$114 Find Cheap Flights from Caribbean to Indiana

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Caribbean to Indiana departing on 8/20. 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, 0 bags

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Low seasonMarch
Cheapest flight$114
Best time to beat the crowds but there is an average 22% increase in price.
Flight from San Juan Airport to Chicago O'Hare Airport

FAQs for booking flights from Caribbean to Indiana

  • How does KAYAK find such low prices on flights from Caribbean to Indiana?

    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 Caribbean to Indiana.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Caribbean to Indiana?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Caribbean to Indiana 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 Caribbean to Indiana?

    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 Caribbean to Indiana 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 Caribbean to Indiana?

    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 Caribbean to Indiana up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • How many airports are there in Indiana?

    There are 5 airports in Indiana. The busiest airport is Indianapolis Airport (IND), with 74% of all flights arriving there.

  • What is the cheapest flight to Indiana?

    The cheapest ticket to Indiana from Caribbean found in the last 3 days was to Indianapolis, at $494 round-trip. The most popular route is Punta Cana (PUJ) to Indianapolis (IND) and the cheapest round-trip airline ticket found on this route in the last 3 days was $494.

  • What is the cheapest month to fly from Caribbean to Indiana?

    The cheapest month for flights from Caribbean to Indiana is September, when tickets cost $341 (return) on average. On the other hand, the most expensive months are May and January, when the average cost of round-trip tickets is $796 and $709 respectively.

  • How far in advance should I book a flight from Caribbean to Indiana?

    To get a below average price on the flight from Caribbean to Indiana, you should book around 2 weeks before departure, which saves you about 22% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 19 weeks before departure.

  • How long is the flight to Indiana?

    An average nonstop flight from Caribbean to Indiana takes 11h 27m, covering a distance of 1910 miles. The shortest route is Nassau (NAS) to Chicago O'Hare Intl Airport (ORD) with an average flight time of 3h 53m.

  • What are the most popular destinations in Indiana?

    Based on KAYAK flight searches, the most popular destination is Chicago (81% of total searches to Indiana). The next most popular destinations are Indianapolis (11%) and Cincinnati (3%). Searches for flights to Louisville (2%), to Dayton (1%) and to Fort Wayne (1%) are also popular.

Reviews of the top 5 airlines serving from Caribbean to Indiana

 
Need help choosing which airline to fly with from Caribbean to Indiana? 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 4262 reviews
8.6Crew
7.5Entertainment
8.0Comfort
8.1Boarding
7.0Food
Airline reviews

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

4.0 OkayAnonymous, May 2026
MDW - LAX
Read more Southwest reviews

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

The flight was smooth. The Southwest experience has degraded overall, but this one was okay.

No gluten free snacks. Seats felt worn or bare bones even though it was a new 737 MAX 8.

One major problem that was very unprofessional and uncalled for. Plane landed and we had to wait 20 minutes to get off the plane since they were waiting for someone to come to the gate to drive the jetway. Southwest couldn't have someone available and waiting for the plane to land? Is there only one person in Hobby airport who knows to drive the jetway? Was he at lunch? In the bar? Uncomfortable and uncalled for!

The checking experience in Orlando was terrible, almost missed the flight. Too many travelers and Southwest completely understaffed.

I'm glad it wasn't only 75% full because I could get a good seat

if I was good. Not happy that I have to pay extra money to get the seat I need for lake room, but I guess that’s a sign of the times.

Seats were very comfortable. They tilted back. Drinks and snacks were free and served 3 times. Attendants were awesome.

Plane was clean and comfortable. Flight attendants and gate staff were professional, friendly and efficient. Boarding and deplaning were orderly and efficient. All in all, the typical excellent Southwest experience.

Truly terrible. Will never willingly fly southwest again. Seats are worse than before they switched to assigned seating. One flight attendant was the opposite of helpful (rude, unhelpful, dismissive, and as my stranger seatmate said unprompted: a total prick). This caused me, 15 minutes into the flight, to book an alternate return flight home on a competing airline (first class 1.2k purchase instead of my existing planned flight) just so I would not have to ever be on that aircraft, with that terrible service person, with those horrific seats ever again.

Great flight with a terrific crew. Uneventful and early arrival. Thank you.

No service flight that took 5 hrs and a stop at an unscheduled airport. Crew and pilots did their jobs

Clean planes and not take my comfort class seat away.

Weather caused a long delay, but the efficiency and updates from the pilot were helpful. We were able to make our connection fortunately.

Flight was delayed. Then eventually cancelled. The female staff that was announcing overhead was unprofessional. She was telling everyone that the company is not going to give any money for taxi, hotel etc. then eventually the flight was cancelled.

My service light was on 15 minutes before I had to get up and find a glass of ice. And I was in business class. The meals were not for either my wife and I. She did not eat the entire 10 hour flight and I managed a bowl of soup. I was expecting much more from business with what we paid.

Planes were clean, no water or snacks on either flight.

Free & relatively fast Wi-Fi. Would've liked a wider drink selection.

I continue to be satisfied with Delta’s excellent service out of LGA. The digit id works well and gets me through security in no time. Whenever possible, I choose Delta.

Was revoked with Jet Blue due to delay from Kenya Air

These airplanes should be illegal. The seats are two tight, it is a safety issue. Wheelchair support was ridiculously slow. We almost missed our flight.

It was a short flight so I was expecting too much

Horrifying Almost 2 million miles. Bring your own food and drink. One coffee or drink every three hours. Have to order meals on app more than 24 hours ahead Tiny and dirty bathrooms

Flight was delayed but more than 90 minutes. This caused me to miss my available windows for pick-up by a friend. I had to pay $125 for an uber back home from the airport which was an added expense that I had not budgeted for my trip. Staff was friendly.

Uncomfortable plastic seats even in premium economy. No free wifi. Even paid wifi was spotty to nonexistent. Bad food. Much worse than economy on foreign carriers like Qantas.

How can you rate a flight when it is canceled after you leave the gate & 3 hours into sitting there or in remote area of airport after mechanical problems

Seat pitch is horrible especially on the 15 hour flight. Gate crew at SFO was Outstanding. The flight crew was also great.

Had a one hour delay due to mechanical issue. I didn’t think I’d be able to make my connecting flight, but they waited for me and greeted me when I arrived to help things run smooth.

Broken tray table. Erratic service. Premium economy is more economy than premium- other airlines treat PE much better. No lounge access.

6 1/2 hours from Tampa to SFO on a Boeing 737. Cramped. No Service. No real food. One pass for coffee at the beginning and a second pass THREE hours later. And check-in in Tampa was nasty even by United standards. And I am at almost TWO million miles on United. It's a non-stop. But terrible service.

Was put into a seat right behind the toilet that had no entertainment possible but did have plenty of leg room over noisy part of plane.

The passport line was so long that many of us were concerned about missing our flight and some did. It would've helped if a AA representative had gone to the passport check-in sooner to advise that boarding was closing and those flying that were stuck back in the line, needed to come forward with apologies to others. An AA representative did do that but only after boarding had already closed. (They delayed take-off so that more who were running with carry-ons could get to the gate - especially stressful for older people!) Then to be crammed into a seat with barely enough leg room for a thin woman, 5'7", like me, much less for a taller, bigger person was not comfortable, especially if the person in front decided to lean back. Crew was fine, food and entertainment also.

Movies on my phone are great. It would be nice to have a gluten free snack option.

It was what i expected. I like the movies you can access from your phone. It would be nice if there was a gluten free snack offered. But I did bring my own snack knowing there would not be a gluten free option

The flight was peaceful, just s slight turbulence, pilots and crews were all nice and made a great job! Arrived safely in the Philippines. Thank you ya’ll!

Ontario airport boarding was very easy to park and access, is clean and TSA took 10 minutes total. Check-in was a breeze and cruise was very nice.

American Airlines II: Delay Boogaloo. Multiple gate changes, delays, boarded and then MORE delays. I hate to say this won’t matter, but posting stuff about major corporations in 2026 is a post-modern “scream into the void.” Was multiple hours late coming home, so there you go.

Awful, tons of delays, I got into Chicago multiple hours late meaning I hit the very traffic I tried so desperately to avoid. Just empty apologies from American Airlines text alerts. Trash behavior from a trash airline.

The flight attendants were very friendly, efficient, and helpful. The plane was ahead of schedule, and it all went very smoothly. Thank you.

They lost my baggage and I am still struggling to the information and update

My flight today was cancelled because it was Spirit Airlines but have received no refund.

THEY WENT OUT OF BUSINESS AND CANCELED FLIGHT. REPLACEMENT FLIGHTS WERE 300% HIGHER SO MY FAMILY COULD NOT GET TOGETHER. WHY AM I GETTING THIS SURVEY?????

If there WAS a flight it would have been EXCELENT..Maybe?

It would have been better IF IT HAD NOT BEEN CANCELED!!!!

There was no flight. Spirit went bankrupt Right before my departure and kayak did not refund me any money. I would like my refund kayak. How can I get it? Please let me know. Thank you

Flights were canceled due to airline shutting down and haven’t received a reimbursement. Had to book last minute new flights which were expensive

My flight was canceled the morning of the flight. I had to rebook a flight with a different airline that cost me $900 out of my pocket

Had a flight change had to get a credit.will I get my money back.

Shut down without prior notice End up with spending lots of extra $$$

There was a crack in my window seal. And Spirit is now closed forever.

Everything you need to know for your flight to Indiana

Cabin class types available on flights to Caribbean

Cabin classes available on flights to Caribbean. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.