$81 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 3/5. 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$311
Santo Domingo
Santo Domingo2 stops$360
Montego Bay
Montego Bay1 stop$306
Oranjestad
Oranjestad1 stop$315
Nassau
Nassau1 stop$375
Simpson Bay
Simpson Bay1 stop$395
Kingston
Kingston1 stop$334
Providenciales
Providenciales1 stop$532
Bridgetown
Bridgetown1 stop$621
Port of Spain
Port of Spain1 stop$478
George Town
George Town1 stop$528
Willemstad
Willemstad1 stop$594
St. John's
St. John's1 stop$676
Puerto Plata
Puerto Plata1 stop$525
Aguadilla
Aguadilla1 stop$372

Good to know

Low season

August

High season

March

Cheapest flight

$81
Best time to beat the crowds with an average 8% 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 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 4662 reviews
8.1Comfort
7.2Food
8.2Boarding
7.7Entertainment
8.7Crew
Airline reviews

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.

10.0 ExcellentRachel, Jan 2025TPA - MDW
Read more Southwest reviews

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.

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

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

Flight left early and arrived early. the whole trip was excellent.

Seats were really tight and the seat belts did not give enough slack.

I like in St George and prefer to fly out of CDC than SGU. Hopefully, they will continue the flights out of Cedar

Broken jer bridge. Poor communication about it. Lost 2 of 4 luggage pieces

Overall, it was okay. Seat was a little cramped. Would’ve liked more substantial snacks or opportunity to buy some.

Newer plane, relatively easy boarding, not a full flight and was told that we could not be moved up because of weight and balance issues. Otherwise, a very good experience.

Other then mechanical/ computer problem and 3.5 hours flight delay the flight was great. I guess that what happened when you fly an old airplane now a day.

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?

Maybe add a seat trade app for flyers that didn’t get seats together

It’s been awhile since I have traveled on United. I, along with my family who were on the flight noted how smoothly everything went . Boarding, flight crew and service was excellent.

The seats on this flight were almost roomy enough to be the basic amount needed for human existence. I think my favorite part of this flight was it landed at an A gate, which was the most palatial part of Sea-Tac I've ever seen - a massive improvement from the S gates.

The seats on this flight were almost roomy enough to be the basic amount needed for human existence.

There's just no way to sit fully upright and comfortably in these seats. There needs to be 2 more inches of room, and that's not something that only one person on the flight needs - the whole flight needs 2 more inches of room. If that means you sell 6 less seats, so be it. It's too close for anyone. Forcing people to pay for "premium" economy just to get "barely enough space to breathe" isn't really an answer to that.

The crew were very nice. The Chocolate is good and v there’s no entertainment. Thanks

The crew were very nice. I would have appreciated a pillow for comfort. I had a special meal that was sloppy, but the salad was great. Thanks

I liked all the informational texts. I always knew where to go and when .

Boarding is very confusing. They have Line 1 and Line 2 and many many Boarding groups. Everyone lines up under those two lines long before they call zones. If you have a higher zone 2 like I did due to a Premium Plus ticket, it’s very awkward having to ask each person which zone they have. Extremely chaotic process. On board the flight attendants had no charisma whatsoever, even to us paying extra for an upgraded cabin. I asked for a chamomile tea after dinner (as no coffee or tea was even offered) and the FÃ said they didn’t have even though listed on the drink menu. Also, the mid flight service was entirely skipped which was a soup and sandwich combo. Supposedly had a variety of snacks mid flight too but those never materialized either. A few times I walked Back there, not a single flight attendant acknowledged me as they were all deep into their iPhones. I simply Wanted a glass of water since ZERO water runs were made on this 9hr 30 min flight.

Liked the hospitality . The ight took us 6 hrs to get from fort myers to ewr.

I paid for what I got which was cheap, I brought my own entertainment. I knew what to expect, so I could be prepared. If you’re flying economy, check in early like me. I have no problems with my flight, was on time, staff were friendly, and overall good experience.

Boarded over an hour late, no communication, the sign just changed, no attendant to answer questions - she disappeared forever (hiding). Small plane and couldn’t hear the overhead nor understand.

Service in first class no longer exists on American Airlines .

Customer service in first class does not exist on American Airlines

I never have a good experience with American and this was no different. The airplane was INCREDIBLY hot. Like unbearably so. Everyone was fanning themselves with pamphlets and sweating. When someone asked the flight attendant to turn down the temperature they were told there was nothing the crew could do. Once we pushed back from the gate we then had to wait an hour to take off and the communication from the crew was not good. People were getting up this whole time and a man was even in the bathroom when we took off. Once we landed at our destination we waited another 30 minutes at the gate to deplane with, again, no communication from the crew as to what was going on.

Flight was delayed due to a steering issue with plane. The delay caused me to miss the connecting flight. The delay caused me to spend an extra 21 hours in airports and flights to get to my destination. The plane issue obviously should have been found and fixed before we even boarded. Ridiculous.

First, to be fair, the flight was on time and the trip through the air was relatively smooth. But the flight was full, and they were checking carryons. As this process went on, the crew got increasingly rude and overbearing. During the drink service, a young girl (maybe 9) who had gotten up to use the lavatory got stuck behind the cart. At some point, she started feeling fearful and overwhelmed. Passengers noticed this and asked the crew to let her return to her seat. They refused. Then she started crying, and they still refused to move the cart forward to let her sit. The poor girl was trying to be brave and compose herself. The crew handled the situation terribly and with zero grace or decency. That episode, to me, encapsulates AA’s attitude toward its passengers. Disgraceful. The plane itself was cramped and miserable, as usual. There was zero inflight media or entertainment, other than the lane and borderline inappropriate jokes the steward made during the safety briefing. Then, of course, it took the better part of an hour for the checked bags to show up at the carousel. AA is no better than the el cheapo airlines these days and a far, far cry from its former self.

This particular flight wasn't very full at the back, so there were three seats available for spreading out and getting relatively comfortable

First class flight attendant was rude and lacked any customer service skills.

Customer service for American Airlines first class is at an all time low.

Boarding was smooth and on time. Flight itself was smooth (aside from some turbulence) and no glitches. On the downside, Spirit's no-frills service was as expected (no food or drink, cramped seating, extra cost for carry-ons, etc.), the announcements were nearly incomprehensible, and the constant niggling offers of upgrades and other services for sale (wifi, sandwiches, etc.) is annoying. Overall, a pleasant and uneventful experience - definitely worth the price.

Lower cost is the reason to fly Spirit. Should give free baggage with credit card.

From gate to flight crew... All Spirit employees were great! Everyone was kind and helpful. Ride was almost smooth... A few bumps... But no problems. Seats were tight and uncomfortable. Our biggest issue was no free drinks. I can understand paying for adult beverages and can understand no snacks on a 3 hour flight... But no drinks???? I had to pay $4 for an apple juice for my son. That's not right. You should probably reconsider that.

Loved staff help @ kiosk, staff on airplane. Commitment to punctuality. I sat in a "blocked" row, where the middle seat had no passenger & loved it! I appreciate not having to pay for water, which I've experienced even on international flights. Only negative was how dirty the bathroom was for a 4.5 hrs flight. But I don't think flight attendants monitor this.

- flight attendants not very friendly. - Paid for WiFi and plane didn’t have it working , never got a refund.

Great! First time flying with Spirit and I definitely loved it!

Not efficient. Missed my connecting flight over improper operation of spirit crew.

Very difficult. Flew out on Dec 24th and it was a mess. They know it is going to be the busiest time of the year and they had no organization. Finally they called for people going on certiam flights so they could get them thru thw line then we had to rush to our gate to get in li e to board.We missed our flight do to being stuck at the border of Mexico. They would not work with us to make an affordable price so we had to wait a day with no where to go and pay 280 more for our flights. I would think that a complimentary drink would be nice. But we had to pay 4.49 for a coke. Not an overall good experience

Better service, stop treating people like cattle, have REAL FOOD for the price of the ticket. YOU ARE IN BANKRUPTCY, WAKE UP!!! ... DO BETTER, PLAN BETTER, GIVE COMFORT AND CARE TO PASSENGERS ... EARN RESPECT AND ADMIRATION, YOU'LL BE REWARDED BY THE PUBLIC.

It was good. All snacks/ drinks must be paid during flight. Bring cash with you.

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.
3/3Mon
1 stopFrontier
9h 34mIND-SJU
3/10Mon
1 stopFrontier
17h 25mSJU-IND
$140
4/15Tue
1 stopFrontier
8h 33mIND-SJU
4/23Wed
1 stopFrontier
6h 43mSJU-IND
$150
2/26Wed
1 stopSpirit Airlines
15h 37mIND-SJU
3/5Wed
1 stopSpirit Airlines
15h 33mSJU-IND
$182
2/4Tue
1 stopSpirit Airlines
8h 00mIND-SJU
2/12Wed
2 stopsSpirit Airlines
26h 39mSJU-IND
$186
2/26Wed
1 stopDelta
10h 39mIND-SJU
3/5Wed
1 stopDelta
6h 25mSJU-IND
$275
2/20Thu
1 stopDelta
10h 39mIND-SJU
2/26Wed
1 stopDelta
10h 39mSJU-IND
$295
2/5Wed
1 stopAmerican Airlines
15h 10mIND-SJU
2/8Sat
1 stopAmerican Airlines
15h 56mSJU-IND
$330
2/19Wed
1 stopUnited Airlines
9h 06mIND-SJU
2/25Tue
2 stopsUnited Airlines
11h 55mSJU-IND
$331
5/16Fri
1 stopAmerican Airlines
15h 59mIND-SJU
5/21Wed
1 stopAmerican Airlines
7h 56mSJU-IND
$337
2/4Tue
1 stopUnited Airlines
8h 51mIND-SJU
2/7Fri
2 stopsUnited Airlines
11h 46mSJU-IND
$365

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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.
3/5Wed
1 stopSpirit Airlines
6h 17mIND-SJU
$81
2/3Mon
2 stopsSpirit Airlines
14h 49mIND-SJU
$98
2/8Sat
1 stopDelta
4h 23mIND-NAS
$134
4/5Sat
1 stopAmerican Airlines
6h 29mIND-SJU
$138
6/15Sun
1 stopAmerican Airlines
15h 37mIND-MBJ
$182
4/22Tue
1 stopUnited Airlines
6h 11mIND-MBJ
$227
7/15Tue
1 stopDelta
7h 51mIND-STT
$232
5/25Sun
2 stopsUnited Airlines
23h 43mIND-MBJ
$247
2/2Sun
1 stopSouthwest
8h 30mIND-SJU
$253
2/14Fri
2 stopsSouthwest
10h 30mIND-SJU
$388

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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.
1/26Sun
multi-stopSpirit Airlines
22h 44mIND-SJU
2/1Sat
multi-stopSpirit Airlines
13h 20mSJU-IND
$287
1/25Sat
multi-stop
17h 44mIND-SJU
2/1Sat
multi-stop
13h 20mSJU-IND
$304
1/26Sun
multi-stopSpirit Airlines
22h 44mIND-SJU
2/1Sat
multi-stopSpirit Airlines
23h 16mSJU-IND
$320
1/25Sat
multi-stopAmerican Airlines
10h 25mIND-SJU
1/28Tue
multi-stopAmerican Airlines
10h 51mSJU-IND
$335
1/25Sat
multi-stopAmerican Airlines
8h 28mIND-SJU
2/1Sat
multi-stopAmerican Airlines
7h 18mSJU-IND
$348
1/25Sat
multi-stopUnited Airlines
7h 15mIND-SJU
1/27Mon
multi-stopUnited Airlines
11h 46mSJU-IND
$380
1/26Sun
multi-stopUnited Airlines
10h 02mIND-SJU
1/31Fri
multi-stopUnited Airlines
11h 46mSJU-IND
$442
1/24Fri
multi-stopDelta
7h 35mIND-MBJ
1/29Wed
multi-stopDelta
7h 10mMBJ-IND
$476
1/24Fri
multi-stopDelta
7h 35mIND-NAS
1/29Wed
multi-stopDelta
8h 53mNAS-IND
$487
1/24Fri
multi-stopCopa Airlines
15h 53mIND-MBJ
1/29Wed
multi-stopCopa Airlines
22h 07mMBJ-IND
$1,150

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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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