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Cheap Flights from Indianapolis to Caribbean Islands

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
Punta Cana
Punta Cana2 stops$431
Santo Domingo
Santo Domingo1 stop$554
Montego Bay
Montego Bay1 stop$473
Oranjestad
Oranjestad1 stop$494
Nassau
Nassau1 stop$406
Kingston
Kingston1 stop$814
Simpson Bay
Simpson Bay1 stop$459
Providenciales
Providenciales1 stop$439
Port of Spain
Port of Spain1 stop$586
Bridgetown
Bridgetown1 stop$661
George Town
George Town1 stop$442
Willemstad
Willemstad2 stops$675
Aguadilla
Aguadilla1 stop$294
Puerto Plata
Puerto Plata1 stop$808
St. John's
St. John's1 stop$784
Punta Cana
Punta Cana2 stops$431
Santo Domingo
Santo Domingo1 stop$554
Montego Bay
Montego Bay1 stop$473
Oranjestad
Oranjestad1 stop$494
Nassau
Nassau1 stop$406
Kingston
Kingston1 stop$814
Simpson Bay
Simpson Bay1 stop$459
Providenciales
Providenciales1 stop$439
Port of Spain
Port of Spain1 stop$586
Bridgetown
Bridgetown1 stop$661
George Town
George Town1 stop$442
Willemstad
Willemstad2 stops$675
Aguadilla
Aguadilla1 stop$294
Puerto Plata
Puerto Plata1 stop$808
St. John's
St. John's1 stop$784

KAYAK's insights & trends for Indianapolis to Caribbean Islands flights

Get data-powered insights and trends into flights from Indianapolis to Caribbean Islands to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Indianapolis to Caribbean Islands flight route?

The cheapest ticket to Caribbean Islands from Indianapolis found in the last 5 days was to Punta Cana, at $590 round-trip. The most popular route is from Indianapolis (IND) to Punta Cana (PUJ), and the cheapest round-trip airline ticket found on this route in the last 5 days was $590.

What is the cheapest time of day to fly to Caribbean Islands?

The cheapest time of day to fly to Caribbean Islands is generally in the morning, when round-trip flights cost $552 on average. The most expensive time of day to fly to Caribbean Islands is generally in the morning, which is peak travel time and where the average cost of a ticket is $552.

Can I save money by flying with a layover from Indianapolis to Caribbean Islands?

No, with an average price for the route of $424, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Indianapolis to Caribbean Islands?

The cheapest month for flights from Indianapolis to Caribbean Islands is January, when tickets cost $489 (return) on average. On the other hand, the most expensive months are December and June, when the average cost of round-trip tickets is $706 and $693 respectively.

How far in advance should I book a flight from Indianapolis to Caribbean Islands?

To get a below average price on the flight from Indianapolis to Caribbean Islands, you should book around 2 weeks before departure, which saves you about 20% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 14 weeks before departure.

Good to know

Low season

August
Best time to beat the crowds with an average 5% drop in price.
Most popular time to fly with an average 8% increase in price.

FAQs - booking Caribbean Islands flights

  • How does KAYAK find such low prices on flights from Indianapolis to Caribbean Islands?

    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 Indianapolis to Caribbean Islands.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Indianapolis to Caribbean Islands?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Indianapolis to Caribbean Islands 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 Indianapolis to Caribbean Islands?

    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 Indianapolis to Caribbean Islands 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 Indianapolis to Caribbean Islands?

    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 Indianapolis to Caribbean Islands up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top 5 airlines serving from Indianapolis to Caribbean Islands

 
Need help choosing which airline to fly with from Indianapolis to Caribbean Islands? 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
SouthwestOverall score based on 4214 reviews
8.0Comfort
8.1Boarding
7.5Entertainment
7.0Food
8.6Crew
Airline reviews

A List preferred boarding was nice Asked for a mask and cheerfully received Denver bag check-in is tricky. Not near other checking desk. Have to navigate to east security and up to level six for bag checkin. TSA busy and 20 minutes process thru pre lines Denver train to gates quick but one more thing to plan time for and long concourse walk to gate

10.0 ExcellentRon, Oct 2026
Read more Southwest reviews

A List preferred boarding was nice Asked for a mask and cheerfully received Denver bag check-in is tricky. Not near other checking desk. Have to navigate to east security and up to level six for bag checkin. TSA busy and 20 minutes process thru pre lines Denver train to gates quick but one more thing to plan time for and long concourse walk to gate

Not exactly Southwest’s problem, but the new Burbank airport is not great. No restaurants open and tons of work still to be completed. Can’t believe they opened the airport in that condition.

You made me miss my connecting flight. I can not go to Cleveland on teh revised flight you are sending as I will the entire meeting. I have no option that to fly back. I hope you compensate me for the loss.

Overall great! Internet was a little slow but no other issues.

Horrible communication from Southwest. No accountability. Flight was delayed for 4 hours and TSA closed in the interim. We were not allowed to our gate. Southwest knew this information and did not relay to their customers to arrive to the airport earlier.

Flight boarded 2.5 hours late (my second southwest flight of the day with late departure), the gate agent was grumpy and unhelpful. Said she was "tired so we aren't going to follow normal boarding order". No complaints about the actual flight crew.

Your computers were down and took a long time to check baggage

Southwest has lost most of what made it special. The flight attendants all used to seem fun and like they were having fun. Now they seem just miserable. They do NOT seem happy to give you your pretzels and drinks. They stick it in your hand or on your tray like it's an annoyance. They bark safety instructions at you. It's not just this flight but the last few SW flights I've had to SNA and SAN as well and it's not just me. I've informally surveyed my colleagues (business and leisure travelers) and these feelings are consistent. The tickets are similarly priced to other carriers and the seat assignments make boarding slower. The free luggage and free ability to change flights is still a differentiator. You lose that and there's virtually nothing special left.

Only one drink pass through the cabin for a 4 hour flight. Quite rough and bumpy landing.

Excellent! Only question is how we check in at exactly 24 hours in advance and end up at the end of the B boarding group

Delayed departure, 30min. but arrived nearly on time. Crew was reassuring.

First, off the bat, the Delta gate attendant was rude, inattentive and gave us an attitude when we asked for clarification of our seats for this rebooked flight as we missed our connecting flight due to the delay from Berlin. Flight attendants were all but friendly, rushed through for water refills so you couldn’t even catch them to request more water. Snacks were just OK. Headphones for the movies were so bad that with the airplane noise, the volume of the movie wouldn’t go up enough to even understand the voices. I had to turn on CC to even know what was being said.

Not up to Delta standards. Flight attendant in FC seemed more about just going through the motions than providing friendly customer service. Efficient but mechanical. Never smiled. Never acknowledged pleasantries. Never offered to hang my suit jacket. Just did her tasks. Fine, but not an optimal customer experience. .

Nothing really it’s just the flight availability that hurts sometimes

WiFi didn’t work on two of four planes. Flight attendants were not overly friendly or welcoming. Planes were extremely slow to board and deplane.

Flight from Fort Wayne to Atlanta was the smallest in terms of cabin space that I've ever seen. A carry on I've used for 20 years BARELY fit in overhead compartment. I'm 5'10" and felt very cramped. Not the best experience.

Extremely dosappoontined and frustrated. Refused entry to lounge in Detroit despite having Delta AMEX Reserve linked in MyDelta phone app as revommended and also having proof of account. No pillows were available for overnight flight to AMS and breakfast was not served in Delta Comfort.

The airplanes were so old and out-dated it was terrifying to fly on them.

Delta flight overall it was goodT!the crew could do more and the food could be better.

Short flight. Perfect crew. Older plane. But clean and comfortable

The WiFi went out an hour before the flight was due to land so I did not get my money's worth.

I have been flying united for a long time but now I’m done

It's not United, but TSA security at Terminal A in Newark is a disaster and seriously makes me consider switching to flying out of JFK. The touchless TSA pre-check had a line of over 50 people and the bag screening was so slow that it limited the flow of people through the facial recognition process. It is the only airport that I frequent that has this issue and makes me reconsider whether I should fly out of Newark given the wasted time and frustration it causes. As I said, it is not a United issue but will impact United if people choose to stop utilizing Newark airport because of the poor experience.

The food could be much better. Also very unfortunate that most of business class seats were empty but I could not upgrade.

Requested for warm or hot water because of throat pain, it was denied. The entertainment system was hung, requested the crew to turn it off, instead of turning it off they rebooted the device. It was stuck again, no one bothered to check.

Horrible on the chicago end. They change hates then there is a plane at the new gate so we can’t pull in. Then that plane has mechanical issue and needs to be pulled back to the gate but we can’t get to another new gate due the other plane being in the way. Horrible gate management which will cause many customers to miss connections.

- delayed because video screens not working - delayed getting a gate at DCA Just continued bad experience IAH to DCA.

Bag got checked but I thought one personal item was guaranteed.

Not a bad flight but a long delay boarding and taking off due to the pilot not arriving on time.

Flight was great. On time. Pleasant crew and responsible passengers. My only disappointment was that there was no coffee or tea offered. It was a short flight but a coffee would have been appreciated for what the price of tickets are now.

Terrible. Quality has gone down significantly. Plane was delayed. No instructions from the staff. Will try to avoid in the future!

The flight left unexpectedly early. Although I checked in at the gate, the crew made no attempt to contact me to inform me that what had been a delayed flight was now departing before the scheduled departure time. No announcement on the PA, no phone call. When I checked back at the gate for the delay status just before the scheduled departure time, I was told the doors were already locked and the flight had left.

Late boarding, had to check the bag even though there was space on the flight and I was I row 7

Our seats were moved for no reason. The plane was old and wifi and tv were slow. The flight was delayed over an hour for a paperwork issue. Only bright spot was the flight attendants good service.

Unacceptable pre-boarding ticket issues. Paid for and reserved Mint seat approximately a month in advance. Checked in to flight in Mint seat 24 hours before flight. Shortly before flight, was bumped out of Mint entirely, even though other Mint seats were still available and for sale. Was told it was "operational", however seats were still available/being sold. Got to gate and they could not explain it, but the gate agent was able to put me back into Mint (however to a different seat). Nothing proactive done by Jetblue, I would have been bumped had I not arrived at gate early enough to have a helpful gate agent rectify. No explanations from Jetblue.

The crew did not ensure the Evermore seats had their carry on space available. When my family and I boarded, we saw people putting their carry on suitcases in the overhead spaces above our seats and then proceed to the rear part of the plane. This resulted in us having to check our bags and being late to our meetings/events.

Crew was friendly. Free headphones would be nice. Free new movies would be better.

Diana at the gate was unhelpful which was fine, but she was also rude which I did not appreciate at all.

Multiple delays, poor communication, dismissive staff, chaotic boarding, broken seat back entertainment. Not really much to like.

The crew was friendly and helpful. The entertainment system in my row did not work for movies and TV shows and the Direct TV cut off in parts and stopped showing the baseball playoff game.

Staff announced flight was delayed. Then after passengers took the extra time to get food etc, announced it was on time. Not enough overhead space for a full flight Seats were super small and crammed. Crew welcomed us aboard to another "on time gate departure” only to sit on the tarmac for two hours. They made 2 announcements as to why that no one could understand. NO ENTERTAINMENT- food was a bag of old pretzrks. After landing, sat on the tarmac for another 20 minutes “looking for a parking spot”. I never fly American due to past poor performance. I had to that day due to departure time. American never fails to disappoint.

There was no clear update on the flight until last minute and made it an hour delay. No clear flight aircraft or incoming flight which we will be boarding. We would plan accordingly for our connecting flight. This is one one the worst service, I also had to buy an another ticket with different ai carrier. American airline was not letting me plan my trip, made us just waiting. Not a good service at all.

The flight attendance were very pleasant and funny. They made boarding and the flight very pleasant. Just wish the seats cushions had more comfort. Very flat and hard.

American Airlines put the food on the wrong plane which had already taken off by the time we took off so we had no food on the plane.

Flying on this airline is nothing short of a full blown circus clown show. On a recent return from my mother’s funeral, my only available choice from IND to PWM was American, which I hesitantly booked as I rarely fly them for many of the following reasons and never will again. I was booked IND-PHL-PWM totaling about six hours. The flight was cancelled due to NE weather. They rebooked me on a two stop flight IND-DFW (Yes DALLAS)-PHL-PWM, still all on the same day. After arriving in DFW, they continually delayed the DFW-PHL flight due to maintenance issues on the arriving flight. Finally it was delayed to the point that my PHL-PWM connection was no longer possible. They then rebooked me thru LGA with the short flight the NEXT DAY to PWM and offered to put me up for the night in NYC (or so I assumed). The flight DFW-LGA was then delayed so much that I asked to be put in an earlier flight with a lessor delay. Throughout this day chats with their AI assistant were useless as were subsequent chats supposedly with a real person(?). Only one customer service agent in DFW was actually helpful and appeared to care. Upon arrival at LGA post midnight, they issued me car and hotel vouchers in Trenton NEW JERSEY at a very old Howard Johnsons ONE HALF HOUR from LGA. The hotel was an $85, 1.5 rated hotel in a very sketchy area of NJ that I would have never voluntarily booked. As I prepared to catch the car back to LGA the next morning I received a text that my flight was cancelled. TWICE IN TWO DAYS. I went to LGA hoping to have AA book me on an earlier Delta flight. The full service line was at least 200 people deep, so I tried to reach a real person agent by phone. After 1/2 hours on hold I gave up and waited for my later LGA-PWM flight. It actually started boarding on-time, but only shortly after announced a maintenance hold. We were told it was nothing serious, just an adjustment to the Captains seat. Only one update was given while we waited 1.5+ hours for a “SEAT ADJUSTMENT”. Can’t forget to mention that on all of these planes the WiFi only worked on two. During that time at least three others flights in my area announced that they were overbooked and were taking volunteers before bumping people. Another flight to ORD announced a gate change and less than five minutes after announced that they were really not changing and announced for everyone to return to that gate. Can’t forget to mention that on all of these planes the WiFi only worked on two.🤡🤡

Flying on this airline is nothing short of a full blown circus clown show. It is so mismanaged it should not be in business as there is no way it can be safe as badly as it is managed. It is 100% about money and customers be damned. On a recent return from my mother’s funeral, my only available choice from IND to PWM was American, which I hesitantly booked as I rarely fly them for many of the following reasons and never will again. I was booked IND-PHL-PWM totaling about six hours. The flight was cancelled due to NE weather. They rebooked me on a two stop flight IND-DFW (Yes DALLAS)-PHL-PWM, still all on the same day. After arriving in DFW, they continually delayed the DFW-PHL flight due to maintenance issues on the arriving flight. Finally it was delayed to the point that my PHL-PWM connection was no longer possible. They then rebooked me thru LGA with the short flight the NEXT DAY to PWM and offered to put me up for the night in NYC (or so I assumed). The flight DFW-LGA was then delayed so much that I asked to be put in an earlier flight with a lessor delay. Throughout this day chats with their AI assistant were useless as were subsequent chats supposedly with a real person(?). Only one customer service agent in DFW was actually helpful and appeared to care. Upon arrival at LGA post midnight, they issued me car and hotel vouchers in Trenton NEW JERSEY at a very old Howard Johnsons ONE HALF HOUR from LGA. The hotel was an $85, 1.5 rated hotel in a very sketchy area of NJ that I would have never voluntarily booked. As I prepared to catch the car back to LGA the next morning I received a text that my flight was cancelled. TWICE IN TWO DAYS. I went to LGA hoping to have AA book me on an earlier Delta flight. The full service line was at least 200 people deep, so I tried to reach a real person agent by phone. After 1/2 hours on hold I gave up and waited for my later LGA-PWM flight. It actually started boarding on-time, but only shortly after announced a maintenance hold. We were told it was nothing serious, just an adjustment to the Captains seat. Only one update was given while we waited 1.5+ hours for a “SEAT ADJUSTMENT”. During that time at least three others flights in my area announced that they were overbooked and were taking volunteers before bumping people. Another flight to ORD announced a gate change and less than five minutes after announced that they were really not changing and announced for everyone to return to that gate. Can’t forget to mention that on all of these planes the WiFi only worked on two.🤡🤡

IT issues created a mess had you change my flight and your system never changed it

The ground closures and flight delays were unwelcome. I think the captain did what he could to manage expectations for the delays, but the stress level increasing in the cabin was palpable with every announcement. It may be obvious to those who fly frequently, but if the ground is closed for us to get to a gate, it's also closed for connecting flights to leave. Other passengers were so stressed they were rude. A bit further explanation could have helped.

I’ve been on 8 flights with American Airlines in the last 2 months and 4 have been delayed.

Passenger was too loud for the entire flight crew not once ask them to tame it …. Many passengers are uncomfortable including having headaches

More options for your flight to Caribbean Islands

Complete your trip to Caribbean Islands with a hotel stay or car rental