$68 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 1/4. 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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Search 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
In the last 7 days travelers have searched 41,299,237 times on KAYAK, and here is why:

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Best Caribbean Islands Flight Deals from Indianapolis

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

Punta Cana
Punta Cana1 stop$299
Santo Domingo
Santo Domingo1 stop$343
Montego Bay
Montego Bay1 stop$277
Oranjestad
Oranjestad1 stop$337
Nassau
Nassau2 stops$363
Simpson Bay
Simpson Bay1 stop$408
Kingston
Kingston1 stop$320
Providenciales
Providenciales1 stop$527
Bridgetown
Bridgetown2 stops$624
Port of Spain
Port of Spain1 stop$587
George Town
George Town1 stop$526
Willemstad
Willemstad1 stop$538
Puerto Plata
Puerto Plata1 stop$567
St. John's
St. John's1 stop$650
Aguadilla
Aguadilla2 stops$334

Good to know

Low season

August

High season

March

Cheapest flight

$68
Best time to beat the crowds with an average 7% drop 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.

See more FAQs

Top tips for finding cheap flights to Caribbean Islands

  • Book at least 1 week before departure in order to get a below-average price.
  • High season is considered to be January, November and December. The cheapest month to fly from Indianapolis is January.

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.
8.1
SouthwestOverall score based on 4821 reviews
8.1Comfort
8.7Crew
7.2Food
8.2Boarding
7.7Entertainment
Airline reviews

I recently flew Southwest from San Jose to Honolulu. I was very impressed with the flight crew, especially the flight attendant in charge of the front of the plane. She came through the aisle at least five times for drinks and water, and two times for snacks. I have not seen such service since I flew first class. Also, for the first time, they gave us the correct baggage claim number, and the luggage came out quickly. I can't wait for Southwest to have assigned seating! I absolutely hate the Cattle Call boarding procedure and the mad dash to get seats and overhead bins. However, the boarding was efficient.

10.0 ExcellentWilliam Drew, Dec 2024SJC - HNL
Read more Southwest reviews

I recently flew Southwest from San Jose to Honolulu. I was very impressed with the flight crew, especially the flight attendant in charge of the front of the plane. She came through the aisle at least five times for drinks and water, and two times for snacks. I have not seen such service since I flew first class. Also, for the first time, they gave us the correct baggage claim number, and the luggage came out quickly. I can't wait for Southwest to have assigned seating! I absolutely hate the Cattle Call boarding procedure and the mad dash to get seats and overhead bins. However, the boarding was efficient.

Crew was great flight was great baggage claim was a failure. It took over 1 hour for bags to arrive. Poor communication poor effort when I spoke to the supervisor about the delay

Much better than the.last. flight on SW on Thanksgiving day

Fine, but how to board on SW versus othrr airlines, is just lame. Goood staff though and all was solid otherwise.

The movies using Southwest WiFi kept pausing and I had to restart multiple times.

It went well. Plane wasn't full. Will be great when assigned seating is in place

Everything was great except the food. The pretzels are really crappy.

For the first time in a long time we had a flawless experience with Southwest. Both flights were early and no mechanical errors at all. We were shocked and pleasantly surprised 😮.

It was fine. For some reason the flight was much longer than usual. It may have been explained, but I had noise cancelling earbuds on and missed a couple of announcements. The crew was fine, but there was a flight attendant who kept telling dumb jokes, occasionally one I found distasteful. This was my second time with him, but luckily it was a late flight so he didn't do as many. But I heard all of today's jokes twice, which was two times too many. Good takeout and landing.

One of the crew performed a hilarious skit to accompany the standard instructions. Passengers enjoyed it so much they applauded at the end!

I was with one of the last zones to board. It was kind of annoying to finally get called to board and my whole section was already on the plane. Clearly they boarded with previous zones. So by the time I got on board, there were no spaces for my luggage above my head. I had to put my luggage 4+ rows behind me, which meant that I had to wait even longer to get off the plane, since I had to wait for those rows to clear the aisle before I could retrieve my luggage and exit the plane. This also held up the plane cleaners, as they couldn't service my row until I cleared it, so they were all standing there waiting for me, while I'm standing there waiting for the other passengers to clear the aisle. Anyways, I wasn't in a rush this time, so I just waited, but I could see that being a problem in the future. Now, I could have checked my luggage, of course, but coincidentally, a friend of mine on the same flight got their luggage damaged (wheel completely knocked off) and was told by the Baggage Attendant in the airport that Delta doesn't "cover wheel damage" on luggage. This was disappointing to hear. I'm glad I didn't check mine through. If it were my luggage, I'd be highly frustrated to hear that. It makes me not want to check my luggage in the future.

The dear was very limited in space. I could put my water bottle in seat basket. Also, there was no inflight entertainment in the delta app?

Typically I give delta excellent reviews. Our flight was delayed 2hrs, I was one of the fortunate ones who were able to get to my connecting flight. Also, annoying that on the connecting flight boarding personnel make me put away a small bag into my carryon. It small enough to put in back pocket seat, why hold me and the line up to just push it into my carryon.

Logan airport construction meant that boarding was chaotic crowded and delayed

Everything was great. Great service, excellent communication, and early arrival

We were forced to wait nearly 50 additional minutes before leaving the terminal.

Free Wi-Fi is good. That’s all - food mediocre, unfriendly crew, poor communication after trying to file a claim for my lost bag, which Delta didn’t even know was lost until I told them.

Delta flight attendants poorly managed the boarding process and overhead storage. My bag was checked last minute and no claim ticket was provided. My bag is now lost. Complete incompetence by all flight crew involved.

Inexpensive, got an exit row aisle aeat with no middle passenger, bought a great breakfast sandwich, flight comfortable & arrived ahead of schedule.

Customer service at the gate in the flight was exceptional. On time. Aircraft and seat was decent. Thanks Delta. 💗

We arrived early and finally made it to our gate almost an hour after.

The reason I don’t fly United. No in seat entertainment for a long flight and inconsistent WiFi and entertainment available from my device.

We were delayed 3x and because I didn’t purchase my tickets directly from United Airlines I was told I Have to take care of it myself so I called Underpricer and they helped me but before I changed my flights I took the risk of sticking by what my tickets were and was lucky to have gotten on the original all flight with only 15 mins before take off. not sure if I will do this again

horrible website for checking in- no option just to write the passport number; ludicrous

The planes are so dirty! Food crumbs and finger print smudges, Dust over the vents and carpet stains. It’s disgusting.

Everything good until we waited for jet bridge at SFO. Then pilot gets on speaker & said it won’t reach plane- too short, need to go to different gate. Then 5 min later, adjusted plane/jetbridge & all ok?!?

Nothing, whole flight was a nightmare, was forced to check my carryon bag at the gate, staff was rude and unprofessional

David went above and beyond to make our flight the best that it could be

Was a pain having to leave the plane and reboard but glad the plane was fixed

How badly can you screw up baggage claim? We were told to go to baggage claim too for our bags from this flight. Another flights bags were there. They finished up. More bags from a different flight arrived. Our bags did not Finally the baggage claim belt stopped working and and are flight was still listed on the arrivals for that baggage claim 2. And then nothing It turns out that they had been delivered not only the United baggage claim but far away on a Delta baggage claim No I never told us. It was only the people looking around who had been on the flight But I’m sure there was plenty of time for the employees to raffle through the bags and steal whatever they wanted

Other than being delayed 5.5 hours and having to get a hotel because I missed my connecting flight, it was an okay flight. No in-flight Wi-Fi or entertainment.

Flight areas delayed 3 hours , train in the airport didn’t work

Flight attendant walked away once they landed and we were forced to wait another hour after an already 3hr delay.

No overhead space so all carryons were checked. No internet.

The flight was on time and everything went very smoothly.

A thousand choices for movies and nothing to watch. I avoid 'R' rated shows and others with violence and sexual content, which results in a handful of flicks to view and I have them already.

I think I paid for an extra legroom seat and to be honest, there was not a lot of space available for my not very long legs. The flight was totally full and the staff did everything possible to meet the needs of all passengers. My only concern was for the size and spacing of my seat.

Typically, I am always impressed with American personnel. These you run into the rude old hags that are still around. I can tell over my 40 years of flying with them, they have made strides in improving their attitudes.

Two issues. The plane was old and dirty. The armrest looked like an old car that had the vinyl rubbed off. The Seats in these aircraft are about as hard and uncomfortable. I want to tour Italy for a month and I want to buy a one-way ticket to Thailand but I will not sit in the seats these planes have. It is seriously stupid how hard they are.

The seat could not recline. This was not indicated as such when I paid for the seat. So itvwad not the most comfortable ride. At boarding, the staff could have more pleasant even though it may be an intense time.

I was comfortable because I upgraded. I would not have been comfortable in economy. It was a short flight so there was limited food service and no inflight entertainment.

I thought since I upgraded my seat I would get some perks. Free water, free snacks. Free carry on luggage.

Seats were surprisingly comfortable, and crew was polite. I did not like the baggage fee prices, the minimal amount of flight choices for my area and the difficulty of the self service bag drop.

Lost MacBook, had time to retrieve, but was told I had no time. Need Silver MacBook back

It’s ridiculous to pay for carry-on luggage. I also wasn’t given an option to specify I have carry on bag at time of ticket purchase. I also could not specify I have carry on luggage at time of online check-in.

I’ve now flown Spirit a few times and while the general perception of Spirit I feel is poor, I’ve had a great experience each time. They do charge extra for everything but you should know that going in

The people were wonderful, but I hated the way they over charged for luggage, especially for stops which were charged the same as starting point to final destination.

Horrible I paid for extra for better seats. At time of checking my seats were sold to someone else. I need a refund and more for my bad experience

First time flying Spirit and I was pleasantly surprised. Service was as advertised. Crew were very professional and friendly and excellent in dealing with a customer who felt ill on the flight.

Delayed fight LAS to LAX. OK, fog in LA, not your fault. But all your staff, onboard in in lounge, speak so fast, enunciate so poorly and often have a accent that it is impossible to understanding anything they are saying.

Book cheap flights from Indianapolis to Caribbean Islands

Recent round-trip flight deals

 
These are the cheapest round-trip flights from Indianapolis to Caribbean Islands found on KAYAK in the last 72 hours.
1/18Sat
1 stop
21h 55mIND-SJU
1/25Sat
1 stop
13h 20mSJU-IND
$174
2/12Wed
1 stopSpirit Airlines
15h 37mIND-SJU
2/19Wed
2 stopsSpirit Airlines
15h 26mSJU-IND
$209
1/13Mon
1 stopDelta
10h 14mIND-SJU
1/16Thu
1 stopDelta
7h 39mSJU-IND
$264
2/5Wed
2 stopsAmerican Airlines
9h 30mIND-SJU
2/8Sat
2 stopsAmerican Airlines
9h 46mSJU-IND
$284
2/19Wed
1 stopDelta
6h 51mIND-SJU
2/20Thu
1 stopDelta
8h 44mSJU-IND
$294
2/22Sat
2 stopsAmerican Airlines
8h 45mIND-SJU
2/28Fri
2 stopsAmerican Airlines
8h 22mSJU-IND
$304
2/4Tue
2 stopsUnited Airlines
10h 56mIND-SJU
2/6Thu
2 stopsUnited Airlines
11h 46mSJU-IND
$314
1/14Tue
1 stopUnited Airlines
7h 35mIND-SJU
1/14Tue
2 stopsUnited Airlines
11h 46mSJU-IND
$348
1/12Sun
2 stopsSouthwest
12h 15mIND-SJU
1/18Sat
2 stopsSouthwest
10h 45mSJU-IND
$449
2/3Mon
2 stopsSouthwest
11h 25mIND-SJU
2/9Sun
2 stopsSouthwest
11h 20mSJU-IND
$523

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Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Indianapolis to Caribbean Islands found on KAYAK in the last 72 hours.
1/4Sat
1 stopFrontier
14h 13mIND-SJU
$68
1/1Wed
1 stopFrontier
16h 21mIND-SJU
$87
1/14Tue
3 stopsSpirit Airlines
28h 16mIND-STT
$120
1/14Tue
2 stopsSpirit Airlines
16h 14mIND-STT
$127
1/15Wed
1 stopUnited Airlines
8h 55mIND-NAS
$128
1/23Thu
2 stopsUnited Airlines
10h 02mIND-SJU
$132
1/10Fri
2 stopsAmerican Airlines
9h 09mIND-PUJ
$185
1/30Thu
2 stopsAmerican Airlines
9h 01mIND-SJU
$192
3/20Thu
1 stopDelta
9h 00mIND-SJU
$212
1/14Tue
1 stopDelta
7h 14mIND-STT
$226

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Last minute flights from Indianapolis to Caribbean Islands

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from Indianapolis to Caribbean Islands that are departing in the next 10 days.
12/23Mon
multi-stopDelta
8h 59mIND-SJU
12/26Thu
multi-stopDelta
10h 46mSJU-IND
$324
12/21Sat
multi-stopAmerican Airlines
17h 15mIND-SJU
12/28Sat
multi-stopAmerican Airlines
12h 21mSJU-IND
$434
12/22Sun
multi-stopAmerican Airlines
16h 06mIND-SJU
12/26Thu
multi-stopAmerican Airlines
13h 55mSJU-IND
$458
12/21Sat
multi-stopUnited Airlines
8h 55mIND-NAS
12/24Tue
multi-stopUnited Airlines
6h 50mNAS-IND
$587
12/25Wed
multi-stopDelta
8h 12mIND-STT
12/29Sun
multi-stopDelta
9h 55mSTT-IND
$603
12/25Wed
multi-stopSouthwest
7h 05mIND-GCM
12/30Mon
multi-stopSouthwest
7h 15mGCM-IND
$616
12/25Wed
multi-stopSpirit Airlines
18h 17mIND-STT
12/29Sun
multi-stopSpirit Airlines
26h 42mSTT-IND
$621
12/25Wed
multi-stopSpirit Airlines
12h 31mIND-SJU
12/29Sun
multi-stopSpirit Airlines
10h 16mSJU-IND
$637
12/21Sat
multi-stopUnited Airlines
5h 50mIND-NAS
12/24Tue
multi-stopUnited Airlines
22h 13mNAS-IND
$682
12/23Mon
multi-stopSouthwest
9h 50mIND-SJU
12/26Thu
multi-stopSouthwest
9h 35mSJU-IND
$729

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Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports

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