$115 Find Cheap Flights from Indianapolis to Caribbean - 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 departing on 10/5. 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

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana1 stop$438
Santo Domingo
Santo Domingo1 stop$582
Montego Bay
Montego Bay1 stop$450
Oranjestad
Oranjestad1 stop$451
Nassau
Nassau1 stop$373
Kingston
Kingston1 stop$541
Simpson Bay
Simpson Bay1 stop$419
Providenciales
Providenciales1 stop$423
Port of Spain
Port of Spain1 stop$538
Bridgetown
Bridgetown1 stop$416
George Town
George Town1 stop$401
Willemstad
Willemstad1 stop$395
Aguadilla
Aguadilla1 stop$316
St. John's
St. John's1 stop$758
Puerto Plata
Puerto Plata1 stop$660
Punta Cana
Punta Cana1 stop$438
Santo Domingo
Santo Domingo1 stop$582
Montego Bay
Montego Bay1 stop$450
Oranjestad
Oranjestad1 stop$451
Nassau
Nassau1 stop$373
Kingston
Kingston1 stop$541
Simpson Bay
Simpson Bay1 stop$419
Providenciales
Providenciales1 stop$423
Port of Spain
Port of Spain1 stop$538
Bridgetown
Bridgetown1 stop$416
George Town
George Town1 stop$401
Willemstad
Willemstad1 stop$395
Aguadilla
Aguadilla1 stop$316
St. John's
St. John's1 stop$758
Puerto Plata
Puerto Plata1 stop$660

Book Cheap Indianapolis 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 Indianapolis 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 Indianapolis to Caribbean

Sat, Sep 19 - Fri, Sep 25
Frontier Logo
6:27 pm - 1:52 amIND  Indianapolis-SJU San Juan Luis Munoz Marin Intl
7h 25m1 stop Orlando
Frontier Logo
2:57 am - 10:25 amSJU  San Juan Luis Munoz Marin Intl-IND Indianapolis
7h 28m1 stop Orlando
$182Frontier
Mon, Oct 12 - Wed, Oct 28
Multiple Airlines Logo
12:39 pm - 11:38 pmIND  Indianapolis-SJU San Juan Luis Munoz Marin Intl
34h 59m2 stops Atlanta Hartsfield-Jackson Fort Lauderdale
Multiple Airlines Logo
5:12 pm - 8:39 pmSJU  San Juan Luis Munoz Marin Intl-IND Indianapolis
27h 27m1 stop Fort Lauderdale
$231Multiple Airlines
Mon, Oct 12 - Wed, Oct 28
Multiple Airlines Logo
12:39 pm - 12:16 amIND  Indianapolis-SJU San Juan Luis Munoz Marin Intl
35h 37m2 stops Atlanta Hartsfield-Jackson Miami
Multiple Airlines Logo
5:12 pm - 8:39 pmSJU  San Juan Luis Munoz Marin Intl-IND Indianapolis
27h 27m1 stop Fort Lauderdale
$233Multiple Airlines
Wed, Sep 16 - Tue, Sep 22
Frontier Logo
7:48 pm - 11:58 pmIND  Indianapolis-SJU San Juan Luis Munoz Marin Intl
28h 10m2 stops Atlanta Hartsfield-Jackson Tampa
Frontier Logo
6:42 pm - 10:25 amSJU  San Juan Luis Munoz Marin Intl-IND Indianapolis
15h 43m1 stop Orlando
$266Frontier
Mon, Dec 14 - Thu, Dec 24
American Airlines Logo
9:39 am - 4:58 pmIND  Indianapolis-STT Saint Thomas Island Cyril E King
6h 19m1 stop Miami
American Airlines Logo
3:01 pm - 10:29 pmSTT  Saint Thomas Island Cyril E King-IND Indianapolis
8h 28m1 stop New York John F Kennedy Intl
$320American Airlines
Sun, Oct 11 - Thu, Oct 15
American Airlines Logo
7:58 pm - 2:55 pmIND  Indianapolis-STT Saint Thomas Island Cyril E King
18h 57m2 stops Charlotte Douglas Miami
American Airlines Logo
3:46 pm - 9:28 amSTT  Saint Thomas Island Cyril E King-IND Indianapolis
17h 42m2 stops Miami Charlotte Douglas
$320American Airlines
Mon, Sep 28 - Mon, Sep 28
United Airlines Logo
7:07 am - 2:44 pmIND  Indianapolis-SJU San Juan Luis Munoz Marin Intl
7h 37m1 stop Chicago O'Hare Intl
United Airlines Logo
1:00 am - 12:42 pmSJU  San Juan Luis Munoz Marin Intl-IND Indianapolis
11h 42m2 stops Newark Chicago O'Hare Intl
$361United Airlines
Sat, Oct 17 - Fri, Oct 23
United Airlines Logo
1:38 pm - 11:50 pmIND  Indianapolis-SJU San Juan Luis Munoz Marin Intl
10h 12m2 stops Chicago O'Hare Intl Newark
United Airlines Logo
1:00 am - 10:56 amSJU  San Juan Luis Munoz Marin Intl-IND Indianapolis
9h 56m2 stops Newark Chicago O'Hare Intl
$366United Airlines
Sun, Nov 8 - Sat, Nov 14
Southwest Logo
2:25 pm - 12:55 amIND  Indianapolis-SJU San Juan Luis Munoz Marin Intl
9h 30m2 stops Atlanta Hartsfield-Jackson Orlando
Southwest Logo
5:00 pm - 11:25 pmSJU  San Juan Luis Munoz Marin Intl-IND Indianapolis
7h 25m1 stop Orlando
$366Southwest
Tue, Nov 3 - Fri, Nov 6
Southwest Logo
2:10 pm - 12:45 amIND  Indianapolis-SJU San Juan Luis Munoz Marin Intl
9h 35m2 stops Baltimore/Washington Orlando
Southwest Logo
5:35 am - 3:35 pmSJU  San Juan Luis Munoz Marin Intl-IND Indianapolis
11h 00m2 stops Orlando Nashville Intl
$366Southwest
Booking Insights

KAYAK's insights & trends for Indianapolis to Caribbean flights

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

What is the cheapest Indianapolis to Caribbean flight route?

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

The cheapest ticket to Caribbean 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?

The average price for all round-trip flights from Indianapolis to Caribbean 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 is generally in the morning, when round-trip flights cost $552 on average. The most expensive time of day to fly to Caribbean 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?

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 $550, prices are generally cheapest when you fly direct.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Indianapolis to Caribbean, 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 is September, when tickets cost $486 (return) on average. On the other hand, the most expensive months are June and December, when the average cost of round-trip tickets is $669 and $665 respectively.

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

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, 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, you should book around 2 weeks before departure, which saves you about 22% 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

$115
Best time to beat the crowds with an average 1% drop in price.
Most popular time to fly with an average 9% increase in price.
Flight from Indianapolis to San Juan

FAQs - booking Caribbean flights

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

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Indianapolis 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 Indianapolis 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 Indianapolis 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 Indianapolis 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 Indianapolis 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 5 airlines serving from Indianapolis to Caribbean

 
Need help choosing which airline to fly with from Indianapolis 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.
8.0
SouthwestOverall score based on 4218 reviews
7.5Entertainment
7.0Food
8.0Comfort
8.1Boarding
8.6Crew
Airline reviews

Exceptional. The gate crew responded quickly and got me onto this earlier flight as the final passenger, saving me more than four hours of wait time for my reserved flight.

10.0 ExcellentAnonymous, Aug 2026
Read more Southwest reviews

Exceptional. The gate crew responded quickly and got me onto this earlier flight as the final passenger, saving me more than four hours of wait time for my reserved flight.

The flight was delayed due to earlier issues at other airports. The crew was excellent & made it a good trip.

Boarding process of asking for volunteers to check bags goes against the system you had before with 2 bags checked free. This process is more of a guilt trip than a caring attitude toward the customer. In addition bag-size scrutiny has increased which also slows down the process of boarding. My wife said she will not fly on your airline again unless there is no other option.

Eveeyrime I fly they are begging for bags due to cabin overhead space. What they should so ia take the bags that are clearly too big to fit wheels first on their side. And those of us who give up the bag should really get their bags first. When boarding, nobody wants stupid jokes about how hot it is on board. Give us some cool air. Im usually sick from the heat by the time we take off.

No wifi, seems to be very common with Southwest currently. Everything else was normal.

Poor customer service, no accommodation for passengers when the flight was delayed over 5 hours.

Friendly crew kept coming by to make sure all was ok, provide additional refreshments, etc.

It was good. Last flight was delayed but I always say that is in God's plan

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

the flight got cancelled - few hours before the departure time - no time to change

This a short easy flight. No food or drink but that was not an issue since we were only in the air for 35 minutes.

The meal tray was not usable it was completely uneven

My experience with Delta started with my luggage being found ripped open with items missing. The baggage office told me to bring the bag, and I wanted them to see how I found it. The agent refused, so I carried my bag into the office myself. The agent was nice enough to fix the zipper and gave me a red card with a number to call. I followed the steps; first one department, then the baggage department took over. This took more than two hours on the phone. The return flight was okay. The flight lead was checking her meals and then asked if we wanted anything before departure. However, throughout the flight, I had to ask for things because she was reading her book;which I have no issue with if she had been more attentive. At the end of the flight, the pilot appeared annoyed with the flight lead for not following his instructions regarding a meal he had requested; a chicken sandwichand said, "I asked for that for the flight." On the positive side, my work event in Vegas went well, and now I'm home relaxing.

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 was a good experience, unfortunately my checked baggages were come late and not arrived on time.

Very stressful to locate United Airline boarding area, delayed flight, changing boarding area again to another location with all tiredness 😩. But flying was fine.

Staff and flight attendants were very polite. Flight was smooth. My seat on the plane was a bit broken so it would not stay in upright position but it was fine for the most part.

Flight staff and all was fine. Food always sucks on planes so nothing new.

The flight crew were very helpful. The seats were very close together. There was barely room to sit without touching the person next to you.

I’m an EP on AA every year for more than a decade but this was a very pleasant and surprising experience. Clean and sizable plane for HOU to CHI. 5 row first class. And excellent food in first class the steak option was really good. Your flight attendants even better. Seat 5A

It was hot and not as comfortable as the flight to Chicago. Must have been a different plane that needs to be worked on or replaced.

My flight was delayed so bad i missed u it so i just said never mind

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.

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.

Delayed 6 times. Eventually rebooked and missed a whole day of my vacation. Hot mess

Unfriendly gate staff and significant delay once we were on the plane.

I know Frontier is a “no-frills” airline. I understand the concept. However, I jumped on some tickets for our family vacation, expecting to play a bit of a game to figure out the family bags and not over spend. In the end, I got the short end of this deal by far. 1. I did not expect them to charge the baggage fee for each direction. It makes the fee look high-ish at a glance, but reasonable. Then when you get to checkout and realize you have to pay it twice to come home with your luggage, it becomes ridiculous. 2. The low checked bag weight limit. I am used to packing a 50lb bag with my preferred airline. Frontier’s artificially low 40lb limit more quickly triggers the extra weight fee, which almost DOUBLES the price of the bag if you go over ($79 for the bag/$75 for the next 10 lbs) 3. The fee for a carry-on bag is the same as a checked bag but with a lower size and weight limit. Make it make sense! 4. The seats are terrible. My 2.5 hour flight almost had me losing my mind. I’m 6’3” and my femurs barely fit in the space provided. My knees had to wiggle just right to jam into the crack next to the armrest of the seat in front of me. The cushioning was thin and inadequate. I am tall but I’m not a freak. These seats are unacceptable. 5. I overheard the woman next to me speaking with the gate agent about being charged a $25 fee for not checking in online - she checked in at the airport counter when she arrived. That’s ridiculous. She was old and in a wheelchair. She had a paper boarding pass, and was obviously not tech savvy. She should not be punished for that. 6. They do not have good placement in the terminals. It was always out on the end or down on a subfloor, and we had to walk out on the tarmac almost every time. In Denver. Their home airport! 7. Every time I loaded a new page on the website while buying my tickets or my bags, it was constantly trying to upsell me on some esoteric bundle. Like, a pop-up every time. Very annoying. 8. No screens in the boarding area (at least where we were) to confirm you’re in the right place. Just static gate number signs. I am sure these are standard practices for Frontier, and I should have read more about them before I purchased tickets, but as a result of this single round trip, I do not plan to ever use this cut-rate airline again. I would rather pay the normal amount for a ticket and be treated like a customer instead of a mark.

Our flight was delayed 2 hours and when they changed the the time to 1 hour I wasn't alerted and when I checked the gate the plane was still there but they already shut the doors so I had to buy another flight.

Great except upon arrival it took them a long time to open the doors

Frontier feels like a family I Worked for Eastern Airlines back in the day and I felt the family vibe that I had then. Thank you

Terrible. Delayed my family flight for several hours affecting family plans

During the flight I suddenly felt very sick, and no one from the crew even tried to help me or check on my condition. They seemed completely indifferent and showed no concern for my well-being. I was very disappointed by the lack of care and compassion. I hope the airline improves its customer service and trains its crew to respond better when passengers need assistance.

Tiny seats, no entertainment, no amenities, delays, they charge for carry on and their allowed personal item is smaller than in other airlines.

The seats are tiny and they don’t recline. The planes are dirty and very small. You have to pay for carry on and even the personal item that you’re allowed is smaller than with other airlines. Flights are usually delayed and there’s no screens or any amenities or entertainment.

No fault of Frontier staff: plane was very late, reached Orlando at 1 am, took a while to get luggage. Weather, gov financial shutdown impact on TSA, air controllers seemed to have multiple flights backed up. Frontier staff seemed to cope as gracefully as possible. It did reassure me that I and my new hip could adapt to travel challenges. Food/entertainment were irrelevant to my trip.

Everything was on time and smoothly run. All employees appeared happy and enjoying their job. The delay in take-off was unrelated to anything in Frontier’s control. I wish there were a caffeine-fee, sugar free soda drink option besides water. There are multiple zero sugar caffeine free options.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports