
-
MBJ
25h 40m
2 stops
WestJet Logo
12:45 pm - 10:03 pm
MBJ
-
EVV
33h 18m
2 stops
$3,756WestJet
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 ($366) and Delta ($1,507).

Good to know

Low seasonFebruary
Cheapest flight$128
Best time to beat the crowds but there is an average 6% increase in price.
Most popular time to fly with an average 3% 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 8303 reviews
7.9Comfort
7.8Entertainment
8.1Boarding
7.2Food
8.5Crew
Airline reviews

My flight was cencaled due with the bad weather on Sunday the crew was poorly mistaken my luggage supposed depart with my flight instead I didn’t have my luggage for almost 3 days the website is poorly respond to my complain until I have someone to do it my connection smooth their not even respon or email me even the have my luggage

2.0 MediocreJaka, Mar 2026
MSP - SEA
Read more Delta reviews

My flight was cencaled due with the bad weather on Sunday the crew was poorly mistaken my luggage supposed depart with my flight instead I didn’t have my luggage for almost 3 days the website is poorly respond to my complain until I have someone to do it my connection smooth their not even respon or email me even the have my luggage

Delta needs to step its game up get a more reliable internet service. Internet service was non-existent for this flight.

Mechanical Delay of over an hour with multiple gate changes. Entertainment system down for rejuvenation.

This was a Latam operated flight. Seats seemed a bit narrow in business class. Older aircraft.

I had a flight cancel and had it rerouted. When the rerouted they put me at a window seat instead of an isle. It was hard sitting by the window because the couple with masks on were making out. I get motion sickness which is why I need to have the isle seat.

NEVER MADE THE FLIGHT BECAUSE DELTA SAID THEY CAN NOT

THEY FAILED ME AND I NEVER GOT ON THE FLIGHT BECAUSE IT WAS SO DELAYED! I ENDED UP HAVING TO PAY OUT OF POCKET FOR A HOTEL AND STAY IN NASHVILLE TO CATCH A FLIGHT FOR THE FOLLOWING DAY. DELTA IS POOR CUSTOMER SERVICE>

8 hours late and the plane smelled like urine, that smell in the morning when your child wet the bed in the night.

My flight was canceled on Sunday. Rebooking took three hours. Had to pay for accommodations another night. New flight was delayed for 5 hours, all that was sent was a 12 dollar food voucher, which doesn’t tell you how to use it. Then when we landed we had to sit on the plane for an hour before we could get off.

Miserable. This entire round trip was miserable. I booked evening flights to and from Detroit on consecutive days that should have had me at my destination by 10:30. Instead I arrived after 3am on my flight to Detroit and after midnight on my return. Multiple unforced errors like awaiting bags to get put on the plane for almost an hour in Detroit and a 20 minute delay to pull up to the gate in Atlanta has me rethinking my assumption that delta is the best and most reliable airline

It was great. Smooth flight, comfortable, left on time and landed on time.

Perhaps this is an airport issue, but being in a takeoff queue for over an hour in the taxiing lane is unacceptable. We will definitely be seeking alternative avenues for air travel in the future.

We hoarded. Then we deplaned. Then we waited for 10 hours in the MSP airport due to a wheel misfunction. We understand safety but communication between crew and airport staff was horrible. When we did finally board, we were rushed on and because we were waiting for a “fresh” pilot and crew, we sat in a roasting plane with no A/C for an hour. My question is why was this flight not cancelled right away when they knew this would be a huge issue OR, why did AA not get a substitute plane, considering this was already a full flight? To me, this appears to be a complete breakdown in leadership and utter systems failure. The compensation for completely disrupting travel plans for hundreds, which we paid dearly for, was measly. While we appreciated the lodging for the night, $12 in meal vouchers isn’t going to sustain anyone for over 12 hours. “We apologize; our hands are tied” is no longer an acceptable explanation. We are so completely turned off by this experience and will definitely seek alternative avenues when we need to fly.

Mostly good. The WiFi wasn’t working so that was not great.

I rated the experience "mediocre" because of the 2 hour delay in take off. This is the 4th flight from DFW on AA where there was a delay and in one of the instances (after 13 delays), the flight was cancelled. I understand weather but for the March 18th flight, there was no weather issue in Dallas or Detroit. I called Concierge Key and they were wonderful, booking me on a later flight in case my flight was cancelled. I have flown with American for many years and never has there been this consistent pattern of delays. Very disappointing.

They put me on an earlier and I got home sooner

Not good. One of my luggage is missing. And until now they can’t find it

Horrible experience upon landing. Probably more due to DCA utter incompetence than AA.

Jill was the flight attendant in first class she was fabulous!! Best flight attendant I have had in years.!! And I fly every other week. Other can learn from her!!

Really good. I accidentally left my duffel on the plane and the reps were so friendly in retrieving it.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports