$106 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 4/18. 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

KAYAK searches hundreds of travel sites at once for deals on flights to Caribbean Islands

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Indianapolis to Caribbean Islands.
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Indianapolis to Caribbean Islands.
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Cheap Flights from Indianapolis to Caribbean Islands

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana1 stop$382
Santo Domingo
Santo Domingo1 stop$387
Montego Bay
Montego Bay1 stop$352
Oranjestad
Oranjestad1 stop$423
Nassau
Nassau1 stop$378
Kingston
Kingston1 stop$489
Simpson Bay
Simpson Bay2 stops$438
Providenciales
Providenciales2 stops$341
Port of Spain
Port of Spain1 stop$563
Bridgetown
Bridgetown1 stop$568
George Town
George Town1 stop$337
Willemstad
Willemstad2 stops$687
Puerto Plata
Puerto Plata2 stops$593
St. John's
St. John's2 stops$737
Aguadilla
Aguadilla1 stop$212
Punta Cana
Punta Cana1 stop$382
Santo Domingo
Santo Domingo1 stop$387
Montego Bay
Montego Bay1 stop$352
Oranjestad
Oranjestad1 stop$423
Nassau
Nassau1 stop$378
Kingston
Kingston1 stop$489
Simpson Bay
Simpson Bay2 stops$438
Providenciales
Providenciales2 stops$341
Port of Spain
Port of Spain1 stop$563
Bridgetown
Bridgetown1 stop$568
George Town
George Town1 stop$337
Willemstad
Willemstad2 stops$687
Puerto Plata
Puerto Plata2 stops$593
St. John's
St. John's2 stops$737
Aguadilla
Aguadilla1 stop$212

Book Cheap Indianapolis to Caribbean Islands Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Indianapolis to Caribbean Islands that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Indianapolis to Caribbean Islands

Thu, Apr 16 - Thu, Apr 23
Multiple Airlines Logo
12:17 pm - 2:01 am
IND
-
SJU
13h 44m
2 stops
Multiple Airlines Logo
7:45 am - 12:51 pm
SJU
-
IND
29h 06m
1 stop
$253Multiple Airlines
Sat, Apr 11 - Tue, Apr 14
Multiple Airlines Logo
5:08 pm - 11:49 am
IND
-
SJU
18h 41m
2 stops
Multiple Airlines Logo
6:30 am - 11:11 am
SJU
-
IND
28h 41m
1 stop
$255Multiple Airlines
Wed, May 6 - Thu, May 14
Delta Logo
6:00 am - 11:45 am
IND
-
SJU
5h 45m
1 stop
Delta Logo
5:43 pm - 12:33 am
SJU
-
IND
6h 50m
1 stop
$270Delta
Tue, May 19 - Tue, May 26
American Airlines Logo
6:05 am - 1:49 pm
IND
-
SJU
7h 44m
1 stop
American Airlines Logo
12:59 am - 9:14 am
SJU
-
IND
8h 15m
1 stop
$277American Airlines
Fri, Apr 10 - Wed, Apr 15
Delta Logo
6:00 am - 2:48 pm
IND
-
STT
8h 48m
1 stop
Delta Logo
1:59 pm - 12:41 am
STT
-
IND
10h 42m
1 stop
$280Delta
Mon, May 11 - Fri, May 15
American Airlines Logo
7:15 pm - 12:35 pm
IND
-
STT
17h 20m
1 stop
American Airlines Logo
5:05 pm - 11:59 pm
STT
-
IND
6h 54m
1 stop
$300American Airlines
Mon, Apr 13 - Fri, Apr 17
United Airlines Logo
7:00 am - 4:05 pm
IND
-
PLS
9h 05m
2 stops
United Airlines Logo
5:15 pm - 10:22 am
PLS
-
IND
17h 07m
1 stop
$341United Airlines
Sat, Apr 11 - Sat, Apr 18
Spirit Airlines Logo
5:45 am - 3:28 pm
IND
-
STT
9h 43m
1 stop
Spirit Airlines Logo
12:25 pm - 11:59 pm
STT
-
IND
11h 34m
1 stop
$352Spirit Airlines
Sat, Apr 11 - Sat, Apr 18
Spirit Airlines Logo
5:08 pm - 1:26 pm
IND
-
STT
20h 18m
1 stop
Spirit Airlines Logo
10:49 am - 11:58 pm
STT
-
IND
13h 09m
1 stop
$353Spirit Airlines
Fri, Jun 5 - Mon, Jun 8
United Airlines Logo
7:00 am - 1:30 pm
IND
-
MBJ
7h 30m
1 stop
United Airlines Logo
4:12 pm - 10:13 am
MBJ
-
IND
17h 01m
1 stop
$372United Airlines
Booking Insights

KAYAK's insights & trends for Indianapolis to Caribbean Islands flights

Get data-powered insights and trends into flights from Indianapolis to Caribbean Islands to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Indianapolis to Caribbean Islands flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to Caribbean Islands from Indianapolis found in the last 72 hours was to San Juan, at $520 round-trip. The most popular route is from Indianapolis (IND) to Punta Cana (PUJ), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $544.

Can I save money by flying with a layover from Indianapolis to Caribbean Islands?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $384, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Indianapolis to Caribbean Islands?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Indianapolis to Caribbean Islands, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Indianapolis to Caribbean Islands is September, when tickets cost $269 (return) on average. On the other hand, the most expensive months are December and March, when the average cost of round-trip tickets is $635 and $452 respectively.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Indianapolis to Caribbean Islands, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Indianapolis to Caribbean Islands, you should book around 2 weeks before departure, which saves you about 20% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 10 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$106
Best time to beat the crowds with an average 18% drop in price.
Most popular time to fly with an average 7% 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.

Reviews of the 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.
8.0
SouthwestOverall score based on 4319 reviews
8.1Boarding
7.0Food
8.0Comfort
8.6Crew
7.5Entertainment
Airline reviews

Boarding was easy. The seats are small and fairly uncomfortable

8.0 ExcellentNicole, Mar 2026
LGB - OAK
Read more Southwest reviews

Boarding was easy. The seats are small and fairly uncomfortable

I was supposed to be on a later flight. When I showed up at the gate, the woman working there was extremely helpful getting moved up to this earlier flight.

We had a 5 hour delay on the tarmac in Baltimore

Long layover between flights to Long Island from BWI - need better coordination between flights

I elected to pay for the upgrades and found very little difference

The new seating arrangement is so over priced for what you get.

The problem with the seat assignments is that there were a lot of rows in the front that were empty but my row at the back was full. Just not so pleasant.

No food or entertainment, just a quick 40 minute flight. A little bumpy due to Santa Ana winds but pilot has no control over that. Good flight and landing!

Good but I prefer choose your own seat. With the new assigned seats they should board from the back I see no advantage to this new boarding. Just like every other airline

I realize they are still working out kinks with the new boarding process, but by the time I boarded in group 5, most of the bins were full. All airlines should better enforce small bags and jackets going under the seats until everyone has boarded.

My flight was canceled on Sunday. Rebooking took three hours. Had to pay for accommodations another night. New flight was delayed for 5 hours, all that was sent was a 12 dollar food voucher, which doesn’t tell you how to use it. Then when we landed we had to sit on the plane for an hour before we could get off.

Miserable. This entire round trip was miserable. I booked evening flights to and from Detroit on consecutive days that should have had me at my destination by 10:30. Instead I arrived after 3am on my flight to Detroit and after midnight on my return. Multiple unforced errors like awaiting bags to get put on the plane for almost an hour in Detroit and a 20 minute delay to pull up to the gate in Atlanta has me rethinking my assumption that delta is the best and most reliable airline

Perhaps when you’re sitting in 1st class and the crew closes the bathroom for the pilots, there could be a notification other than holding your hands up as a blockade when you get there and you’re told the restrooms are closed please turn around … especially at night when visibility is poor and you’re met by a flight attendants with their arms up

First class is comfortable. Enjoyed a movie and was able to relax compared to coach.

Loved flying First Class. Very comfortable. The seat was amazing. Enjoyed a movie and was able to relax so much better than in coach.

We landed and sat on the tarmac for 45 minutes because they only have one gate at the airport and there was another plane running late so we had to wait

The WiFi was not working. That made for a long flight.

With Aeromexico it ended up good but with Delta it was bad because we did everything through Delta... Showed up at the Delta terminal... It was the wrong place! Nothing ever told us to go to the Aeromexico terminal. It said "in partnership with Aeromexico" but I was never instructed to check in with them or go to their terminal. We had to haul @$$ running through the airport and almost didn't make it thanks to this poor communication. 👎🏽

Absolutely no communication on why there's a delay and multiple flight time reschedules. I would have canceled the flight and drove back home if I known it was going to be rescheduled 3 or 4 times.

Another late night flight and MORE men belligerently drinking and yelling. I had to move from first to economy because they were so obnoxious and disruptive. Crazy to go from a cozy chair to cardboard when you were supposed to be in first. Delta allows was too much drinking which leads to belligerent behavior.

OK, we were delayed and had to de plane and reboard.

United is one airline which regardless of how many separate United tickets in existence, if one flight breaks down, the airline will take care of all the flights.

Both our flights were delayed. Almost didn’t get in the second flight. Staff was rude to the bone.

Both my flight where delayed Had 25min to make it to my transfer flight

Everything was on time and service on the flight was great!

Wifi Bluetooth features for watching in flight movie was horrible. Screen kept blacking out no connection of sound although it said connected. Other than that smooth trip .

The 777’s economy seat’s legroom was more tolerable than expected. I appreciate the reclining mechanism which slides the seat forward to minimize cannibalizing the space behind. The food was terrible: very salty.

The travel company that you have on your site did me so wrong. I don’t know how it happened, but they put my son‘s name on my plane ticket flying to Vietnam. Along with his birthday. They would not have let me fly from Fort Myers to Ho Chi Minh City. I don’t think that I can ever use your service again. I typed my information into the browser along with my passport number and four days before I’m leaving I have to quickly search another ticket to fly out here.

Seats are uncomfortable. This has been a trend in the industry for decades. Trying to fit more seats on each plane to increase profits at the expense of the passenger.

The flight was delayed so we were dead tired, and after that the turbulence was horrible. I was very scared.

Really good. I accidentally left my duffel on the plane and the reps were so friendly in retrieving it.

My 9:50AM flight was delayed to 3:40PM "due to incoming aircraft delay". No aircraft is "delayed" that long. Found out once we did board (after several changes in times) that the aircraft had a maintenance issue and we had to wait for another aircraft. Just tell us that. The aircraft we did get was old and the seats need to be updated. I have been traveling for several weeks with AA and you should refresh your entertainment content as frequent flyers have gone through most of your new content. I have Celiac and a shellfish allergy and continue to have struggles with meals on business and first class flights. Please keep this in mind. Sorry - was a long travel day yesterday and a bit cranky this morning with my experience comments. Still an AA fan.

The business steward was absolutely amazing! Smiles and kindness! Wish all AA flights are like this one!

As a first class customer, there was no power the entire flight which limited my ability to work. I find this unacceptable. The first 11 rows on the left side of the plan were out. I was only offered the option to charge my phone which was not the issue because my laptop was out of power. I asked if there was anything that can be done for me, and the answer was, "no". I was not offered any type of compensation for this AA problem which caused me unnecessary stress due to inability to address business issues on an already challenging travel day. Flight attendants tried to reset the power once but that was the extent of their support. Very disappointing for the lack of expected services on a flight. Please contact me with customer focused response to this complaint.

Not really sure I enjoyed the flight at all. The flight attendants seemed a little tired and rude at times. The snacks were lacking in taste and sustenance. The flight was incredibly turbulent for three plus hours and the pilot had to do a second pass to land at our final destination because he was coming in so fast. He must have taken a short cut and because of it we had to suffer the violent turbulence and the dropping down. It had to be one of if not the worse flights I have ever been on and have traveled vastly all over the world.

Delay after delay with little communication then AA lost my luggage and at airport would not assist just said scan this QR code to track your luggage and submit a claim. However QR code provided did not work so have to go back to airport

After changing the departure gate 5 times making us mo e from one side of the airport to the other and then back the flight was delayed nearly 2 hours. The male flight attendant had a bad attitude with the guest being condescending, disrespectful with people who were already on edge.

Easy boarding. Rows are smaller but that may be an older and bigger me now :)

It would have been nice if American tried to care.

American Airlines did everything they could with the high Spring Break crowd. I was frustrated to be changed from 1st class to a middle seat at the back of the plane. This has happened before, not sure booking 1st class and paying the extra actually works.

Delayed 11 hours with two being on our destinations tarmac, no compensation or refund and was told I would actually get charged a $200 cancellation fee if I decided to switch airlines for my return flight. For their inconvenience they gave a $10 meal voucher to split between two people in a airport.

Absolutely terrible, flight was cancelled and we missed our cruise. Will never fly Spirit again.

Horrendous and unprofessional staff and will never fly spirit again

Like Spirit but bad that you have to pay for water 🙃

My flight was ultimately cancelled but the lack of updates and professionalism from the crew leading up to the cancellation announcement was frustrating for all passengers.

Delay due to personnel issues on Spirit’s end. Original departure time 9:30pm. Took off at 2:15am. Lost an entire night’s sleep bc Spirit couldn’t get a crew together. Very poor.

Sadly the flight was delayed by 4 hours due to the weather snd sir traffic control staffing. Otherwise the crew was amazing and the flight was perfect.

If there are delays, it takes less than a minute for a Spirit employee to make an announcement. It’s very simple.

I’m still waiting to get on the flight. No one knows what’s happening. The passengers have gotten no updates. We have been up all night and waiting at the airport. This is no way to operate and we should be refunded for this lack of respect for their passengers.

Not enough crew members so we had to wait for more to arrive and they could never give us updates timing. Not even water for free on board. Bare bones airplane- there wasn’t even a seat back pocket to put things into. Spirit is cheap for a reason but this was dismal

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports