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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 Cana1 stop$442
Santo Domingo
Santo Domingo1 stop$359
Montego Bay
Montego Bay1 stop$494
Oranjestad
Oranjestad1 stop$483
Nassau
Nassau1 stop$282
Kingston
Kingston1 stop$585
Simpson Bay
Simpson Bay1 stop$436
Providenciales
Providenciales1 stop$457
Port of Spain
Port of Spain2 stops$739
Bridgetown
Bridgetown1 stop$701
George Town
George Town2 stops$482
Willemstad
Willemstad2 stops$695
Aguadilla
Aguadilla1 stop$289
Puerto Plata
Puerto Plata1 stop$805
St. John's
St. John's1 stop$943
Punta Cana
Punta Cana1 stop$442
Santo Domingo
Santo Domingo1 stop$359
Montego Bay
Montego Bay1 stop$494
Oranjestad
Oranjestad1 stop$483
Nassau
Nassau1 stop$282
Kingston
Kingston1 stop$585
Simpson Bay
Simpson Bay1 stop$436
Providenciales
Providenciales1 stop$457
Port of Spain
Port of Spain2 stops$739
Bridgetown
Bridgetown1 stop$701
George Town
George Town2 stops$482
Willemstad
Willemstad2 stops$695
Aguadilla
Aguadilla1 stop$289
Puerto Plata
Puerto Plata1 stop$805
St. John's
St. John's1 stop$943
Booking Insights

Price, demand and travel trends for Indianapolis to Caribbean Islands flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights with more confidence.

Are flights from Indianapolis to Caribbean Islands cheaper or more expensive than last year?

Fares from Indianapolis to Caribbean Islands are about 7% higher than they were in November last year, averaging $646 round-trip.

What's the cheapest month to fly from Indianapolis to Caribbean Islands?

January is typically the cheapest month to fly from Indianapolis to Caribbean Islands, with round-trip fares averaging $526. December and June are usually the most expensive, averaging $764 and $694, respectively.

How do fares from Indianapolis to Caribbean Islands vary by day of the week?

On average, Tuesday is the cheapest day to fly from Indianapolis to Caribbean Islands and Saturday is the most expensive. Looking at the past 12 months of KAYAK data, it's 27% more expensive to fly on a Saturday compared to Tuesday.

What's the best time of day to fly from Indianapolis to Caribbean Islands?

It's cheapest to fly to Caribbean Islands in the evening with average prices of $583. The morning is the most expensive time to fly, with average prices of $698.

What's the best time to book a flight from Indianapolis to Caribbean Islands?

Book your flights 24 weeks before your trip. KAYAK data collected over the past 12 months shows that booking in this window can save you around 14% compared to booking at the last minute (within 2 weeks of departure).

Key details for Indianapolis to Caribbean Islands flights

Low season

September
Beat the crowds with an average 30% drop in travelers.
The most popular month to fly with an average 18% increase in travelers.

Your Indianapolis to Caribbean Islands flight questions, answered

Find helpful answers about this route, including flight times, airports, airlines and booking tips.

  • How much should I budget for a flight from Indianapolis to Caribbean Islands?

    Over the past 12 months, round-trip fares from Indianapolis to Caribbean Islands have typically cost between $493 and $878.

  • Which airlines fly nonstop from Indianapolis to Caribbean Islands?

    Based on the flight schedule for the next 3 months, just one airline regularly flies nonstop from Indianapolis to Caribbean Islands: American Airlines.

  • Is it cheaper to fly with a layover from Indianapolis to Caribbean Islands?

    Yes, nonstop flights from Indianapolis to Caribbean Islands average $625 over the past 12 months, but flights with a layover can cost less. The most affordable connecting airports are:

    • Washington, D.C. Reagan-National (DCA) (avg. price $503)
    • Chicago O'Hare Intl (ORD) (avg. price $516)
    • Houston George Bush Intcntl (IAH) (avg. price $591)

  • How long is a flight from Indianapolis to Caribbean Islands?

    Nonstop flights from Indianapolis to Caribbean Islands take 4h 14m on average.

  • Which cabin classes are available from Indianapolis to Caribbean Islands?

    On flights from Indianapolis to Caribbean Islands you can book Economy Class, Business Class or First Class.

  • What are some popular landmarks around Caribbean Islands?

    Caribbean Islands is home to many popular sights. KAYAK travelers' favorites include:

    • Viejo San Juan
    • Palm Beach
    • Eagle Beach
    • Puerto Rico Convention Center

  • What are the earliest and latest flights from Indianapolis to Caribbean Islands?

    The earliest nonstop flight from Indianapolis to Caribbean Islands departs at 7:00 am and the latest leaves at 7:00 am. Nonstop flights take about 4h 14m.

Your guide to booking Indianapolis to Caribbean Islands flights

Get tips on when to book, when to fly and what to know before your trip.
  • If you can plan ahead, the sweet spot for booking your flight is 24 weeks before your trip. KAYAK data shows fares in this window are around 14% lower than last-minute bookings (made within 2 weeks of departure). Not ready to commit? Set a Price Alert and we'll let you know when prices change.
  • Flexible with your dates? Fly in January to save some money. It's typically the cheapest month on this route, while flights in December will cost you the most.
  • Fly out on a Tuesday to get the cheapest fares. Avoid Saturday flights, which are about 27% more expensive.
  • Start your trip in Punta Cana, the most popular destination in Caribbean Islands. From there, it's easy to continue on to other popular spots such as San Juan, Oranjestad and Nassau.

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.
8.0
SouthwestOverall score based on 4222 reviews
8.0Comfort
8.1Boarding
8.6Crew
7.5Entertainment
7.0Food
Airline reviews

Terrible, decided to delay our flight since another flight require a flight captain

2.0 MediocreChih Hsuan, Nov 2026
Read more Southwest reviews

Terrible, decided to delay our flight since another flight require a flight captain

staff and crew were great but the flight delays for the last few flights are insane. After a long day of work and you will get a notification of flights delay is not the message we want to see. And for some reason it keeps happening often this year.

I love southwest. I can not wait until all the planes convert to the upgraded planes. I love the charging option and the newer seats. Thank you from a very loyal Southwest customer.

My return flight was much better than the flight there! I paid for seat to Veagas but not the return. Thankgoodness they assigned me a seat with additional leg room as I have back and leg problems. I really appreciate it. With the flight already being super expensive due to gas prices and having to pay for bags (now) I needed to save some money.

My first flight from LGA to STL was not good. They didn't do service until over halfway through the flight, the internet didn't really work, and the crew all seemed like they didn't want to be there.

We were stressed about landing as our connecting flight was about to start boarding, being unfamiliar with the airport or where the gates were. We exited the plane to discover we were at the gate we needed. We would be getting back on the same plane but nobody told us we could have just stayed onboard. My wife and I were seated on aisle seats across from each other. We asked if there was a way we could sit together. Once we were at cruising altitude they let us move to an unoccupied row so that was nice.

It’s Southwest. The seats are small, the snacks are meh, it’s $50 to check a bag. It’s exactly fine. Could have been better. Could have been worse. It’s not Spirit

They delayed my flight all day but didn't try to reschedule me until all other options were gone. Ended up on a red eye. Not happy. Lesson learned, don't book the last flight from SJC to RDU.

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

As an Elevance employee, don't we get priority boarding? Also, I boarded zone 5 and could not get normal carry on in luggage space. There were many Delta employees on the flight and their bags, which were large and could only fit two bags per compartment, got preference over customers so I had to check my bag.

Everything went smoothly, WiFi connection was strong. Time to upgrade the regional planes, we are all on top of each other. No room to comfortably do anything.

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

It is completely insane to me that first class does not include WiFi. Also does not include lounge access. Port for phone charging did not work. The crew was absolutely lovely, and the food was excellent.

I appreciate how quickly and kindly the people at the gate at DCA accommodated several of us who wanted to switch from the 6pm flight to the 5pm flight at the last minute. The flight crew was helpful to us too (dealing with luggage).

Very uncomfortable and cramped seats. Everything else was okay, the crew members were nice but nothing was exceptional.

Check in went smoothly. Flight attendant who was assigned my area barely paid any attention to me! She acted as though she was extremely busy and flustered. Maybe she was new?! I told her to change the language on my screen, she said she’d come back to help me but never did so I was able to solve the problem on my own. She came back and said she’d made adjustments on her end. Highly doubt it because I found the setting to change the language! Also, I noticed everyone was eating before we landed so I pushed my help button and she never came so I got up to find her to ask her if I can have breakfast. She said they are not serving breakfast but I can have a sandwich. Yes, that was her response as I saw everyone eating breakfast!!!

United staff were very communicative, the new starlink Wifi is amazing as I was able to work easily.

Starlink internet made the flight time shrink and I was able to work.

Tiny seat made for midgets. You can’t put a normal size human in such a tiny seat for 8 god damn hours! Hot plane, no air. Lost bags at Rome airport for 8 hours, lucky to have found them. Horrible flying experience, United Airlines should be embarrassed!

The issue is the flight is delayed, which causes me Missing the connecting flight by 3 mins. Remember the connecting flight is a US codeshare flight so UA should be able to inform the operating airline about the delay.

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.

Flight was canceled after 5 hours of delays sitting at the airport

I’m still in Boston and I was supposed to be home yesterday at 2:30pm

Fort Lauderdale doesn't have Priority Security line so why was such option available for purchase? I need a refund back

1/2 full flight, nice and comfy flight. On time, good service

Both ways the people in the rear section of the plane were forced to check their carry on bags. I would understand this if the size and number of bags were not limited, but I do not understand why there is not room for one small overhead bag per person, even if the flight is full. I could watch the baggage handlers loading the extra luggage from my window and I’m pretty sure mine wouldn’t have survived undamaged, even though it is new and sturdy.

You sent me a confirmation yesterday for a flight reservation today that I never made. What is going on?????

Entertainment, clean plane and funny pilot over the intercom was excellent… however, gate agent was rude and was probably a Spirit employee before they went bankrupt… there were 3 flight attendants - 2 of them didn’t want to be there the other one was kind and nice… I want you to recognize how you have to compete with Delta or South West airlines or even American Airlines which would choose over you at any given day from here on out. Please treat people respectfully. If you hate working in this industry - go and work somewhere else. The flight was very empty and it shouldn’t be hard to crack a smile once in a while. Very disappointing… I remember flying Jet Blue back in the day from Dulles IAD to LAX and you guys were super cool and fancy and made flying fun again - truly elevated the experience. Don’t become the next most hated airline… you can do better . I want you to succeed…

Free wifi was almost impossible to get, kept dropping the connection

Not good - we boarded and taxied for an hour before they told us there were technical issues with the plane. They told us we were going to need to deplane, parked back at the gate but then didn’t tell us we didn’t have to anymore. There was just a lot of uncertainties with poor communication.

3.5 hour delay because of “mundane” mx issue. Aircraft had to be towed 3 times.

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