$133 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 Cana2 stops$419
Santo Domingo
Santo Domingo2 stops$553
Montego Bay
Montego Bay1 stop$312
Punta Cana
Punta Cana2 stops$419
Santo Domingo
Santo Domingo2 stops$553
Montego Bay
Montego Bay1 stop$312

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

Sat, Apr 25 - Wed, Apr 29
American Airlines Logo
6:23 pm - 12:13 pm
EVV
-
MBJ
17h 50m
1 stop
American Airlines Logo
1:15 pm - 11:54 pm
MBJ
-
EVV
10h 39m
1 stop
$312American Airlines
Sat, Apr 25 - Wed, Apr 29
American Airlines Logo
6:56 pm - 11:51 am
EVV
-
MBJ
16h 55m
2 stops
American Airlines Logo
1:15 pm - 11:54 pm
MBJ
-
EVV
10h 39m
1 stop
$317American Airlines
Thu, May 7 - Mon, May 11
American Airlines Logo
11:03 am - 8:51 pm
EVV
-
SJU
8h 48m
1 stop
American Airlines Logo
11:59 pm - 11:38 am
SJU
-
EVV
12h 39m
1 stop
$372American Airlines
Wed, Apr 8 - Wed, Apr 15
American Airlines Logo
6:56 pm - 1:15 pm
EVV
-
STT
17h 19m
2 stops
American Airlines Logo
1:15 pm - 11:28 pm
STT
-
EVV
11h 13m
1 stop
$400American Airlines
Thu, May 7 - Mon, May 11
American Airlines Logo
6:18 am - 9:24 pm
EVV
-
SJU
14h 06m
2 stops
American Airlines Logo
11:59 pm - 11:38 am
SJU
-
EVV
12h 39m
1 stop
$412American Airlines
Tue, Apr 14 - Tue, Apr 21
American Airlines Logo
5:50 pm - 1:02 pm
EVV
-
PUJ
18h 12m
2 stops
American Airlines Logo
3:34 pm - 10:35 am
PUJ
-
EVV
20h 01m
2 stops
$419American Airlines
Thu, Apr 9 - Thu, Apr 16
Multiple Airlines Logo
4:28 pm - 8:25 pm
EVV
-
PUJ
26h 57m
1 stop
Multiple Airlines Logo
9:13 pm - 7:06 pm
PUJ
-
EVV
22h 53m
2 stops
$441Multiple Airlines
Tue, Mar 17 - Tue, Mar 24
Delta Logo
6:00 am - 4:18 pm
EVV
-
SJU
9h 18m
1 stop
Delta Logo
2:44 pm - 10:23 pm
SJU
-
EVV
8h 39m
1 stop
$490Delta
Tue, Aug 11 - Thu, Aug 27
Delta Logo
10:05 am - 12:57 am
EVV
-
SDQ
13h 52m
2 stops
Delta Logo
2:37 pm - 10:03 pm
SDQ
-
EVV
8h 26m
1 stop
$714Delta
Tue, Aug 11 - Thu, Aug 27
Delta Logo
6:00 am - 1:12 pm
EVV
-
SDQ
6h 12m
1 stop
Delta Logo
2:37 pm - 10:03 pm
SDQ
-
EVV
8h 26m
1 stop
$771Delta
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 ($312) and Delta ($490).

Good to know

Low seasonAugust
Cheapest flight$133
Best time to beat the crowds with an average 6% drop in price.
Most popular time to fly and prices are also 18% 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 8237 reviews
7.2Food
7.8Entertainment
7.9Comfort
8.1Boarding
8.5Crew
Airline reviews

2+hrs delay without any reason provided and a cramped flight

2.0 MediocreYogendra Kumar, Feb 2026
DTW - MDT
Read more Delta reviews

2+hrs delay without any reason provided and a cramped flight

We waited an hour on the runway to get a gate in Orlando

Flight was delayed by 3-hours and their fix was… complimentary pretzels.

Flight was delayed due to crew being not on time

Flight crew issues delayed my flight by 2 1/2 hours. Causing me to miss my connection.

The staff on board and gate was nice - a welcome change from the usual. We also arrived early, which was a great benefit, given that it takes 30 minutes plus to get bags at SRQ.

The staff was frielndly. The plane was terrible, it was too small and should be decommissioned. There were no back seat screens at all. The only beverages we had a choice from was coffee, tea or water. The only bathroom in the back was behind the flight attendant's jump seat and wasn't working. And I literally felt like I was sitting on top of the guy next to me. It was terribly hot in the plane and we had to sit on the tarmac in Chicago for 1/2 hour due to congestion in Mpls. Wouldn't they have know that before they even boarded us so that we could have sat in comfort in the terminal?

Never got on it. Was re-routed through Detroit and am still in airports 12 hours later waiting for my connecting plane to arrive.

Delta has too many delays now days. It is 1:06 am now. I was supposed to land in Norfolk at 10:30 pm. I got re-booked through Detroit and I’m still in Detroit. I hope to be landed in Norfolk by 3am. I’ve been in airports for 12 hours as of right now. There is a weather delay now but most delays lately have been maintenance.

Very Very late. Subsequent flights left an hour before ours

Flight boarded, departed and landed on time. Excellent service from flight attendant in FIRST

Boarding is always an ordeal. Less dogs on flights. I am highly allergic to dogs and cats. Why are there so many animals these days?

Flight to Tampa was delayed taking off due to plane arriving late but no other issues

There was a delay with the plan which cause the flight to leave later and once arrived in Chicago there was another delay and some passengers missed their connecting flights

Massimo, flight attendant was very authentic, attentive - wonderful. Food/wrap was just okay.

Worst experience ever. Flight could not land in Charlotte for what we were told was a ground stop. Had to be diverted to Raleigh to refuel. Strangely during ground stop, our connecting flight had no issue taking off on time causing us to miss our flight. We were told there were no other flights that day to our final destination and that two days out was the next one. The only flights to get us there were from Chicago the next morning. Completely opposite direction but it was a direct flight. So we get flown to Chicago and have to find a hotel in our own dime. The flight in the morning was also delayed. Thankfully only a short time. The non too of all this, our luggage did not arrive by the time we were there. Communication was terrible, through the entire trip. Complete incompetence. Will never fly American again.

Horrible. Got delayed many hours because their pilot wasn't trained for night landing at the airport and a rain delay made it a night landing. We have to wait hours for a qualified crew. They give us 12 dollar meal vouchers but most everything in the airport was closed and definitely more expensive than the vouchers.

I am an AA flyer for a very long time... AA has yet to disappoint.

Flight was delayed. Not much information on when the flight would take off. Eventually we were told it was maintenance. App was not giving updates.

Never ontime and always delays. Long waits for customer service and often app doesn’t work

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports