Find cheap flights from Evansville to Caribbean

Find cheap flights from Evansville to Caribbean

Round-trip
Economy
Evansville (EVV)
Caribbean
Tue 3/2
Tue 3/9
Any month
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Good to know

Low season

July Best time to beat the crowds with an average 4% drop in price.

High season

October Most popular time to fly with an average 9% increase in price.

Average price round-trip

$744 (avg. price over the last 2 weeks)

Good deal round-trip

$616 or less

Top tips for finding cheap flights to Caribbean

  • Book at least 2 weeks before departure in order to get a below-average price.
  • High season is considered to be November and December. The cheapest month to fly to Caribbean is August.
  • Morning departure is around 42% more expensive than an evening flight, on average*.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

FAQs - booking Caribbean flights

How long is the flight to Caribbean from Evansville?

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Top 3 airlines serving Evansville Dress Regional to Caribbean

Scores according to KAYAK customer reviews

7.9
Delta
Overall score based on 29,040 reviews
8.1
Boarding
7.8
Comfort
8.5
Crew
7.8
Entertainment
7.5
Food
Airline reviews

Pros: "On time arrival and departure."
Cons: "Under the Covid circumstances, it was a good experience."

Pros: "Thanks for choosing customer safety over profits. I specifically chose Delta because they continue to not sell the middle seats."

Pros: "Safe, uneventful flight. Everything was great!"
Cons: "Nothing"

Pros: "Delayed"

Pros: "Amazing crew"

Pros: "Crew was good. Seat uncomfortable and hard."

Cons: "Drink service"

Cons: "Delayed 4 hours on tarmack"

Pros: "Crew were helpful and cheerful."
Cons: "Flight on time! Missed connections. In hotel overnight. Missed the event I was travelling to attend!"

Pros: "The fight was very professionally carried out."
Cons: "The gate agent hurried ineffectively to board our slightly delayed flight (around 10 min). She left open the Priority Lane and boarded all pax there, having to step 4 steps to the left to scan every boarding pass."

Pros: "Almost 3 hours of delayed"
Cons: "Almost"

Pros: "Crew was great"
Cons: "flight was diverted an hour away for refueling because of weather over SLC. But SLC opened before we even landed at Grand Junction, CO. I had 8 mins to run between concourses to catch the next flight. My bags didn’t make the flight and have perishable food items. But it is what it is."

Cons: "No delay"

Cons: "Todo excelente!!!gracias!!!"

Pros: "Good communication about weather and delay"
Cons: "No delay. Consider dropping the $75 standby fee."

Pros: "The entertainment was nice."
Cons: "If the screen wasn’t behind the seat. I could hear the tapping of the person behind me."

Pros: "Each leg of the flight didn't take as long as initially purported."
Cons: "The second leg of the flight from Seattle to Honolulu was rough. The plane was very outdated and the female flight attendant in comfort plus did not have any customer service. She repeatedly skipped our row, even with the call light on. For a long flight, especially with Delta this is unacceptable"

Pros: "The crew were kind and courteous. The seat was comfortable."

Pros: "Crew was helpful and food was good."

Pros: "This was my daughter’s first solo travel home from college. She said the staff was helpful and kind. She loved that the flight was not over crowded. It was a smooth flight."
Cons: "Only negative thing she could say was her flight was delayed an hour. But that isn’t terrible considering all the holiday travelers."

Pros: "Boarding was super quick, as crew wanted to leave before the strong rains and winds came through, so we left early! Plane itself was very modern and surprisingly comfortable, as much as a small space can be. Good amount of entertainment, and the crew were pleasant. And flight itself was smooth with very little turbulence which helps!"
Cons: "Had to pay for food, which was a little annoying considering the cost of the flight. Entertainment was very American led... but I guess not surprising considering it’s delta."

Cons: "Need vegetarian meal in first class"

Pros: "It was a smooth boarding, flight and exit out of the plane."

Pros: "On time"
Cons: "Small aircraft"

Cons: "Gas fume on the back seats are horrible"

Pros: "Didn’t major it on the flight. Sleeping in Atlanta. Not the house I paid for in totrtola."
Cons: "Terrible planning. Didn’t have enough fuel to circle. Took a stupid path. 10 minutes cost me a day."

Cons: "The flight was fine, but there was no onboard entertainment. Fortunately the Wi-Fi worked so I was able to stream."

Pros: "Friendly staffs and on time flights"

Pros: "Comfortable seats. Good entertainment"
Cons: "Going to Denver was delayed and now return trip delayed We were give 3 separate reasons. Poor communication. Just telling me a flight will be delayed is not communication. Lack of a free snack was disappointing. May have to rethink flying Delta next time."

Cons: "Overall the flight was good. It would be nice to see if we are Lincoln and Wi-Fi and the greatest selection of movies to its offerings."

Pros: "Excellent leg room. Comfy seat"
Cons: "Seat couldn't recline back. Was a little uncomfortable for a long flight. Chair had crumbs on it before I sat down-it was easily wiped away meaning no one had cleaned the chairs or looked at them beforehand. Absolutely freezing. Wearing long socks and boots and my feet still felt frozen by the end."

Pros: "Funny people at the gate, all was smooth and on time"
Cons: "It was too hot in the cabin, which is unusual (usually, I freeze)"

Pros: "In flight movies"
Cons: "The flight was 3 hours late taking off which made us miss our connection to chicago so we are stuck in Atlanta tonight with unplanned expenses we were not planning on!"

Cons: "Delayed"

Pros: "Free meals and entertainment"
Cons: "Can someone please improve airline food?!"

Pros: "Nothing"
Cons: "The staff"

Pros: "We were treated very well and it was a short, sweet flight. Nothing to complain about."

Pros: "Short flight"
Cons: "Too cold Not friendly boarding agent"

Pros: "I liked the selection of movies."
Cons: "The arrival estimate was off."

Pros: "Great gate agent at JFK on the layover."
Cons: "No assigned seats on second flight til we got to JFK."

Pros: "it was great experience"

Cons: "The flight got delayed by 3 hours or more. I missed my flight from LA to FL"

Pros: "On time!"

Pros: "It was my husband's birthday and the stewardess (red dress, long brown hair) went out of her way to make him feel special by bringing champagne, cookies and even chocolate once we were getting off the plane. I was very touched."
Cons: "The guy next to me was kind of smelly but was very nice."

Pros: "The only flight that was a bit better was from Mumbai to Hyderabad."
Cons: "Almost the entire trip, due to the following reasons: 1. The online check in process didn't work at all. The Delta staff at the Boston airport weren't pleasant and courteous at all. 2. Poor coordination between Delta & Jet Airways - the meal preference was selected before flight at the Jet Airways website but the same didn't get registered properly, even though the website confirmed to me that it was all set. This resulted in appropriate food not being available to the customer on the flight from Boston to Amsterdam. The customer had to literally starve on the flight. 3. The pursers and stewards on the flight from Boston to Amsterdam weren't pleasant and courteous at all. For anything they were asked, their responses ."

Pros: "It was my first time to fly Air France. They exceeded my exceptions. The service was great and they made sure we were very comfortable. I will definitely fly Air France again."

Pros: "The Economy seats with added space Plenty of space Cheerful crew"
Cons: "Nothing"

Pros: "Got Home !"
Cons: "Waited one hour sitting on board the aircraft for it to be fueled!! That's not what you want to do when you have to get home! The aircraft should be ready! And already fueled!"

Pros: "Very friendly flight attendants and for the most part I could understand the pilot when he spoke."
Cons: "Wi-fi should be free. Put chocolate into the snack options."

Pros: "Everything"
Cons: "No comments"

Pros: "The price."
Cons: "Flight was delayed for 2 hours in Airbus 777 full of passengers. The reason was to fix some light and administrative error on a log book. This could have been prevented if they had done all of the checks beforehand. All of those passengers stuck in a plane during a pandemic. Not very smart !!!!"

Pros: "On time take off and the fact that we arrived alive."
Cons: "Hot meals and inflight entertainment. No even drinks were served."

Pros: "Great service and comfortable; well sanitized."
Cons: "TV screens for movies and shows."

Cons: "Both flights were overbooked. Social distancing doesn’t apply to American Airlines."

Cons: "Almost 4 hour delay."

Cons: "The flight sat on the ground well over an hour after landing. No gate was available. Many missed their connections. Miserable."

Pros: "Crew was snappy in getting people in plane and checking in carry ons since occupancy had been reached."
Cons: "Lack of adjustable headrest on seat."

Pros: "Smooth ride"

Cons: "Feeling of being cramped"

Cons: "Todo bien"

Pros: "Service from crew was fine"
Cons: "No delay! Got notification that our flight was one half hour earlier. Then boarded aircraft, and it had electrical problems. Delayed. We had to get off. Then board another aircraft."

Pros: "Checking in with my Mum who needs assistance was excellent."
Cons: "Lack of Entertainment."

Pros: "Time of flight"
Cons: "Aircraft had no screen, old, uncomfortable"

Cons: "Crampt space, cold cabin"

Pros: "None"
Cons: "Long delay"

Pros: "Movie options were good."
Cons: "The a/c was not working well and t"

Pros: "Reliability that your flight will not be cancelled. Punctuality."
Cons: "They charge you $125 for a dog in cabin (JetBlue and Southwest near $100, Frontier $75). There is NO benefit, even with this extra amount of money. I was assigned to enter the aircraft in Group 8... I suggest AA the benefit to enter (at least) in Group 5 for people with PAID in cabin dogs."

Pros: "Service"
Cons: "Seats and space"

Cons: "Entertainment via internet could NEVER be really be done complitly. And the flight attendants did not know how to help costumers"

Pros: "Turkey sandwich snd boarding went smoothly"
Cons: "There was no entertainment and since there is no WiFi for most of the flight due to being over water the flight seemed longer than what it actually was."

Cons: "Poor service"

Pros: "I liked that we got to San Juan safely. The crew on board was very accommodating."
Cons: "Due to the delays, we missed our jumper flight and American refused to compensate. Also, only had two cookies all day from 8:05am until 3:45 pm! No sandwiches as promised. We were delayed approximately 4 hours total. Had to take a taxi ($85) to Fajardo to HOPEFULLY catch last ferry to Culebra. Guess AmericansAirlines doesn’t care if you have to sleep at the dock!"

Cons: "Dallas to San Juan San Juan Dallas American Airlines has the worst seat of any airline flown by us fare almost 2000 dollars for round trip and the seat is small hard uncomfortable even for a short flight this is no business class!!"

Pros: "On time"
Cons: "Cold cabin"

Cons: "The seats are very tight."

Cons: "Last minute cancellation and reschedule if original flight with 20 people hounding the gate for standby status. Craziness. These last minute revisions mist stop"

Pros: "Direct flight"
Cons: "Horrible customer service, excessive baggage fees, rude counter staff, no leg room, narrow seats"

Pros: "USB Outlets are nice to have"
Cons: "Nothing was bad on this flight"

Pros: "Boarding process"
Cons: "Delay, no food,"

Pros: "Can't think of anything good"
Cons: "SEE: Customer Relations request #1-249830721"

Pros: "Nice crew clean airplane"
Cons: "Initial flight was cancelled after 2 hours delay. My next flight was scheduled the earliest possible by AA which was 24 hours later. No transportation,hotel or miles compensation for this. I had work and responsabilities the next day. TThe scheduled trip was supposed to take off at 7:45. Boarding started late and was very slow. My bag fit the meassurements and still was forced to check it (which I did not want to do as I did not want to be waiting an hour for my bag at my arrival as I had work early the next day. In addition there was airplaine traffic as it was "rush hour" instead of flying at 7:45 we departed almost at 9pm!!!! Have to pay for food Quality of tv monitors very poor And in an uncomfortable position No movie options No wifi although stated the aircraft has Non functioning electrical plug"

Pros: "Fast boarding."
Cons: "Slow on return of gate checked bags. A little late in getting off the ground."

Pros: "On time smooth"

Pros: "The pilot was a riot, the flight was on time. Again, nothing wrong, nothing special. As it should be (if only we had more leg and seat room, and I am pretty streamline)."

Pros: "Friendly staff. Landed early. Offered a free bag."
Cons: "They moved the flight earlier, which was not fun. And, there were no entertainment centers."

Pros: "Nothing"
Cons: "Super old planes, no had a tv."

Pros: "Puntuality"

Cons: "There seets are two small. And they dont sell alcohol. That sucks."

Cons: "The airline had trouble with the plane. After we waited 3 hrs in the plane they cancel the flight. They offer a hotel but it was very dirty"

Pros: "Nothing. My fight from San Juan to Miami on Friday Oct. 7 was cancelled because of hurricane Matthews, since I didnot buy a roundtrip with AA they did not reimburse or offer me a credit for my returning flight. I contacted AA in two ocassions and both times their personnel were impersonal and even rude to me with the whole situation. I ended up losing $250 because of choosing American Airlines. I will do my best to avoid traveling with American ever again, and I will spread the word, as well. I felt robbed, so unfair."
Cons: "Everything"

Pros: "Nice staff"
Cons: "I have no complaints"

Cons: "No have owned screen TV"

Pros: "Even when the plane was full they managed to help passengers to get seated."
Cons: "If you still flying economy class, why would you have to pay extra for exit row where the seats are the same. Only received pretzel and a cup of drink on a 3 hour flight once."

Pros: "Everything"
Cons: "Nothing"

Pros: "Comfortable seat"
Cons: "Lack of entertainment"

Pros: "Overall good flight"
Cons: "I did not like the time needed for boarding/ settling in. But that is a factor of people not following instructions. Not the crew."

Pros: "I was going home"
Cons: "Late flight no pilots andt broke my luggage."

Cons: "Gg"

Pros: "Everything was on time, no delays."

Pros: "The food options and that we were offered drinks multiple times."
Cons: "Nothing! It was excellent"

Pros: "Nothing"
Cons: "Not having so many delay and not seating on a plane for over an hour to take off."

Pros: "Friendly crew"
Cons: "Leaving crying babies at home..."

Pros: "Crew was very nice!!"
Cons: "Space on seat not comfortable for tall people"

Cons: "Seats could have been better. Very uncomfortable seats"

Pros: "Nothing"
Cons: "Plane on time and it was very hot on the plane"

Cons: "Again, left stranded in SC."

Pros: "The crew was helpful and nice."
Cons: "It was delayed a lot."

Pros: "Comfortable seats with a touch screen with plenty to choose from to entertain. Updates from the cockpit often. Good music as we boarded and exited the plane to set the mood. Very attentive staff. Would love to fly with United again, soon."

Pros: "Crew was very nice"
Cons: "Sits are very uncomfortable"

Pros: "All in the prices!!! Accesibility!!!"
Cons: "The prices changes too much!"

Pros: "Nothing"
Cons: "I'm supposed to bring a carry on with me and they don't allowed me this time. They should be strict with other passengers who bring more than a carry on. I was SO MADDD"

Cons: "we took off over 1 hour late"

Pros: "Services , on time"

Pros: "All the way we had a great atencion from all the crew and airport facility thanks"

Cons: "See above."

Pros: "They gave me something to drink..."
Cons: "Didn't give us peanuts or any snack items and everything else had to be paid for which I think the pricing on those items were expensive that is abusive unacceptable and me as a military personnel I think there should be some kind of consideration in all those matters including paying for luggage $25..."

Pros: "Great service, it had been a while since I flew with United. Impressed with the new plane."

Pros: "clean; good movies"
Cons: "no kosher food option"

Pros: "Estaba supuesto ser un viaje barato y puntual"
Cons: "Pero no fue de esa manera yo soy un paciente esquizofrénico y padezco de vipolarida más tengo problema con el azúcar mas padezco de sleeping adnnea.y muchas otras condiciones.y mi vuelo no salió cuando. Tenía que salir.yo vivo en perth ambos y era muy difícil viajar para Mi en tren para luego tener que pasar todo lo que pase.deverian por lo menos recomendarme con algo desierta por todos mis inconvenientes."

Pros: "On time and comfort"

Cons: "My seat was the last line and it was uncomfortable."

Pros: "That i had all four seat available to me and very helpful"

Pros: "Was fast and on time"
Cons: "Pushing back from gate took for ever due to mechanical problems and somebody got sick on the plane so their decision to wait until the person situation got better affected everyone else"

Pros: "very helpful"

Pros: "The service & how comfortable I was."
Cons: "That you have to pay for everything but I guess now a days every airline is doing the same thing."

Cons: "The guy putting his feet on me next to the window"

Cons: "Thr boarding process was a mess, a lot of people didn't even have seats assigned."

Pros: "The personal are very amability"

Pros: "Love the crew!"

Pros: "Smooth ride and on time staff was great"
Cons: "I didn't like that I had to pay for my luggage that was really horrible they find anywhere to nickel and dime you but glad they let mine be a carry on"

Cons: "The delays was horrible!!"

Pros: "Fast and easy boarding"
Cons: "No tv, no , no magazines"

Pros: "United personal quickly found our bag location and made the arraingement to send it to us ASAP."
Cons: "The fact that the only bag we checked in with the airline did not arrived in our plane with out any warning what so ever."

Pros: "On time, friendly crew and very reliable"
Cons: "Where's the food?? Gas prices have dropped significantly but all airlines still skimp on food, charge for bags and tickets are still pricey"

Pros: "Everything was perfect, the crew was fantastic"
Cons: "Maybe a bit of food."

Cons: "The airline is horrible.. Poor customer service"

Pros: "Boarding"
Cons: "Excellent"

Pros: "The service since I am handicap"

Pros: "Nothing"
Cons: "Horrible phone customer serviceI."

Cons: "Comfortable and affordable!"

Pros: "What I like the most was that it was on time, also the crew was amicable."

Pros: "Very organized . On time"

Pros: "Everything! My grandparents needed special assistance with wheelchair and the crew was very helpful! They spoke Spanish and they were able to get a crew member to translate"

Pros: "Good trip"
Cons: "Nothing"

Cons: "They did not have TV and no wifi it was terrible. They only gave me a cup of soda nos even a potato chips which other airline do give."

Cons: "Departure from Chicago was delayed"

Pros: "Getting from point a to point b."
Cons: "Lack of good free snacks. Not getting free bag checked."

Pros: "All very happy staff and super professional service."

Pros: "Boarding process"
Cons: "No food... Sporadic drinks.. Very cheap service"

Read more about Delta
COVID-19 information

Safety measures for airlines flying from Evansville to Caribbean

Airlines flying from Evansville to Caribbean have enacted additional safety measures and adjusted policies to better accommodate travelers. Policies vary by airline.

Heightened sanitation

Daily cleaning, installation of cabin HEPA filters on flights from Evansville to Caribbean

Mandatory masks

Masks required on board, masks provided on flights from Evansville to Caribbean

Social distancing seating

Middle seats unavailable to book on flights from Evansville to Caribbean

Pre-flight testing

Testing for antibodies, testing for symptoms for flights from Evansville to Caribbean

Book cheap flights from Evansville to Caribbean

Recent round-trip flight deals

5/12
Wed
2 stops
American Airlines
15h 38m
EVV - SJU
5/18
Tue
2 stops
American Airlines
12h 20m
SJU - EVV
5/12
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American Airlines
15h 38m
EVV - SJU
5/18
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American Airlines
12h 20m
SJU - EVV
4/23
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American Airlines
16h 14m
EVV - SJU
4/28
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American Airlines
17h 39m
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5/12
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American Airlines
15h 38m
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5/18
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American Airlines
12h 20m
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15h 38m
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American Airlines
17h 30m
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5/12
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Multiple Airlines
8h 26m
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12h 20m
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6h 25m
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Delta
7h 40m
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23h 34m
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Recent one-way flight deals

3/8
Mon
2 stops
American Airlines
18h 18m
EVV - SJU
3/8
Mon
1 stop
American Airlines
7h 08m
EVV - SJU
3/22
Mon
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American Airlines
19h 50m
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3/22
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American Airlines
19h 05m
EVV - SDQ
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