$88 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 4/25. 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$272
Santo Domingo
Santo Domingo1 stop$336
Montego Bay
Montego Bay1 stop$352
Oranjestad
Oranjestad1 stop$313
Nassau
Nassau1 stop$378
Kingston
Kingston1 stop$437
Simpson Bay
Simpson Bay1 stop$377
Providenciales
Providenciales1 stop$353
Port of Spain
Port of Spain1 stop$624
Bridgetown
Bridgetown1 stop$653
George Town
George Town2 stops$354
Willemstad
Willemstad1 stop$658
Puerto Plata
Puerto Plata1 stop$573
St. John's
St. John's2 stops$737
Aguadilla
Aguadilla1 stop$176
Punta Cana
Punta Cana1 stop$272
Santo Domingo
Santo Domingo1 stop$336
Montego Bay
Montego Bay1 stop$352
Oranjestad
Oranjestad1 stop$313
Nassau
Nassau1 stop$378
Kingston
Kingston1 stop$437
Simpson Bay
Simpson Bay1 stop$377
Providenciales
Providenciales1 stop$353
Port of Spain
Port of Spain1 stop$624
Bridgetown
Bridgetown1 stop$653
George Town
George Town2 stops$354
Willemstad
Willemstad1 stop$658
Puerto Plata
Puerto Plata1 stop$573
St. John's
St. John's2 stops$737
Aguadilla
Aguadilla1 stop$176

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

Mon, Apr 13 - Thu, Apr 16
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
$249Spirit Airlines
Tue, Apr 14 - Sat, Apr 18
Multiple Airlines Logo
12:07 pm - 2:01 am
IND
-
SJU
13h 54m
1 stop
Multiple Airlines Logo
12:57 pm - 11:58 pm
SJU
-
IND
11h 01m
2 stops
$258Multiple Airlines
Fri, Jun 5 - Wed, Jun 10
Frontier Logo
1:46 pm - 2:08 am
IND
-
SJU
12h 22m
1 stop
Frontier Logo
4:05 pm - 6:56 pm
SJU
-
IND
26h 51m
1 stop
$264Frontier
Mon, May 4 - Tue, May 12
Frontier Logo
12:34 pm - 2:24 pm
IND
-
PUJ
25h 50m
1 stop
Frontier Logo
3:35 pm - 11:23 am
PUJ
-
IND
19h 48m
1 stop
$272Frontier
Wed, Apr 15 - Thu, Apr 23
Delta Logo
7:05 am - 2:48 pm
IND
-
STT
7h 43m
1 stop
Delta Logo
3:05 pm - 12:41 am
STT
-
IND
9h 36m
1 stop
$280Delta
Sat, May 2 - Sat, May 16
Delta Logo
6:13 am - 11:33 am
IND
-
MBJ
6h 20m
1 stop
Delta Logo
4:59 pm - 12:33 am
MBJ
-
IND
6h 34m
1 stop
$352Delta
Mon, May 18 - Fri, May 29
American Airlines Logo
7:43 pm - 11:31 am
IND
-
GCM
16h 48m
2 stops
American Airlines Logo
5:12 pm - 10:33 am
GCM
-
IND
16h 21m
2 stops
$354American Airlines
Sat, May 2 - Sat, May 16
American Airlines Logo
7:43 pm - 12:13 pm
IND
-
MBJ
17h 30m
1 stop
American Airlines Logo
10:13 am - 12:32 am
MBJ
-
IND
13h 19m
2 stops
$357American Airlines
Fri, Apr 17 - Thu, Apr 23
United Airlines Logo
8:07 pm - 12:30 pm
IND
-
GCM
17h 23m
2 stops
United Airlines Logo
1:35 pm - 9:32 pm
GCM
-
IND
6h 57m
1 stop
$366United Airlines
Sat, May 2 - Sun, May 10
United Airlines Logo
7:15 am - 3:10 pm
IND
-
MBJ
8h 55m
2 stops
United Airlines Logo
4:12 pm - 10:05 am
MBJ
-
IND
16h 53m
2 stops
$377United 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 $372 round-trip. The most popular route is from Indianapolis (IND) to San Juan Luis Munoz Marin Intl Airport (SJU), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $372.

What is the cheapest time of day to fly to Caribbean Islands?

The average price for all round-trip flights from Indianapolis to Caribbean Islands depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to Caribbean Islands is generally in the morning, when round-trip flights cost $552 on average. The most expensive time of day to fly to Caribbean Islands is generally in the morning, which is peak travel time and where the average cost of a ticket is $552.

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 $375, 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$88
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 4333 reviews
7.5Entertainment
8.1Boarding
8.0Comfort
8.6Crew
7.0Food
Airline reviews

I have roller bag with food and medication told me I couldn't bring on my 2nd flight today. 15 years flying with SW never an issue with that bag.

2.0 MediocreStuart, Mar 2026
HOU - STL
Read more Southwest reviews

I have roller bag with food and medication told me I couldn't bring on my 2nd flight today. 15 years flying with SW never an issue with that bag.

Southwest continues to do less for more money. Flight attendants used to be fun and friendly. But now it’s like they don’t even see you. Such a shame.

Great flight. Good snacks and drinks. Grateful it was free. The flight from Nashville to louisville, i think her name was Tracy (not sure that's right) super awesome, nice and cheerful. She really enjoyed being at work today! She was the person who scanned the boarding pass on flight wn941. She should be recommended for a raise !

I liked it better when you were truer to your roots Am paying more for less fun

Southwest was greaat! The most expensive but the least upsetting for those we were flying to see.

I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.

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

The flight was delayed 90 minutes The Gate was wrong The Restroom on Aircraft was not clean There was a half used water bottle in my seat

Delta is always a wonderful experience. A clean plane and the crew is really friendly.

Too many people are taking up space in the overhead bins with their extra piece of luggage. Since they cannot fit their backpacks or extra luggage piece under the seat in front of them, they store it in the overheads and thus taking up room for other passengers. It wasn’t only one or two persons; more like 12 or 13 passengers.

Excellent service, I love the soft blush pink mood lighting on the 767-400ER during meal service. The overhead gasper vents on the 767-400ER were also very strong with a lot of airflow to keep me comfortable on my flight.

This was the worse experience. They delayed our flight twice and we still had to find another flight to get home sooner which was alos delayed. Also, the flight attendant named Ginny on DL9890 leaving at 4:13pm on 3/23/26 was extremely rude.

I love Delta the flight attendants were personable and the flight arrived 1/2 earlier thanks expected. All a plus. The gate agent was a bit flustered but even with that I still had a good experience. Her supervisor assisted me.

Got to fly my favorite plane, the Boeing 767-400ER, to Milan. The soft blush pink mood lighting during meal service was very beautiful and gorgeous. The service was top-notch, and our flights were on time. I highly recommend Delta.

I am still at the Airport! Delayed Delayed and Delyaed

I took seat 15A in anticipation of window seat, there is no window.

The first class flight attendant was awful to everyone. Very rude; no customer service. She should not be working in first class.

the entire flight felt off. The crew seemed uninterested and disengaged. The food service was really bad - overcooked, bland, weird food service. They actually woke us up to serve chicken wraps in the middle of the night, after dinner and before breakfast. Made no sense. Ultimately, I was glad they did though, because the breakfast had been held for so long it was inedible. Eggs, potatoes, sausage - all disgusting. We were asked to "honor" the lavatories for premium customers and stay in our own cabin: this was also strange. So people in economy didn't pay enough to use the closest toilet to them??? It's a toilet. All in all, not the experience I have come to expect from United Airlines. The return flight from Paris to SFO was better, btw.

Smooth and easy boarding, comfortable for the entire 5 hour flight, and the seat back entertainment was great! I appreciated all the features, from location info and maps, movies, the ability to connect with Bluetooth headphones, and good selection of movies. Food was good, normal airline snacks (I didn’t purchase anything)

Overall, the flight was good. Lounge access should be with all business class tickets.

They promise free wi-fi prior to boarding and then once on board you are informed you have to purchase wifi even after being a mileagePlus member.

I've been flying American mostly, and it's been very frustrating. This united flight makes me realize maybe the issue isn't flying, but the airline. United was a significantly better experience. The plane was more comfortable, with a normal amount of leg room (vs the ridiculous reductions AA has made), more comfortable seats, screens to watch movies. It was a much better experience!

Awful. No counter attendants. No dinner offered due to delays.

Horrible service no Wi-Fi connection on both leg of the flight and they are refusing to fix bad service

3 hour delay…. Nearly 2 hours sitting on tarmac. Do better, United. Or at least have the sense to not say “we hope you enjoyed your flight with us” upon disembarking.

Flights were on time. Free Wifi on plane. Everything was well organized.

During landing. 2 crew members passed 3 times by my lane and didn't notice that people in front of us had their site to the furthermore reclined... That was uncomfortable and could have been dangerous.

The flight itself was excellent but the gate attendant made me check my carryon since she said it was an inch too big. I’ve had no problems with this carryon on recent flights on Qantas, Delta, Austrian, Southwest Airlines even though the overhead bins are the same size. there were other carryons in the bins that also looked larger than mine and there was room left in the bins for more. When I picked up my carryon from baggage claim one of the wheels had broken off.

The flight changed gates multiple times and flight had to be delayed multiple times

We called Kayak for a change due to the TSA situation in Atlanta. What we got was a canceled return flight (in error) and we had to find the mistake. Not happy with Kayak who blamed it on AA.

Tv screens and movie selection v good. Friendly staff. They were really worried about max capacity and room for carryons. That is never fun but i had no problem finding space when I boarded.

I was in last row so that is never great bc the person in front of me leaned his seat all the way back into me.

Delayed for mechanical and no updates on what was happening and how long the delay might be.

My flight from LGA was cancelled and my rebooked flight from JFK was delayed numerous times. I will now be getting home after 2am.

Flight was delayed half hour before boarding, but when I checked flight aware the plane that would Pick us up had a delay of more than an hour. AA should let us know in advance to avoid waiting several hours in the airport

On the return flight, arriving in Denver we sat on the tarmac in Denver for over 20 minutes.

Typical AA - late by 90+ mn. Gate changed twice... Changed the departure time 6 times No explanation, no communication on reasons for delay I travel with AA twice a year... and it is consistently very poor.. I will continue to use AA only when i have to.

We had to take a bus to the plane with a old woman and carry on bags, and at landing at the airport we have to wait one hour seating on the plane waiting for a gate. We came back from Australia Bussines class Quantas 16 hours traveling, then wait in Dallas 7 hours for connection...honestly waiting 1 hour more at the plane was the worst part.

Flight delayed twice (not Spirit fault) No food served* No entertainment * *in response to my choices in the rating. None was provided so couldn’t rate properly

Delayed over two hours. Only knew about a 30 minute delay in advance

Poor service but I guess that’s what you get for picking cheap flight. Overacted with all extra up-charge fees, so annoying.

They canceled both the flight to Myrtle beach and the return flight. They are an awful airline and they ruined my trip. I will never book with Spirit again.

The flight was a big joke very uncomfortable I had a horrible experience and I will never fly with them again everything about the flight was bogus and I’m not happy with it at all this experience makes me not want to fly ever again

Pricing, boarding time communication, over priced baggage and overall service is lacking, seating unconfortable

Flight attendant was all so sweet and pilot got us to our destination safely and on time

They cancelled our flight. 2 hours before we were supposed to take off and offered us nothing! We got our money back and that was it. No other flight to get to our cruise no working with another airline or with us to get there. Terrible customer service, no apology.

we boarded the plane and then sat for OVER AN HOUR on it, first waiting for fuel and then the crew timed out. the flight kept getting delayed longer and longer, a 9:30pm flight is still on the ground at 1:15am.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports