$64 Find Cheap Flights from Caribbean Islands to Indiana

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Low seasonFebruary
High seasonDecember
Cheapest flight$64
Best time to beat the crowds with an average 9% drop in price.
Most popular time to fly and prices are also 0% lower on average.
Flight from San Juan Airport to Chicago O'Hare Airport

FAQs for booking flights from Caribbean Islands to Indiana

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

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Caribbean Islands 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 Islands 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 Islands 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 Islands 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 Islands to Indiana up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • What is the cheapest day to fly to Indiana?

    Based on KAYAK data, the cheapest day to fly to Indiana is Thursday where round-trip tickets can be as cheap as $347. On the other hand, the most expensive day to fly is Monday, where round-trip prices are $482 on average.

  • What is the cheapest time of day to fly to Indiana?

    The cheapest time of day to fly to Indiana is generally at night, when round-trip flights cost $361 on average. Morning departures are around 2% more expensive than evening flights, on average. The most expensive time of day to fly to Indiana is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $399.

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

    The cheapest month for flights from Caribbean Islands to Indiana is September, when tickets cost $348 (return) on average. On the other hand, the most expensive months are March and June, when the average cost of round-trip tickets is $2,372 and $694 respectively.

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

    To get a below average price on the flight from Caribbean Islands to Indiana, you should book around 2 weeks before departure. For the absolute cheapest price, our data suggests you should book 5 weeks before departure.

  • How long is the flight to Indiana?

    An average nonstop flight from Caribbean Islands to Indiana takes 10h 17m, covering a distance of 1896 miles. The shortest route is Nassau (NAS) to Chicago O'Hare Intl Airport (ORD) with an average flight time of 3h 56m.

  • What are the most popular destinations in Indiana?

    Based on KAYAK flight searches, the most popular destination is Chicago (84% of total searches to Indiana). The next most popular destinations are Indianapolis (5%) and Louisville (4%). Searches for flights to Cincinnati (4%), to Dayton (2%) and to Fort Wayne (1%) are also popular.

Top 3 airlines serving from Caribbean Islands to Indiana

Need help choosing which airline to fly with from Caribbean Islands 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
DeltaOverall score based on 7934 reviews
7.9Comfort
8.2Boarding
7.9Entertainment
7.3Food
8.5Crew
Airline reviews

Fine except the person next to me took up her seat had raised the arm divide so she spilled into my seat. because of her size. Fortunately no one was in the seat on my right so I could use part of it.

10.0 ExcellentAnonymous, Apr 2025AMS - ATL
Read more Delta reviews

Fine except the person next to me took up her seat had raised the arm divide so she spilled into my seat. because of her size. Fortunately no one was in the seat on my right so I could use part of it.

Delta is my preferred airline. I've traveled with them for years. On time in most cases, good communication, easy to use app. Most planes are pretty nice. I was on a CRJ 700/900 however, which was pretty badly aged inside and needed a refresh. No infotainment, unreliable wifi, best to download before boarding or bring a book. Food choices are really just snacks on this flight, nice variety but about what you'd expect. Great staff and prompt in departure and early arrival too. Overall quite satisfied.

Crew was friendly Love the entertainment in the seat head rest.

Delta flight was on time, seats were comfortable, and crew was nice.

This had nothing to do with Delta… The flights were on time and flawless. The service was excellent. We purchased seats in (aisle/middle) comfort plus since this was a cross country flight. Unfortunately, the woman seated at the window was 300+ pounds and, as might be expected, covered up about a third of the middle seat also. there was absolutely nothing that Delta could have done about that… I just don’t know what the answer should be. If you purchase a seat, you should should be able to use the entire seat and not just the portion that someone else is not sitting/oozing in. Disappointing…there should be something that could be done….I'm just not sure what solution could be.

Delayed take-off. Very small plane so very scary with lots of bumps during the flight. Would never fly Delta on short flights in small 80 seaters plane again! Felt relieved when landed.

Delta is a cut above the others in customer service.

The worst part was I was NOT allowed in the lounge even though I was holding a first class ticket and have a premium American Express card. I have flown Business or First Class with many airlines. Delta is the ONLY one who does not extend this courtesy to anyone except people who hold the very expensive American Express card. As a result, I won’t fly Delta if I have any other choice.

A little bumpy ride . No food was being provided due the the turbulence. That was ok it was a short flight to my standards.

Simply outstanding. Their new lounge for Delta One customers is a cut above the rest.

Our flights got changed from United to Air Canada and our purchased seats did not get transferred so we had to pay for seats twice. I brought it up with Air Canada and they stated I had to go back and chase it with United. The united seats were $21 Canadian each and Air Canada were $56 each so we have paid $77 for each seat. Very unhappy

A bit rush for transit. Food and entertainment are not available

So far so good but food and entertainment are not available for this flight

Multiple delays and not straight answer from the United team

Stewardess spilled orange juice on my clothes/seat no help no apology just threw napkins at me to clean the mess up. Not Happy.

Smooth flight. Boarding was chaotic. Could not hear the gate agent over the intercom. People were lined up in the wrong lines. Groups one and two were told to board through line one and group 3 through line 2. All very confusing. Once in the air, the flight was smooth. There was no entertainment option on this aircraft, even though it was a larger aircraft.

The plane pushed back from the gate on time. However, it stopped on the ramp, and we waited for over 20 minutes before the aircraft pulled back to the gate. Apparently, something of importance had to be removed from the aircraft by the gate agent. I found this to be odd. The delay was not significant, but I felt that whatever was on the aircraft that had to be taken off, should’ve been done before we pushed back from the gate.

Electric plugs didn't work. Entertainment system wasn't working

The design of the light switch on the arm rest is ridiculous.

Smooth boarding process. Early departure, smooth flight, early arrival. The entertainment package has very good recent movie options. The flight crew were friendly and professional.

Paid $35 and not able to access the internet at all.

Several delays. Next flight was worse. Did not arrive home until 2am PT

Very helpful ground crew after an earlier flight delay and being rebooked on a different flight.

Everything about the flight was lovely…We left early, arrived early, cabin crew were efficient and helpful. Flight was easy and most pleasant.

First world problems, but still… We were seated in first class and asked for a cocktail on a very short, 50 minute flight. After our drink order was taken, a half hour went by, and we noticed that every other person in the small plane had been served except for us. We got up to ask about it, the drinks finally came, then were taken away three minutes later since the flight was so short. Really strange situation, on the other hand, we were in Utah.

We missed our flight. The boarding pass had the wrong gate and by the time we received the text from Kayak, our flight was already gone. I’ll never use Kayak again and will go direct to the airlines in the future.

Boarding took forever, the plane was cramped and cold, and the seatbelt song came on constantly throughout the red eye flight with a loud pre-recorded message playing each time

Cabin felt crammed Snacks are lame But crew was super efficient getting us out on time despite delay

Flight was delayed bc of mechanical issue. New plane had different configuration so some seats had to be switched. They called all passengers who needed new boarding cards. They did not call us so we thought our seats were the same and fine. When we boarded they informed us our receipts had changed and we are now all sitting separate and in the back row. Both my daughters had meltdowns and started to cry and once we got on the flight, we figured out how we could sit closer to each other, but this was very upsetting.

Took off on time and successfully avoided weather that looked to be a problem along the way

Book cheap flights from Caribbean Islands to Indiana

Recent round-trip flight deals

5/29Thu
1 stopSpirit Airlines
13h 38mSJU-ORD
6/5Thu
nonstopSpirit Airlines
4h 46mORD-SJU
$188
5/29Thu
1 stopSpirit Airlines
13h 38mSJU-ORD
6/2Mon
nonstopSpirit Airlines
4h 46mORD-SJU
$192
8/20Wed
1 stopAmerican Airlines
7h 09mSJU-SDF
8/25Mon
1 stopAmerican Airlines
6h 08mSDF-SJU
$225
5/11Sun
1 stopAmerican Airlines
7h 33mSJU-CVG
5/16Fri
1 stopAmerican Airlines
16h 07mCVG-SJU
$225
7/16Wed
nonstopFrontier
5h 08mPUJ-ORD
8/13Wed
nonstopFrontier
4h 40mORD-PUJ
$234
8/21Thu
1 stopDelta
9h 36mSJU-SDF
8/25Mon
1 stopDelta
7h 29mSDF-SJU
$255
10/2Thu
1 stopDelta
10h 09mSJU-CVG
10/7Tue
1 stopDelta
8h 30mCVG-SJU
$268
5/11Sun
1 stopFrontier
12h 30mSJU-MDW
5/16Fri
1 stopFrontier
7h 42mMDW-SJU
$298
8/20Wed
1 stopUnited Airlines
9h 33mSJU-SDF
8/24Sun
1 stopUnited Airlines
7h 44mSDF-SJU
$305
7/16Wed
nonstopUnited Airlines
5h 05mPUJ-ORD
8/6Wed
nonstopUnited Airlines
4h 42mORD-PUJ
$312

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Recent one-way flight deals

5/29Thu
1 stopSpirit Airlines
13h 38mSJU-ORD
$64
5/29Thu
1 stopSpirit Airlines
13h 38mSJU-ORD
$69
6/6Fri
1 stop
17h 41mSJU-CVG
$84
6/6Fri
1 stop
22h 10mSJU-CVG
$106
10/15Wed
1 stopAmerican Airlines
8h 40mSJU-CVG
$113
8/22Fri
1 stopDelta
6h 02mSJU-SDF
$113
6/3Tue
1 stopDelta
6h 32mSJU-IND
$113
8/20Wed
1 stopAmerican Airlines
7h 09mSJU-SDF
$133
7/3Thu
nonstopUnited Airlines
5h 05mPUJ-ORD
$141
6/11Wed
nonstopUnited Airlines
5h 05mPUJ-ORD
$149

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Last minute flights from Caribbean Islands to Indiana

Last minute flight, train and bus deals

5/5Mon
multi-stop
13h 25mSJU-ORD
5/12Mon
nonstop
4h 46mORD-SJU
$260
5/2Fri
multi-stop
7h 53mSJU-ORD
6/3Tue
nonstop
4h 46mORD-SJU
$274
5/2Fri
nonstopSpirit Airlines
5h 23mSJU-ORD
6/3Tue
nonstopSpirit Airlines
4h 46mORD-SJU
$285
5/1Thu
multi-stopSpirit Airlines
11h 55mSJU-ORD
5/6Tue
nonstopSpirit Airlines
4h 41mORD-SJU
$301
5/2Fri
multi-stopAmerican Airlines
7h 22mSJU-DAY
5/4Sun
multi-stopAmerican Airlines
16h 39mDAY-SJU
$369
5/5Mon
multi-stopAmerican Airlines
9h 13mSJU-SDF
5/10Sat
multi-stopAmerican Airlines
9h 15mSDF-SJU
$373
5/5Mon
multi-stopDelta
7h 48mSJU-ORD
5/14Wed
multi-stopDelta
8h 17mORD-SJU
$450
5/1Thu
multi-stopDelta
6h 48mSJU-SDF
5/5Mon
multi-stopDelta
7h 14mSDF-SJU
$461
5/5Mon
multi-stopUnited Airlines
15h 57mSJU-CVG
5/8Thu
multi-stopUnited Airlines
9h 44mCVG-SJU
$485
5/5Mon
multi-stopUnited Airlines
10h 40mSJU-ORD
6/2Mon
nonstopUnited Airlines
4h 51mORD-SJU
$524

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Everything you need to know for your flight to Indiana

Cabin class types available on flights to Caribbean Islands

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

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