$65 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 3/11. 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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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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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$297
Santo Domingo
Santo Domingo2 stops$358
Montego Bay
Montego Bay1 stop$333
Oranjestad
Oranjestad2 stops$328
Nassau
Nassau1 stop$345
Kingston
Kingston1 stop$341
Simpson Bay
Simpson Bay1 stop$343
Providenciales
Providenciales1 stop$526
Bridgetown
Bridgetown1 stop$603
Port of Spain
Port of Spain1 stop$410
George Town
George Town1 stop$484
Willemstad
Willemstad1 stop$592
St. John's
St. John's2 stops$692
Puerto Plata
Puerto Plata2 stops$604
Aguadilla
Aguadilla1 stop$287

Good to know

Low season

August

High season

March

Cheapest flight

$65
Best time to beat the crowds with an average 8% drop in price.
Most popular time to fly with an average 3% 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 November and December. The cheapest month to fly from Indianapolis is September.

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 4411 reviews
8.7Crew
7.1Food
8.1Comfort
8.2Boarding
7.6Entertainment
Airline reviews

Gate agents were informative and friendly… flight attendants were as well. Had a fun time chatting about their legacy AirTran experiences as a former fan of the airline that Southwest acquired.

10.0 ExcellentAnonymous, Jan 2025ATL - LGA
Read more Southwest reviews

Gate agents were informative and friendly… flight attendants were as well. Had a fun time chatting about their legacy AirTran experiences as a former fan of the airline that Southwest acquired.

Flight was awfully bumpy and landing was a bit jolting. I was in the restroom when snacks and drinks were served and was not asked if i wanted any. I had to ask for water finally.

Wi Fi was horrible kept cutting out the whole time and too expensive

I really like open seating. I hate that I've heard this is going away. This is one of the unique things that makes Southwest my goto choice.

Boarding was a little late, but made up for it. It was quick to taxi to the runway, since it's a smallish airport.

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

Multiple delays and gate changes. Arrived at final destination 6 hours late. All rental cars had been taken.

Employees were kind and funny, as always! Flight was late but no announcements were made for people with tight connections to help them transition quickly. No service due to turbulence.

It was 2 hours 45 minutes late, for no apparently clear reason.

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.

Boarding is, as it always is… horrible. Gate lice. Slow moving zones. Too many people with carry ons

I loved having a most black flight crew during Black History Month; rather by design or accident I appreciated the representation. ❤️

This was the second flight this week with flight attendant Marcus I’m not sure if his last name is Lane or Lang but this guy is awesome. He funny, attentive and his service is 5 stars. Marcus makes business travel more enjoyable !

Although the flight left late, we arrived early. It was one of the quickest boarding and off boarding experiences I’ve had. It was kind of annoying the only drinks they had were water, coffee, and tea. The flight was very smooth, temperature was just right, and flight attendants were friendly.

Rode in a smaller plane and short trip meant no snacks, no free wifi or tv. It was only 30min flight so honestly wasn’t a big deal to lack these items.

Lower number on this flight so spaced out passengers. Able to enjoy more room to relax during flight. It was lovely.

Kind staff. Snacks are small but that’s the new normal.

Overall, terrible. Flight from SFO was delayed due to “air traffic control issues”, and we were all mislead about connecting flights. Told “you have 20 minutes to catch your connection”. Reality was 5. We got to watch the plane sit at the bridge. Won’t fly Delta with a connection again.

The young man who was our flight attendant in first class was lazy and did not do his job well at all. Never offered drinks upon boarding - actually I take that back... said "are you okay with water" as if I do not want to get you anything else, only passed the snacks around once, got my drink order wrong and then never offered a second round of drinks. He was the worst I have ever seen on Delta and we fly a lot.

Great service. Great staff. Boarding was a little slow, but I think there was a service dog slowing things down.

I don’t understand the purpose of the orange “priority” tag on my bag. This tagged, my bag is last or near to the last bag to come down the carousel at IAH.

The tv monitor in front of my seat was not responding. The flight crew reset it and it still didn’t work.

The agents was very rude and they charged me $50 for a carry-on bag saying that it was too big and then I saw someone going on a plane with the same size bag as me

Liked nothing. As per previous segment it was delay delay delay.

Terrible. First of all we were delayed 4 3/4 hours departing Honolulu. As we had to leave our condo and the rental car had to be returned we had to go to the airport. Even though we had a business class boarding pass to Washington, since we did not have business class to Montreal we could not access the lounge without paying a $59 fee each. This does not make sense to us. Since we could not meet our original connection United booked us to Montreal via New York LaGuardia on Air Canada. In Washington a further delay got us into LaGuardia too late to make our connection to Montreal so we were booked on another Air Canada flight 3 hours later. We were originally scheduled to arrive in Montreal at 10:40 and arrived at 19:55. A totally exhausting day, United did not offer a meal voucher or any type of compensation. Air Canada did give us a digital meal voucher. The food in United business class is poor among all meals offered. The pods look nice but are not that confortable. Overall would not fly on United again.

Plenty of room for me and the cat in Premium Economy. Seat was comfortable. Boarding was a breeze. The lady at the special check-in desk was great, super helpful and professional.

For the most part united was a good experience, how ever when they came by with the snacks and water, they completely passed by my wife and I. As we were in separate rows. On a 5 hr flight we were not offered water

Fantastic crew. Flight was delayed at last minute but we were given updates every 20 minutes and the crew was so friendly and considerate. I miss the touch screens on the back of the seats, wish they would bring that back though.

Our seats were all the way in back of the plane,

Food choices were very limited. Taste of the dishes was average.

The boarding experience was good; $20 for wifi per flight is uncompetitive compared to Delta, Southwest, and others, and puts American lower on my list given similar pricing.

Great experience. Flight boarded easily. Departed early. Smooth flight. Great arrival in DC--almost no taxing! Almost direct to gate from runway. Crew was terrific. Same cookies and beverages in main cabin. I did not use the entertainment system on this flight.

Delays on all NY flights. There was no communication on why but they didn’t say it was weather. Other carriers were not delayed.

The flights were terribly delayed and then cancelled which forced us booking another night at the hotel. Very poor management from American Airlines

Extraordinary service in business class, and very good breakfast and snacks. A really lovely flight.

Same as before being upgraded to business class made it perfect

I flew out of Reagan National. My flight was delayed, delayed, delayed, and then canceled ...THREE TIMES over TWO DAYS. Staff were seemingly not empowered to provide information on why the flights were screwed up. A real nightmare.

They cancelled our flight without warning OR a refund. Never doing business with American Airlines again! This is the second AA booked trip in a row that we've had challenges with.

Crew was late. Baggage was late. 2hs inside the plane waiting fro de-icing and traffic. A 3:30hs flight ended up being almost 6hs inside the airplane.

Flight delayed on both ends - have a gate ready at DCA, don't make us sit for 30min after being late to take off as well.

Flight was on time It was a good flight overall

Check in at dtw was understaffed and chaotic. Flight itself was smooth. Airplane seats seemed newly upholstered and comfortable, flight attendants attentive.

Amazing flying experience, even in not the best of weather. The staff made us comfortable and the flight was actually pretty smooth.

The plane flew smoothly and the crew was polite and kind. We loved our flight!

Your crew is a representation of your Standards and Values. The crew from Seattle to LAX, was very disappointing. The crew was more interested in hanging out at the lobby area. Talking, laughing loudly and eating all the snacks. They did not do regular rounds to see if customers needed anything. This was a huge disappointment. I will no longer be flying with your airlines moving forward.

The senior flight attendant was engaging, funny and made everyone feel at ease. She is an asset to your team.

Terrible-extreme delay with very little communication, plane was overfull, luggage was returned on baggage claim in filthy condition.

Needs legroom for tall people. Needs to offer a glass of water.

Seats are very uncomfortable pls make your seats comfortable pls pls pls

They changed our departure time 6 times before I even reached the airport. Delayed, Ontime, Delayed Back on time, Then Delayed. We finally boarded the plane and then we had to sit on the runway for over an hour only to be told they were taking us back to the gate for an additional 2 hour delay. Lack of communication and a complete waste of time! Never again!

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.
3/6Thu
1 stopFrontier
7h 28mIND-SJU
3/10Mon
1 stopFrontier
12h 08mSJU-IND
$151
5/8Thu
1 stop
9h 19mIND-SJU
5/12Mon
1 stop
17h 02mSJU-IND
$164
3/4Tue
2 stopsSpirit Airlines
22h 20mIND-SJU
3/11Tue
2 stopsSpirit Airlines
29h 14mSJU-IND
$189
4/1Tue
2 stopsSpirit Airlines
15h 07mIND-STT
4/3Thu
1 stopSpirit Airlines
9h 43mSTT-IND
$190
4/18Fri
2 stopsAmerican Airlines
18h 17mIND-STX
4/23Wed
2 stopsAmerican Airlines
18h 57mSTX-IND
$305
3/12Wed
2 stopsAmerican Airlines
9h 04mIND-SJU
3/19Wed
2 stopsAmerican Airlines
9h 56mSJU-IND
$315
4/18Fri
1 stopDelta
5h 42mIND-SJU
4/23Wed
1 stopDelta
6h 54mSJU-IND
$325
3/19Wed
1 stopUnited Airlines
6h 05mIND-NAS
3/26Wed
1 stopUnited Airlines
9h 09mNAS-IND
$345
5/29Thu
1 stopDelta
7h 35mIND-NAS
6/3Tue
1 stopDelta
8h 37mNAS-IND
$395
3/9Sun
2 stopsUnited Airlines
21h 57mIND-NAS
3/13Thu
1 stopUnited Airlines
6h 03mNAS-IND
$459

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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.
3/11Tue
1 stopFrontier
7h 36mIND-SJU
$65
4/27Sun
1 stopFrontier
9h 12mIND-SJU
$85
3/29Sat
1 stopSpirit Airlines
11h 52mIND-STT
$94
4/4Fri
1 stopSpirit Airlines
13h 39mIND-STT
$102
3/2Sun
1 stopAmerican Airlines
9h 28mIND-NAS
$119
3/3Mon
1 stopDelta
9h 05mIND-NAS
$124
3/11Tue
2 stopsAmerican Airlines
8h 34mIND-SJU
$138
4/29Tue
2 stopsUnited Airlines
12h 37mIND-SJU
$203
4/30Wed
2 stopsUnited Airlines
12h 37mIND-SJU
$248
4/1Tue
1 stopDelta
8h 20mIND-AUA
$263

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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.
2/25Tue
multi-stop
8h 42mIND-SJU
3/3Mon
multi-stop
12h 47mSJU-IND
$218
2/25Tue
multi-stopSpirit Airlines
19h 21mIND-SJU
3/4Tue
multi-stopSpirit Airlines
23h 26mSJU-IND
$234
2/25Tue
multi-stopDelta
8h 08mIND-SJU
3/1Sat
multi-stopDelta
6h 25mSJU-IND
$275
2/23Sun
multi-stopDelta
8h 11mIND-SJU
2/28Fri
multi-stopDelta
7h 36mSJU-IND
$335
2/25Tue
multi-stopAmerican Airlines
8h 18mIND-SJU
3/4Tue
multi-stopAmerican Airlines
8h 43mSJU-IND
$360
2/23Sun
multi-stopAmerican Airlines
7h 13mIND-SJU
2/25Tue
multi-stopAmerican Airlines
8h 45mSJU-IND
$395
2/24Mon
multi-stopUnited Airlines
6h 32mIND-SJU
2/28Fri
multi-stopUnited Airlines
11h 55mSJU-IND
$425
2/23Sun
multi-stopUnited Airlines
14h 46mIND-SJU
2/27Thu
multi-stopUnited Airlines
14h 03mSJU-IND
$445
2/23Sun
multi-stopSouthwest
7h 05mIND-MBJ
2/25Tue
multi-stopSouthwest
8h 45mMBJ-IND
$536
2/23Sun
multi-stopSouthwest
8h 35mIND-AUA
2/25Tue
multi-stopSouthwest
8h 00mAUA-IND
$723

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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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