$108 Find Cheap Flights from Indianapolis to Caribbean Islands - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Indianapolis to Caribbean Islands departing on 11/17. 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.
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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$434
Santo Domingo
Santo Domingo1 stop$522
Montego Bay
Montego Bay1 stop$387
Oranjestad
Oranjestad1 stop$473
Nassau
Nassau1 stop$374
Kingston
Kingston1 stop$734
Simpson Bay
Simpson Bay1 stop$439
Providenciales
Providenciales1 stop$457
Port of Spain
Port of Spain1 stop$587
Bridgetown
Bridgetown1 stop$412
George Town
George Town1 stop$412
Willemstad
Willemstad2 stops$645
Aguadilla
Aguadilla1 stop$278
St. John's
St. John's1 stop$758
Puerto Plata
Puerto Plata1 stop$660
Punta Cana
Punta Cana2 stops$434
Santo Domingo
Santo Domingo1 stop$522
Montego Bay
Montego Bay1 stop$387
Oranjestad
Oranjestad1 stop$473
Nassau
Nassau1 stop$374
Kingston
Kingston1 stop$734
Simpson Bay
Simpson Bay1 stop$439
Providenciales
Providenciales1 stop$457
Port of Spain
Port of Spain1 stop$587
Bridgetown
Bridgetown1 stop$412
George Town
George Town1 stop$412
Willemstad
Willemstad2 stops$645
Aguadilla
Aguadilla1 stop$278
St. John's
St. John's1 stop$758
Puerto Plata
Puerto Plata1 stop$660
Booking Insights

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?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to Caribbean Islands from Indianapolis found in the last 5 days was to San Juan, at $612 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 $645.

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

The average price for all round-trip flights from Indianapolis to Caribbean Islands depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

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?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $402, prices are generally cheapest when you fly direct.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Indianapolis to Caribbean Islands, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Indianapolis to Caribbean Islands is January, when tickets cost $535 (return) on average. On the other hand, the most expensive months are June and December, when the average cost of round-trip tickets is $694 and $684 respectively.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Indianapolis to Caribbean Islands, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

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 21% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 10 weeks before departure.

Good to know

Low season

August

Cheapest flight

$108
Best time to beat the crowds but there is an average 1% increase in price.
Most popular time to fly with an average 10% increase in price.
Flight from Indianapolis to San Juan

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

 
See real verified KAYAK customer reviews for airlines flying from Indianapolis to Caribbean Islands. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
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.
8.0
SouthwestOverall score based on 4219 reviews
8.0Comfort
8.6Crew
7.5Entertainment
7.0Food
8.1Boarding
Airline reviews

Seated at front bulkhead for a smidge extra leg room away from home and on flight back home. Away crew was very proactive about assuring our carryons had space close behind us (because no seat in front of us our personal items had to be in a small bin overhead). They actively required passengers place overhead luggage on its side so more items could fit in bins. Home crew made no such efforts. I had to struggle back rows to get overhead bags upon landing, no crew help then either, and some disgruntled passengers as I and others retrieved our bags. There was a system that worked pretty well. The home bound crew just didn't feel like working.

4.0 OkayMather, Aug 2026
Read more Southwest reviews

Seated at front bulkhead for a smidge extra leg room away from home and on flight back home. Away crew was very proactive about assuring our carryons had space close behind us (because no seat in front of us our personal items had to be in a small bin overhead). They actively required passengers place overhead luggage on its side so more items could fit in bins. Home crew made no such efforts. I had to struggle back rows to get overhead bags upon landing, no crew help then either, and some disgruntled passengers as I and others retrieved our bags. There was a system that worked pretty well. The home bound crew just didn't feel like working.

Southwest has inacted unfriendly customer policies like other airlines. Watch the fine print very carefully if you are having to alter flight arrangements. Rules are now complicated and very stilted to travelers sacrificing travel funds (unlike before where the simple, straight forward flight change policy was worth the extra premium for ticket price.) On the positive side, SW Flight crews are still wonderfully helpful.

Flight left on time and was early landing. Seats not comfortable and not enough space…

Flight left on time. Seat spacing is way too small…

It would have been better if the flight was on time

Fairly good - the seats seemed more comfortable on this flight. The staff out of Detroit were quite friendly. But they directed us to the wrong carousel for luggage. :(

Just crazy with times being pushed and pushed and pushed and gate crew at Philly super rude and unprofessional with many under stress with delays.

I liked the new boarding process. I thought the buyup options (legroom, early boarding) to be easy to request and reasonably priced. All the Southwest team from gate to in-flight were so nice.

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

Flight was delayed and we were on the runway after landing for 30 mins

The plane is old. There was water dripping fown from the air cooling system. The toilets were mot that clean

We were delayed so pilots can rest and had no WiFi the whole trip. First class seats are small compared to other planes

The experience was bad. Flight was delayed to handle maintenance (understandable) but still there was some dew forming and dropping as droplets on few seats. Internet at best was allowing some browsing but at a snail pace.

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

Flight did not have wifi service. It was experiencing technical difficulties. Definitely and old plane that needs updating.

Very Poor. Significant delays getting to Chicago and then very poor communication on delays in Chicago to Cleveland. We could have rented a car and driven there faster than the delays ended up being.

A little more friendliness from that crew of the day.

The app logs you out right when you are boarding requiring all passwords and reservation number for the flight. Super annoying

The pre-order only approach for fresh food is really challenging

This flight has a history of leaving late, however, I was pleasantly surprised that it was not delayed this day. The flight went smooth, except I was in a window seat and the wall and my feet were freezing. I found it difficult to sleep due to being so cold, I also was using 2 provided UAL blankets and could not get my feet warm. This was annoying, but I still made it there on time and safe.

Staff didn't seem confident about the ingredients in my lactose intolerance meal

the seat has a problem. the back had a hole.

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.

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

The Mario was so helpful and provided amazing customer service however l have being waiting for a callback for almost a week now and have not heard anything further after l informed them l wanted to change my date of traveling because of my hospital appointment even send them proof and l was unable to use manag your booking on their website is a bit frustrating and l would appreciate an update on My request as soon as possible. And have called them times without numbers no response

There is no room, no gluten free options, or any free internet/entertainment. You have to bring your own tablet or smartphone because there are no screens.

April was the flight attendant in first class and was the most pleasant, cordial and efficient person I have seen on a flight in years. Good example of the type of people AA should hire to increase customer satisfacdtion.

Excellent accommodating crew at gate and on board. Baggage claim and gate checking were flawless.

My screen didn’t work, my seat didn’t recline, the flight attendant was rude and completely dismissive, the airplane was freezing, the seats are way old, slanted and uncomfortable. I payed for a full ticket and got a horrific experience, with a flight attendant who dismissed me even though I was calm respectful and polite.

Very poor help no one answering a question regarding seating. Very rude staff. They don’t care, as if it’s not part of their job. Flight was delayed for no good reason and no apologies given.

It was my worse flying experience. It was my first time and last time flying with Jet Blue.

The wifi didn't work and I needed to do some work. This was a business trip.

It was my first time in Jetblue flight in 10+ years(?) and the experience was horrible. You were better before. There were ATC delays sitting/waiting in the tarmac for 2 hours, I understand that this isn't Jetblue's problem but how the matter was handled poorly is. Cabin was so warm and hot couldn't get it to cool down for the entire waiting period worse, even during cruise flight. Start, the passengers were spoken to and treated like a little children with no respect. Constant/multiple annoying tone/voice PA announcements of mentioning "... only big/large suitcases are for the bin and small ones need to be placed under the seat, etc,..." I see that flight was delayed and crew were trying to get the plane ready to board as soon as they can but the way they presented was lack of better word, condesending and scolding tone to cattle. It was definite unpleasant, unwelcoming flight experience I have ever had with Jetblue. Whatever happen to smiles and fun employees , pleasant/helpful gate agents, flight attendants, crews, where have they gone? It was dissapointing flight experience overall from everyone. Sorry for the direct transparency.

Flight was cancelled as JetBlue could not find a pilot. Communication was poor and they did nothing for stranded passengers. Flight they rebooked us on was 4 days out.

JetBlue cancelled the flight. We had to rebook on another airline.

JetBlue cancelled the flight along with hundreds of others, for no apparent reason. no recourse, no rebooking options. never booking with them again

Jet Blue cancelled my flight after I had boarded. They attempted to rebook me for a new flight two days later. I was able to rebook with a different airline, but not until the next morning. As such, I was forced to get an expensive hotel and missed important work meetings Monday morning. I am very disappointed with the customer service and will be pursuing full reimbursement for my hotel cost.

You did a great job rescheduling my cancelled flight. However, you made me pay for two seats for $118 even though the seats on the original flight were free. I think that was a very unfair thing to do.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports