$104 Find Cheap Flights from Indianapolis to Caribbean Islands

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 9/20. 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.
1 adult
1 adult, Economy

KAYAK searches hundreds of travel sites at once for deals on flights to Caribbean Islands

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Indianapolis to Caribbean Islands, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Indianapolis to Caribbean Islands, as well as popular online travel agencies
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Flight Deals

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$319
Santo Domingo
Santo Domingo1 stop$338
Montego Bay
Montego Bay1 stop$304
Oranjestad
Oranjestad1 stop$444
Nassau
Nassau1 stop$413
Simpson Bay
Simpson Bay1 stop$342
Kingston
Kingston1 stop$389
Providenciales
Providenciales1 stop$356
Port of Spain
Port of Spain2 stops$554
Bridgetown
Bridgetown1 stop$586
George Town
George Town1 stop$496
Willemstad
Willemstad2 stops$545
St. John's
St. John's2 stops$565
Puerto Plata
Puerto Plata1 stop$525
Aguadilla
Aguadilla2 stops$550
Punta Cana
Punta Cana1 stop$319
Santo Domingo
Santo Domingo1 stop$338
Montego Bay
Montego Bay1 stop$304
Oranjestad
Oranjestad1 stop$444
Nassau
Nassau1 stop$413
Simpson Bay
Simpson Bay1 stop$342
Kingston
Kingston1 stop$389
Providenciales
Providenciales1 stop$356
Port of Spain
Port of Spain2 stops$554
Bridgetown
Bridgetown1 stop$586
George Town
George Town1 stop$496
Willemstad
Willemstad2 stops$545
St. John's
St. John's2 stops$565
Puerto Plata
Puerto Plata1 stop$525
Aguadilla
Aguadilla2 stops$550

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

Wed, Oct 8 - Wed, Oct 15
 Logo
5:15 am - 3:24 pmIND-SJU
10h 09m1 stop
 Logo
6:22 am - 5:07 pmSJU-IND
10h 45m1 stop
Tue, Oct 7 - Wed, Oct 15
 Logo
5:15 am - 3:24 pmIND-SJU
10h 09m1 stop
 Logo
6:22 am - 5:07 pmSJU-IND
10h 45m1 stop
Tue, Oct 28 - Tue, Oct 28
United Airlines Logo
5:45 am - 12:17 pmIND-SJU
6h 32m1 stop
United Airlines Logo
4:50 pm - 11:59 pmSJU-IND
7h 09m1 stop
$230United Airlines
Find Deal
Wed, Oct 22 - Tue, Oct 28
Delta Logo
7:29 am - 4:25 pmIND-SJU
8h 56m1 stop
Delta Logo
7:00 am - 4:19 pmSJU-IND
9h 19m1 stop
$235Delta
Find Deal
Fri, Oct 24 - Tue, Oct 28
American Airlines Logo
11:05 am - 11:59 pmIND-SJU
12h 54m1 stop
American Airlines Logo
11:56 am - 11:44 pmSJU-IND
11h 48m2 stops
$236American Airlines
Find Deal
Tue, Oct 7 - Sat, Oct 11
American Airlines Logo
6:00 am - 2:08 pmIND-SJU
8h 08m1 stop
American Airlines Logo
5:30 am - 5:45 pmSJU-IND
12h 15m1 stop
$240American Airlines
Find Deal
Sun, Sep 28 - Sat, Oct 4
Spirit Airlines Logo
6:25 pm - 11:04 amIND-SJU
16h 39m1 stop
Spirit Airlines Logo
3:19 pm - 11:11 pmSJU-IND
7h 52m1 stop
$243Spirit Airlines
Find Deal
Tue, Sep 30 - Tue, Oct 21
Spirit Airlines Logo
5:45 am - 2:11 pmIND-SJU
8h 26m1 stop
Spirit Airlines Logo
2:49 am - 9:20 amSJU-IND
6h 31m1 stop
$269Spirit Airlines
Find Deal
Sat, Oct 25 - Wed, Oct 29
Delta Logo
6:30 am - 1:12 pmIND-SJU
6h 42m1 stop
Delta Logo
7:00 am - 4:19 pmSJU-IND
9h 19m1 stop
$270Delta
Find Deal
Tue, Sep 30 - Tue, Oct 21
United Airlines Logo
11:27 am - 11:57 pmIND-SJU
12h 30m2 stops
United Airlines Logo
1:05 am - 9:12 amSJU-IND
8h 07m1 stop
$297United Airlines
Find Deal
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 72 hours was to Punta Cana, at $613 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 72 hours was $613.

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 $307, 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 September, when tickets cost $265 (return) on average. On the other hand, the most expensive months are December and August, when the average cost of round-trip tickets is $517 and $433 respectively.

What’s the cheapest day of the week to fly from Indianapolis to Caribbean Islands?

The average price of all round-trip flights from Indianapolis to Caribbean Islands clicked on KAYAK for each day over the last 12 months.

Your flight ticket price will generally be cheaper if you fly to Caribbean Islands on a Tuesday and more expensive on a Sunday. On your return trip to Indianapolis, you should consider flying back on a Thursday, and avoid Mondays for better deals.

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 1 week before departure. For the absolute cheapest price, our data suggests you should book 3 weeks before departure.

Good to know

Low seasonJuly
Cheapest flight$104
Best time to beat the crowds but there is an average 8% increase in price.
Most popular time to fly with an average 8% 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.

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

    The cheapest time of day to fly to Caribbean Islands is generally at night, when round-trip flights cost $304 on average. Morning departures are around 7% more expensive than evening flights, 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 $422.

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 4248 reviews
8.0Comfort
7.5Entertainment
7.0Food
8.6Crew
8.1Boarding
Airline reviews

I wish they had movie screens in the headrests. The seats are much improved, more legroom and recently renovated. Bathroom was clean. Staff was outstanding!!

10.0 ExcellentG, Sep 2025LAS - ATL
Read more Southwest reviews

I wish they had movie screens in the headrests. The seats are much improved, more legroom and recently renovated. Bathroom was clean. Staff was outstanding!!

As always, the entire Southwest experience was wonderful, from online booking to flight to baggage retrieval. Very grateful.

The weather could have been better. There was a 40 minute ATC delay in SFO because of marine fog and a micro cell storm delayed landing and take-off at Nashville. The gate was changed 5 minutes from boarding from gate B3 to gate C23 at Nashville airport.

After being assaulted by a flight attendant I was then brushed off as oh well because he long braids didn’t mean to whip me in the eye. I have filed complaints and will see. But like any other issue I’ve had with kayak involved it’s been trash. Last time I’ll be using your app

AC sub par. WiFi not working correctly. Ac sucked. Seats very narrow.

Near 4 hour flight with only 1 service. Had to use call button to request water. Internet and power not working until into flight. Internet would stop working during flight.

Southwest's seats are the least comfortable I have ever sat in.

The cabin was quiet for the redeye flight. The area was clean. The staff was great. The 787 Max was in good condition. Drawbacks were that the seat widths were tight for some passengers. The seat padding was at best average and for a long flight uncomfortable.

Southwest like most American domestic airlines, is a mediocre airline. But it is among the cheapest. Oh well.

My flight was delayed 50 minutes and we were rushed to board to then sit for 15 minutes until the pilot arrived. Unacceptable since we could have waited to board. Also the delayed flight was updated AFTER we boarded to more than the 10 minutes as originally stated.

Perfect flight both ways. On time, courteous staff, plane comfortable and cool. Best domestic flights I’ve had in awhile.

The food was terrible especially for a 15 hour international flight. The crew was unpleasant as well.

Really low quality food especially for an international flight. The crew also was surprisingly unpleasant except couple of ladies. I know we were not in first class but that’s no reason to treat customers as less.

Flight delayed for two and half hours and then canceled altogether due to mechanical issues. No mechanic onsite to fix so had to send one from LAX.

Quick check in. Everything went smooth. I don't know what can be done about airline food.

Crew was good. The reservation got mixed up and they didn't have my TSA number. I am also a Silver Medallion and wasn't able to use Sky Priority.

Delta made it easy, comfortable and timely. The crew was fantastic.

This route with Delta always has delays or is cancelled. Aircrafts seem smaller and older. I fly Delta quite a bit - haven’t had issues with the international flights. But this route has always been the troublesome one

Nothing special. The crew never went out of their way for anything.

Three seats in first class were broken and while they were able to still acommodate us it was looking very touch and go and they had others they could not acommodate

We had to deboard 2 times due to maintenance issues. They changed the plane, and then we got deviated to LAX due to maibtenance issues on the other plane, had to sleep at LAX and los a full day.

Everything was good, except the seats in economy were so close together, you could barely get out when the seat in front of your was reclined. If the airlines keep jamming in more and more seats, it will become intolerable. I will look for another airline that considers customer comfort and does not keep adding more rows of seats for more profit.

The newer screen was super cool and had the option to watch many different shows or movies. Crew was polite and helpful. However again, many children screaming bloody murder and kicking my seat, and parents doing nothing about it as usual.

Flight was good and crew was super polite. However, there were around 5 kids screaming the WHOLE 2 hours. I understand kids have to come but parents need to do something to control their children. They make the experience terrible, especially after finishing 16 hour shifts at the hospital I needed some sleep, which I did not get.

IAD with the archaic people movers is just a place to be avoided.

Great service on board. Boarding a bit slow due to process. Food was pretty average.

Tastless food and too obvious lack of enthusiasm for service in the economy vesus business class

All of the United employees I interacted with were professional and courteous. The aircraft was clean, the food on the flight was good. No complaints here.

I had no checked baggage but was required to hand over carry on baggage at the door of the plane. There was a lot of overboard space in the plane and I was one of the last ones. I ran to get my carry on but it was gone. I was given back at the plane door in Toronto, so the wait was not as long as it would have been at the carousel.

Armrest controller on my seat 35D and nextbooennseat 35E did not work right. Hard to press buttons to recognize and 35D had constantnpressure either upmost down somit was nearly impossible to make selections. .

Given it’s a red-eye into Charolotte, we didn’t get any food. The survey does not include “N/A” so the rating will be skewed.

Great. Quick and quiet and east. The breakfast choices were a welcome surprise!

American airlines suck they delay the flights all the time made me sleep in an airport because my flight was delayed and I miss my connecting flight

There's nothing I liked about it. For first off I scheduled this trip two weeks in advance then they delayed my flight which messed up my whole trip. So I scheduled it for the following weekend thinking there won't be a delay and guess what as soon as I got to the airport we said in the airplane on the tarmac for an hour and a half. Not only was it delayed I missed my connecting flight meaning I had to stay the night at Dallas-Fort Worth airport sleeping on the floor. I will tell you this I will never fly American airlines ever again I have had nothing but horrible experience with them and I just throw money at them

The stewardess hit me with the food kart twice on the head and didn't say I'm sorry once. The same stewardess gave me a warm Apple Juice with No ice. The Flight was delayed for Departure 6 times, starting from 2:36pm, finally taking off 7:50pm. I was late picking up my child from the sitter by 3 hours.

Don’t know they cancelled the flight day before I was to leave. They sent a email at 9:00 pm at night saying they cancelled. That is the smooth way to say we don’t want your business! I think they didn’t have enough people booking so they cancelled the flight! It’s all about the money anymore there is no honesty in business.

Having to reschedule flights a day later, they loaded by luggage on the wrong plane from Little rock now I have to HOPE they deliver it to where im staying like they said would. International flight crew was very disgruntled and not very friendly.

We will be writing a long, detailed letter to corporate about our awful experience with American airlines.

It took way too long to diagnose and solve the problem of a broken crew member cabin seat. Though compensation for the volunteer who left the flight was very kind.

The entertainment package was vast and the selections were very current. Keep updating it was great.

Everything was fine. I'm average height and I pack light. I'm ready for my Spirit flight.

Changing the flight time to 6:15 am on the return flight is extremely inconvenient. The flight was okay. It was on time. The crew was friendly. The seats were uncomfortable. All the upsells are annoying, and I would prefer paying a single higher fee and not have to purchase so much extra.

Spirit Airlines was ok but TRAVELHELPDESK, the 3rd party travel agent IS A JOKE! VERY RUDE CUSTOMER AGENTS ont he phone. NO HELP AT ALL. But the airlines was ok.

No Tumberlence smooth flight. Try to change the menu on Snacks.

Cancelled my flight last minute and did not help me rebook. It was a horrible experience.

No frills - because you get what you pay for. The crew was amazing!! I had plenty of room to spread out because the flight was half full. Which made it easy to sleep.

The terminal crew is so rude cabin crew is extremely rude flight is very good

Spirit is low fare air line. Food also cost you. No free food.

The flight was delayed twice with minimal explanation. The terminal and airplane were filthy. The food voucher didn’t even cover a tiny pizza from a kiosk in the terminal. All in all, a pretty miserable experience for a flight to attend a funeral

I will use spirit more New clean aircraft Excellent crew ! Quick boarding process !

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports

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