$115 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 8/19. 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 Cana2 stops$432
Santo Domingo
Santo Domingo1 stop$600
Montego Bay
Montego Bay1 stop$410
Oranjestad
Oranjestad1 stop$451
Nassau
Nassau1 stop$342
Kingston
Kingston1 stop$601
Simpson Bay
Simpson Bay1 stop$404
Providenciales
Providenciales2 stops$423
Port of Spain
Port of Spain1 stop$501
Bridgetown
Bridgetown1 stop$439
George Town
George Town1 stop$361
Willemstad
Willemstad2 stops$655
Aguadilla
Aguadilla2 stops$366
St. John's
St. John's1 stop$763
Puerto Plata
Puerto Plata1 stop$700
Punta Cana
Punta Cana2 stops$432
Santo Domingo
Santo Domingo1 stop$600
Montego Bay
Montego Bay1 stop$410
Oranjestad
Oranjestad1 stop$451
Nassau
Nassau1 stop$342
Kingston
Kingston1 stop$601
Simpson Bay
Simpson Bay1 stop$404
Providenciales
Providenciales2 stops$423
Port of Spain
Port of Spain1 stop$501
Bridgetown
Bridgetown1 stop$439
George Town
George Town1 stop$361
Willemstad
Willemstad2 stops$655
Aguadilla
Aguadilla2 stops$366
St. John's
St. John's1 stop$763
Puerto Plata
Puerto Plata1 stop$700

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

Mon, Oct 26 - Wed, Oct 28
Multiple Airlines Logo
2:46 pm - 11:38 pm
IND
-
SJU
8h 52m
1 stop
Multiple Airlines Logo
5:12 pm - 8:39 pm
SJU
-
IND
27h 27m
1 stop
$242Multiple Airlines
Mon, Oct 26 - Wed, Oct 28
Frontier Logo
2:46 pm - 11:38 pm
IND
-
SJU
8h 52m
1 stop
Frontier Logo
4:39 pm - 11:44 am
SJU
-
IND
19h 05m
2 stops
$243Frontier
Mon, Aug 31 - Wed, Sep 9
Multiple Airlines Logo
6:11 pm - 12:56 am
IND
-
SJU
30h 45m
2 stops
Multiple Airlines Logo
5:12 pm - 10:07 am
SJU
-
IND
16h 55m
1 stop
$265Multiple Airlines
Mon, Oct 26 - Fri, Oct 30
Frontier Logo
12:39 pm - 11:57 pm
IND
-
SJU
11h 18m
2 stops
Frontier Logo
5:12 pm - 1:51 pm
SJU
-
IND
20h 39m
1 stop
$266Frontier
Tue, Oct 6 - Wed, Oct 14
American Airlines Logo
6:57 pm - 2:55 pm
IND
-
STT
19h 58m
2 stops
American Airlines Logo
3:46 pm - 9:28 am
STT
-
IND
17h 42m
2 stops
$320American Airlines
Wed, Sep 16 - Wed, Sep 23
American Airlines Logo
6:57 pm - 12:51 pm
IND
-
STT
17h 54m
2 stops
American Airlines Logo
1:41 pm - 9:56 am
STT
-
IND
20h 15m
2 stops
$325American Airlines
Fri, Sep 18 - Thu, Sep 24
Delta Logo
6:00 am - 1:53 pm
IND
-
NAS
7h 53m
1 stop
Delta Logo
1:16 pm - 11:22 pm
NAS
-
IND
10h 06m
1 stop
$342Delta
Fri, Sep 18 - Sat, Sep 26
Delta Logo
6:38 pm - 11:41 am
IND
-
NAS
17h 03m
2 stops
Delta Logo
1:06 pm - 8:48 pm
NAS
-
IND
7h 42m
1 stop
$346Delta
Mon, Aug 3 - Thu, Aug 6
United Airlines Logo
8:00 am - 2:57 pm
IND
-
NAS
6h 57m
1 stop
United Airlines Logo
3:59 pm - 11:44 pm
NAS
-
IND
7h 45m
1 stop
$371United Airlines
Sat, Dec 5 - Sat, Dec 12
United Airlines Logo
9:21 am - 3:03 pm
IND
-
NAS
5h 42m
1 stop
United Airlines Logo
1:05 pm - 11:41 pm
NAS
-
IND
10h 36m
2 stops
$375United 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 $959.

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 $385, 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 $522 (return) on average. On the other hand, the most expensive months are June and December, when the average cost of round-trip tickets is $690 and $676 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

September

Cheapest flight

$115
Best time to beat the crowds with an average 2% drop 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.

  • How many flights are there between Indianapolis and Caribbean Islands per day?

    There is a maximum of 1 nonstop flight a day that takes off from Indianapolis and lands in Caribbean Islands, with an average flight time of 4h 20m. The most common departure time is 10:00 am and most flights take off in the morning. Each week, there are 1 flights.

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 4238 reviews
7.0Food
8.1Boarding
8.6Crew
8.0Comfort
7.5Entertainment
Airline reviews

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

10.0 ExcellentTamara, Jul 2026
MCO - DEN
Read more Southwest reviews

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.

Flight was delayed by 2 hours, meaning that a flight to Dwnver which should have arrived at 11pm came into the airport at 1 am. Made for a very long day.

I think Southwest is the number one airline that anyone can fly I have flown for the first time Frontier and what a joke and their customer service United was a very strange experience I'm only sticking to Southwest from here on out for sure

Great job! My family doesnt fly often but we felt safe 100%

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

This flight was originally delayed by ~45 minutes; which is fine. However, there were additional delays due to late offboarding of the prior flight, unclear issues with the boarding process, delays on the tarmac, and exceptionally long taxiing. None of these issues were communicated proactively. Additionally, the flight had exceptionally rough turbulence, which led to a very uncomfortable flight and no traditional beverage service. Again, this is understandable, but it was not communicated up-front by the flight team.

My flight was canceled, and instead of rebooking me on a non-stop first-class flight for the same day, which I originally had, Delta rebooked me on a one-stop flight for the following day. When I checked the Delta app, I noticed that there were available flights for both the same day and the next day. I believe this indicates poor management on their part.

The Columbus-based WestJet crews that cover Delta commuter flights between LGA and CMH are excellent - this team included. Our flight today landed 40 minutes early, which is unheard of when flying out of LaGuardia. I've flown with the same crew in more challenging conditions, and they always rise to the occasion with helpful communication to the passengers so that we may manage expectations.

Easy on easy off and the staff onboard were wonderful. Left on time, arrived a bit early.

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

I would have preferred a flight voucher and to hop on a different flight. Delayed over 6 hours.

Our flight gor canceled and there was no one to help us but told us to scan the qr code and fill the forms on-line. Very poor service especially we are tourists traveling to Washington DC for the 1st time.

1. Everything was satisfactory concerning the flight. 2. Can't think of what could be better right now.

Onboard staff was courteous, helpful, responsive and friendly. The boarding process was disorganized, poorly communicated, and disheveled. Gate agents were yelling instead of using the PA system, didn’t communicate the timing delay of our flight, and created an atmosphere of chaos rather than order and communication. As far as I know, there was no reason for their. I would hate to see how it operated under extreme conditions. I’ve never seen United Airlines operations in such a state.

Baggage claim signs were not updated with my flight information, so I had to guess. The app wasn't updated either.

I almost missed my connection in Chicago due to having to wait on a gate to be open I am assuming. Having to run from E terminal to C terminal and I barely made it there before they closed the door. This may not be the actual airline's fault it's crazy how there is so little time between flight especially when they are placed so far apart in the airport.

Unbelievably smooth boarding at IAH and the flight attendants were top notch.

We flew business fares. Was amazing. However, the check in didn't offer business fares preboarding which is less hectic. 8/10 due to this. Staff compared to Canadian carriers go above and beyond. Would gladly fly United again.

It was extremely hot in the cabin the entire flight, vent air was worn

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.

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.

Entertainment was okay not because anything was wrong but it is a short flight so having no wifi is annoying but understandable. Crew was outstanding as usual

I am tired of being nickel and dimed for seat location, checked luggage and carry on bags. That is why i rarely fly anymore.

Did not get to Ontario yet. Sitting on tarmac for 2 plus hours.

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.

see my previous response about being kicked off the flight and having to fly the next day, ruining a planned vacation tour.

Horrible - for the first time in my life i was denied boarding an international flight because the name used on my ticket - Josh - was not exactly the same as my passport - Joshua. At no time during ticketing, online check-in, or at the airport flying from Boston to NY was i notified of a problem. It was only at boarding from NY to Costa Rica I was informed of the problem and by then it was too late. After missing the flight I was told by airport Jet Blue staff, including a supervisor, that it was my problem and they could not assist because i bought "the cheapest fare". i was hung up on twice by JetBlue customer service, including once by a supervisor. I blame Kayak and your awful partner ChatDeal for even allowing me to purchase an international ticket without verifying this - you effectively sold me a ticket i could not use. Shame on you and shame on ChatDeal for doing nothing to help me resolve the situation. What a scam.

Like the variety of entertainment options. One crew member was a little on the rough/rude side. Boarding was a mess, attendants didn't do a great job of helping with the luggage storage and it delayed us a couple of minutes.

It was a smooth flight and the pilot was very pleasant

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports