Find flights
When to book
FAQs & Tips
Airlines
Deals

Find cheap flights from Caribbean to Indiana from $69

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 8/28. 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
0 bags
sáb. 6/29
sáb. 7/6

Search hundreds of travel sites at once for deals on flights to Indiana

In the last 7 days travelers have searched 42,686,544 times on KAYAK, and here is why:

Save 21% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Bundle and saveSave money when you bundle your flight + hotel.

Good to know

Low season

February

High season

December

Cheapest flight

$69
Best time to beat the crowds with an average 21% drop in price.
Most popular time to fly and prices are also 9% lower on average.
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 to Indiana from Caribbean 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 to Indiana with an airline and back to Caribbean 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 to Indiana from Caribbean up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top 4 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.
7.9
Caribbean AirlinesOverall score based on 186 reviews
7.6Comfort
8.3Crew
8.2Boarding
6.7Entertainment
6.7Food
Airline reviews

I was treated well in first class. I have no complaints. I will definitely fly with my favourite airline again this year.

10.0 Excellentroderick, May 2024MIA - POS
Read more about Caribbean Airlines reviews

I was treated well in first class. I have no complaints. I will definitely fly with my favourite airline again this year.

There was no music on the flights unless you came with your headset.

Their bar selection could be greatly improved; they only had one spirit option

Music would have been great and information about the flight. Meaning how high and the weather conditions.

It was good but the food was small for the duration of the flight.

I wrote to the entertainment and food OK because it was non-applicable All excellent

Checking in online still requires going on the physical check in line

I enjoyed the smooth flow and well coordinated boarding and the very courteous attitude from the cabin crew We look forward to flying with ya’ll again

Pleasant experience checking in. Seating is way too tight, especially for persons who are not petite. I thought the pilot was excellent in terms of his commentary and information. Wrong gate information on boarding passes. If I was not alert I could have lined up to board the wrong plane.

The crew was excellent, check in was easy ,the food wasn't good, movies should be recent and more selections

Overall fine but both ways for this trip was delayed.

Flight was delayed by almost 5 hours. Suitcase was not loaded despite the flight being near empty (my colleagues’ suitcases did reach JFK, unlike mine). Had to argue on phone to get JetBlue to deliver the case to my hotel. Never again

The flight was excellent. The crew was welcoming and attentive.

Great! I love Jet Blue. My favorite airline! Very efficient, clean and timely.

Run out of snack choices. Why are the seats not padded for your butt? Are we sitting on blocks of wood or metal for $250-300 a pop? This ain’t spirit. Let’s get it together people

We were told that our flight would be delayed for 90+ minutes because of weather, so we went to get something to eat only to have them randomly start boarding 15 minutes after the announcement, with no warning.

Entertainment... No earphones passed out. Many including me couldn't use the TV. Legroom was good. Crew was indifferent and a bit surly. Free wifi was a nice convenience. Check in desk location was unknown. Gate number on the boarding passes was wrong.

Going through JFK’s security is a mess. The TSA security said no shoes on the bins. So, we place our shoes in the belt and they came out all over the belt. Boarding was delayed and Flight as well.

Safe and on time were the positives. The plane wasn't cleaned before boarding, there was garbage and food on the floor and in the seat pocket. The TV screen was small and the picture fuzzy, audio quality was poor. Seatbelt was fraying and seat did not recline properly. No charging ports near the seats,

Confusing. Delay updates were out of whack At one point it said my flight was 25 hours. Three gate changes and two delays only to change back to original departure time. Gate announcer and on board flight attendant (Alejandro) making the announcements was impossible to understand due to accent and speed of speech. After beverage service the rear flight attendants sat back there on their phones. No refills no checking in, one sweep through for trash collection. Very impersonal. Bring back Coke products

Delay flight more than 8hours waiting and poor customer service!

Plane was extremely small so mind the size of your carry on

Other than lack of snacks, everything else went very well.

They don’t keep you updated on the flight status very well. It was late but nothing said

Pros: "Nothing!!! Horrible airline with horrible staff members."
Cons: "Everything. The staff and crew of Intercaribbean airlines are very unprofessional and not helpful at all. On top of the flight delays all the luggage for that particular flight was left in Kingston. Everybody was rather nonchalant and unapologetic about the situation. I was told I would get the the following day. The next day only two of my three bags showed up. I was not compensated for the inconvenience and was told point blank that they will only deliver one of my bags to my address even though they were the reason I had NONE of my luggage in the first place. They are disgusting!!! I would never recommend this airline to anyone."
Pros: "Nice people"
Cons: "A long walk to the D3 gate, but there were no amenities there I.e. snacks (to be fair a new terminal is under construction)"
Cons: "There was no air. I understand when you are on the ground it can be limited but even after getting to altitude there was no air conditioning."
Cons: "The flight was delayed for over three hours, apparently it is a regular occurence."
Pros: "almost nothing"
Cons: "The plane had a problem that forced us to turn around right after take off and as of this writing we still don’t know what’s going on or how long we are stuck here. Planes are old and apparently maintenance could be better."
Cons: "Was a bit difficult understanding the flight attendant, she had a thick Spanish accent"

I am very disappointed. I booked with kiwi when I got to the airport there was no reservation I had to purchase another ticket after my card was already charged for almost double the cost I payed through kiwi eight days after I went to their office in Tortola and they refuse to give me a receipt so that I can cancel the original payment. They said “ there is no record that you used silver to travel “ I know I did not swim to Puerto Rico . If someone can help me please so that I can cancel the payment the credit card company said I need it, I have less than 14 days or I will loose my money. This is terrible and there is no local number for them.

I booked because of time of the flights. I needed to be at my destination at a specific time, and missed my appointment because of your delays.Get rid of these junk planes. The ATR planes are dated old scary planes. And maybe you could actually be on time. This airlines on time record is horrible. The communications between the gate agents and this company dont exist.. They couldn't give any answers,. When trying to find out when the flight would leave, they get no response when they asked for details on flights, they receivedconflicting information. I felt bad for the gate agents having to deal with Silver's inability to communicate simple information. This is my last choice in air travel. On time flights are everywhere, and both flights I took were delayed. It's a sad company.

The flight itself was good and the flight attendant was very good.

It was awesome until we ran into some bad weather but the pilots did an amazing job getting us to safety and landed

If you take this airline, they WILL change the flight time, and make you miss your connection. It has happened every time I used it. It's so unreliable that I think it shouldn't be offered on Kayak. You will regret it!

In addition to the fact that Silver changed the flight time several days before the trip without offering any choices , I was sick with Covid and unable to go on the trip. I tried to ask Silver for a credit for a flight when I’d recooperated but they don’t do credits, even for illness. I will Never fly on Silver again

I canceled due to a 7 hour delay. Was forced to book another airline last minute , very expensive. Silver Aorways sucks

I spent hours with orbitz to get my tsa # on my ticket. They didn’t have a place to enter. I will never use orbitz again. No customer service. A number in which u press offered options and the message replays instead of getting customer to that area. Silver did not make the promised call back. Finally someone responded to my email and took care of it after I lost hours of my vacation arranging this. Staff on flight barked orders.

Our pilot and flight attendant, Desiree, were great. I always fly this route and this crew was better than most.

The worst flight ever; 1st and last flying to this airlines

Book cheap flights from Caribbean to Indiana

Recent round-trip flight deals

9/10mar.
nonstopSpirit Airlines
5h 14mSJU-ORD
9/17mar.
1 stopSpirit Airlines
10h 30mORD-SJU
$119
9/10mar.
1 stopSpirit Airlines
14h 36mSJU-ORD
9/17mar.
1 stopSpirit Airlines
15h 56mORD-SJU
$128
7/4jue.
nonstopFrontier
5h 17mPUJ-ORD
7/11jue.
1 stopFrontier
27h 32mORD-PUJ
$223
7/3mié.
nonstopFrontier
5h 09mPUJ-ORD
7/11jue.
1 stopFrontier
27h 32mORD-PUJ
$224
8/22jue.
1 stopAmerican Airlines
10h 23mSJU-IND
8/25dom.
2 stopsAmerican Airlines
10h 35mIND-SJU
$274
9/25mié.
1 stopAmerican Airlines
7h 51mSJU-CVG
10/6dom.
1 stopAmerican Airlines
14h 34mCVG-SJU
$276
6/12mié.
1 stopJetBlue
9h 18mSDQ-ORD
6/18mar.
1 stopJetBlue
7h 15mORD-SDQ
$490
7/1lun.
1 stopJetBlue
9h 18mSDQ-ORD
9/7sáb.
1 stopJetBlue
13h 54mORD-SDQ
$518
7/13sáb.
1 stopCopa Airlines
16h 23mSDQ-ORD
7/20sáb.
1 stopCopa Airlines
9h 35mORD-SDQ
$688
6/10lun.
2 stopsCopa Airlines
22h 17mSDQ-IND
6/28vie.
2 stopsCopa Airlines
26h 20mIND-SDQ
$868

Search by stops

Search by airline

Search by price

Recent one-way flight deals

8/28mié.
nonstopSpirit Airlines
5h 14mSJU-ORD
$69
8/21mié.
1 stopSpirit Airlines
7h 29mSJU-ORD
$72
6/5mié.
1 stopFrontier
9h 24mSJU-MDW
$98
6/4mar.
1 stopFrontier
13h 28mSJU-MDW
$103
8/29jue.
1 stopAmerican Airlines
7h 46mSJU-CVG
$115
6/4mar.
1 stopAmerican Airlines
14h 09mSJU-ORD
$133
6/14vie.
1 stopJetBlue
7h 18mNAS-ORD
$257
6/10lun.
1 stopJetBlue
14h 47mSDQ-ORD
$263
10/20dom.
1 stopCopa Airlines
10h 33mPUJ-ORD
$432
6/9dom.
1 stopCopa Airlines
10h 33mPUJ-ORD
$972

Search by stops

Search by airline

Search by price

Last minute flights from Caribbean to Indiana

Last minute flight, train and bus deals

6/3lun.
multi-stop
21h 13mSJU-ORD
6/12mié.
multi-stop
29h 18mORD-SJU
$212
6/3lun.
multi-stopFrontier
9h 53mSJU-MDW
6/6jue.
multi-stopFrontier
11h 32mMDW-SJU
$217
6/1sáb.
multi-stopSpirit Airlines
9h 00mSJU-ORD
6/12mié.
multi-stopSpirit Airlines
15h 50mORD-SJU
$235
6/3lun.
multi-stopSpirit Airlines
13h 48mSJU-ORD
6/12mié.
multi-stopSpirit Airlines
16h 45mORD-SJU
$247
5/31vie.
nonstopAmerican Airlines
5h 15mSJU-ORD
6/3lun.
multi-stopAmerican Airlines
12h 45mORD-SJU
$449
6/1sáb.
multi-stopAmerican Airlines
5h 54mSJU-SDF
6/8sáb.
multi-stopAmerican Airlines
7h 25mSDF-SJU
$474
6/4mar.
multi-stopUnited Airlines
7h 30mSJU-ORD
6/22sáb.
nonstopUnited Airlines
4h 47mORD-SJU
$489
6/1sáb.
multi-stopUnited Airlines
10h 30mSJU-ORD
7/18jue.
nonstopUnited Airlines
4h 50mORD-SJU
$494
5/31vie.
multi-stopJetBlue
14h 51mSDQ-ORD
6/1sáb.
multi-stopJetBlue
7h 50mORD-SDQ
$657
6/2dom.
multi-stopJetBlue
14h 46mSDQ-ORD
6/6jue.
multi-stopJetBlue
7h 45mORD-SDQ
$689

Search by stops

Search by airline

Search by price