$119 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 10/26. 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 72 hours
Punta Cana
Punta Cana1 stop$410
Santo Domingo
Santo Domingo2 stops$552
Montego Bay
Montego Bay1 stop$449
Oranjestad
Oranjestad1 stop$451
Nassau
Nassau1 stop$371
Kingston
Kingston1 stop$615
Simpson Bay
Simpson Bay1 stop$419
Providenciales
Providenciales2 stops$423
Port of Spain
Port of Spain1 stop$553
Bridgetown
Bridgetown1 stop$427
George Town
George Town2 stops$401
Willemstad
Willemstad2 stops$655
Aguadilla
Aguadilla1 stop$331
St. John's
St. John's2 stops$823
Puerto Plata
Puerto Plata1 stop$660
Punta Cana
Punta Cana1 stop$410
Santo Domingo
Santo Domingo2 stops$552
Montego Bay
Montego Bay1 stop$449
Oranjestad
Oranjestad1 stop$451
Nassau
Nassau1 stop$371
Kingston
Kingston1 stop$615
Simpson Bay
Simpson Bay1 stop$419
Providenciales
Providenciales2 stops$423
Port of Spain
Port of Spain1 stop$553
Bridgetown
Bridgetown1 stop$427
George Town
George Town2 stops$401
Willemstad
Willemstad2 stops$655
Aguadilla
Aguadilla1 stop$331
St. John's
St. John's2 stops$823
Puerto Plata
Puerto Plata1 stop$660

Book Cheap Indianapolis to Caribbean Islands 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 Islands 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 Islands

Sat, Oct 17 - Wed, Oct 28
Multiple Airlines Logo
7:22 pm - 11:38 pm
IND
-
SJU
28h 16m
1 stop
Multiple Airlines Logo
5:12 pm - 8:39 pm
SJU
-
IND
27h 27m
1 stop
$239Multiple Airlines
Mon, Oct 26 - Wed, Oct 28
Multiple Airlines Logo
8:30 am - 11:57 pm
IND
-
SJU
15h 27m
1 stop
Multiple Airlines Logo
5:12 pm - 8:39 pm
SJU
-
IND
27h 27m
1 stop
$243Multiple Airlines
Mon, Oct 5 - Fri, Oct 9
Frontier Logo
7:48 pm - 3:17 pm
IND
-
SJU
19h 29m
2 stops
Frontier Logo
5:12 pm - 1:51 pm
SJU
-
IND
20h 39m
1 stop
$265Frontier
Wed, Sep 30 - Fri, Oct 9
Frontier Logo
7:48 pm - 2:13 am
IND
-
SJU
30h 25m
2 stops
Frontier Logo
5:12 pm - 1:51 pm
SJU
-
IND
20h 39m
1 stop
$272Frontier
Sun, Oct 11 - Fri, Oct 16
American Airlines Logo
7:58 pm - 2:55 pm
IND
-
STT
18h 57m
2 stops
American Airlines Logo
1:48 pm - 9:28 am
STT
-
IND
19h 40m
2 stops
$320American Airlines
Sun, Nov 1 - Wed, Nov 4
American Airlines Logo
6:13 pm - 12:17 pm
IND
-
STT
17h 04m
1 stop
American Airlines Logo
4:33 pm - 11:53 pm
STT
-
IND
8h 20m
1 stop
$320American Airlines
Sun, Aug 30 - Fri, Sep 4
Delta Logo
7:02 am - 1:34 pm
IND
-
STT
6h 32m
1 stop
Delta Logo
2:49 pm - 12:27 am
STT
-
IND
9h 38m
1 stop
$320Delta
Sun, Aug 30 - Fri, Sep 4
Delta Logo
7:02 am - 1:34 pm
IND
-
STT
6h 32m
1 stop
Delta Logo
2:49 pm - 12:27 am
STT
-
IND
9h 38m
1 stop
$365Delta
Thu, Oct 29 - Sun, Nov 1
United Airlines Logo
11:05 am - 9:22 pm
IND
-
SJU
10h 17m
2 stops
United Airlines Logo
8:25 am - 3:00 pm
SJU
-
IND
7h 35m
1 stop
$366United Airlines
Sat, Nov 7 - Sat, Nov 14
United Airlines Logo
10:57 am - 10:22 pm
IND
-
SJU
10h 25m
2 stops
United Airlines Logo
8:25 am - 3:00 pm
SJU
-
IND
7h 35m
1 stop
$366United Airlines
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 $390, 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 $534 (return) on average. On the other hand, the most expensive months are June and December, when the average cost of round-trip tickets is $697 and $683 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

$119
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 4229 reviews
8.0Comfort
7.5Entertainment
7.0Food
8.1Boarding
8.6Crew
Airline reviews

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.

6.0 GoodVera, Jul 2026
MCO - BNA
Read more Southwest reviews

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

Red eye from San Diego. Temperature of the cabin was way too warm and the air duct flowed very little air.

Overall good, just screaming kids in the area the whole flight.

My experience will Southwest was good. I wish there was more entertainment and the boarding process was slow at time but other than that my experience was great definitely will be flying with SouthWest again.

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

Comfortable seats. Nice service online. Short flight, so not a lot of time to enjoy.

Awful. There was an unexpected delay of nearly three hours because there were not enough flight attendants. I understand this is likely due to FAA regulations; but in that case, Delta should coordinate with smaller airports such as RDU to have extra flight attendants on the ground and "on call". In addition, this was the second 2-hour+ delay to Boston on this route in one week.

It was strange that the flight attendant was so adamant about having phones turned to airplane mode that he was calling out names from networks shown and waiting until they were all gone. I've never experienced that before, and after already working through an hour+ delay, it felt tone deaf. I take dozens of flights per year and have never experienced anything similar.

The flight was done by SkyWest only WIFI no entertainment center are available on the CRJ

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 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

Wonderful flight! The crew was good, check-in was good and orderly and the flight was uneventful and good.

Gluten free snack options and meals that offer both gluten free and dairy free.

The pilot was late so we didn’t take off til almost 2 hours late.

The SFO lounge closes at 12 midnight. My flight took off at 2AM

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.

When I booked, I included my checked luggage and when the bill was sent there was no record of this. Its was costly since I am from Trinidad amd Tobago. Exchange rate over seven dollars to one US dollar.

Everything was good except checking bags . I had paid for two bags but it didn’t show so we had to do it again while people waited and we were struggling to get to our flight

Flight delayed 4 times on a non-stop from BOS to SFO. Then when landed in SFO had to wait for 30 mins for a gate AT 3:30AM.

Plane was delayed multiple times. I would like to request a refund. Was due to arrive Thursday evening ended up arriving Friday morning.

The seats were roomier than other airplanes I’ve been on.

The crew and the pilots. The pilots were amazing. The landing in Cancun was excellent.

The security line at JFK was one of the longest I’ve ever experienced - probably 45 minutes. I don’t know if JetBlue has control over it, but it detracted from the overall experience. Entertainment had good options, but the volume control was a bit small to tap on and the screen had a fair amount of interference blips. Clearer picture would have been better.

I liked the entertainment on JetBlue, the service from JFK to JAX was terrible at best

I usually dont fly JeTBlue and I dont think I will ever do it again. The flight was delayed fee time, nobody was giving us any info at at the airport, gate changing, the slowest and poorly organized boarding ever, rude staff.. huh

The flight was delayed. I upgraded to more room. I can't imagine how small the regular seats are I haven't upgraded for my return flight yet.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports