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Caribbean Islands

$96+ Cheap flights from Indiana to Caribbean Islands

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/15. Fares are subject to change and may not be available on all flights or dates of travel.
IND — SJU
Aug 9 — Aug 161
Sat 8/9
Sat 8/16
1 adult, Economy
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Cheap flight deals from Indiana to Caribbean Islands

Keep the following information in mind while searching for Indiana to Caribbean Islands flight deals. Data was last updated August 4, 2025.

Round-trip from

$189
(FlightHub)

One-way from

$96
(Cheapflightsfares)

Popular in

December

Cheapest in

September

Average price

$413
From Indiana to Caribbean Islands
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One-way flight from Indiana to Caribbean Islands
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Highest demand for flights based on searches. 8% potential increase in price ($35 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($11 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Find flight deals from Indiana to Caribbean Islands

Cheapest flights from Indiana to Caribbean Islands
Explore the most affordable flight options available from Indiana to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 4, 2025.

This FlightHub deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/2711:36 amORD - STT
2 stops25h 12mSpirit Airlines
Wed 9/32:43 pmSTT - ORD
2 stops10h 16mSpirit Airlines
Deal found 8/3$189
This American Airlines deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/2611:00 amIND - SJU
2 stops12h 37mAmerican Airlines
Mon 9/2912:01 pmSJU - IND
1 stop11h 18mAmerican Airlines
Deal found 8/2$215
This Cheapflightsfares deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/166:56 amORD - SJU
1 stop16h 01mSpirit Airlines
Wed 8/201:39 pmSJU - ORD
Nonstop5h 11mSpirit Airlines
Deal found 8/3$224
This eDestinos deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/611:10 amIND - SJU
1 stop9h 46mSpirit Airlines
Sat 9/133:19 pmSJU - IND
1 stop7h 52mSpirit Airlines
Deal found 8/3$227
This eDestinos deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/26:56 amORD - SJU
1 stop16h 01mMultiple Airlines
Fri 9/53:39 amSJU - ORD
1 stop12h 38mMultiple Airlines
Deal found 8/1$232
This Cheapflightsfares deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/66:15 amMDW - SJU
1 stop6h 56mFrontier
Fri 9/123:39 amSJU - MDW
1 stop7h 12mFrontier
Deal found 8/3$236
This Frontier deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/67:49 pmORD - SJU
1 stop12h 06mFrontier
Tue 12/163:59 pmSJU - ORD
1 stop9h 12mFrontier
Deal found 8/2$238
This Frontier deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/28:00 amCVG - SJU
1 stop11h 08mFrontier
Fri 9/53:39 amSJU - CVG
1 stop9h 58mFrontier
Deal found 8/2$238
This American Airlines deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/101:05 pmCVG - SJU
1 stop10h 54mAmerican Airlines
Sat 10/185:30 amSJU - CVG
2 stops11h 29mAmerican Airlines
Deal found 8/2$240
This Delta deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/66:00 amIND - SJU
1 stop5h 40mDelta
Sat 9/137:00 amSJU - IND
1 stop9h 28mDelta
Deal found 8/4$245
This Frontier deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/66:26 pmIND - SJU
1 stop8h 08mFrontier
Thu 9/119:07 amSJU - IND
1 stop8h 51mFrontier
Deal found 8/3$248
This Gotogate deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/186:43 pmIND - SJU
1 stop7h 51mMultiple Airlines
Tue 10/212:48 amSJU - IND
1 stop6h 30mMultiple Airlines
Deal found 8/2$271

Cheapflights Fare Finder

 
Customize your flight search to find flights from Indiana to Caribbean Islands that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 4, 2025.
Use the filters below to find and compare flights from Indiana to Caribbean Islands that are best for you.

Fly from

Indiana

Fly to

Caribbean Islands

Route

Depart

Return

Price

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Wed 8/27

11:36 am-1:48 pm

2 stops25h 12m

Saint Thomas Island Cyril E King

Wed 9/3

2:43 pm-11:59 pm

2 stops10h 16m

$189

IndianapolisSan Juan

IND - SJU

INDSJU

Indianapolis

Fri 9/26

11:00 am-11:37 pm

2 stops12h 37m

San Juan Luis Munoz Marin Intl

Mon 9/29

12:01 pm-11:19 pm

1 stop11h 18m

$215

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 8/16

6:56 am-11:57 pm

1 stop16h 01m

San Juan Luis Munoz Marin Intl

Wed 8/20

1:39 pm-5:50 pm

Nonstop5h 11m

$224

IndianapolisSan Juan

IND - SJU

INDSJU

Indianapolis

Sat 9/6

11:10 am-8:56 pm

1 stop9h 46m

San Juan Luis Munoz Marin Intl

Sat 9/13

3:19 pm-11:11 pm

1 stop7h 52m

$227

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 9/2

6:56 am-11:57 pm

1 stop16h 01m

San Juan Luis Munoz Marin Intl

Fri 9/5

3:39 am-3:17 pm

1 stop12h 38m

$232

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sat 9/6

6:15 am-2:11 pm

1 stop6h 56m

San Juan Luis Munoz Marin Intl

Fri 9/12

3:39 am-9:51 am

1 stop7h 12m

$236

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 8/30

7:46 pm-8:59 am

1 stop12h 13m

San Juan Luis Munoz Marin Intl

Fri 9/5

3:39 am-3:17 pm

1 stop12h 38m

$238

CincinnatiSan Juan

CVG - SJU

CVGSJU

Cincinnati Cinci./N. Kentucky

Tue 9/2

8:00 am-7:08 pm

1 stop11h 08m

San Juan Luis Munoz Marin Intl

Fri 9/5

3:39 am-1:37 pm

1 stop9h 58m

$238

CincinnatiSan Juan

CVG - SJU

CVGSJU

Cincinnati Cinci./N. Kentucky

Fri 10/10

1:05 pm-11:59 pm

1 stop10h 54m

San Juan Luis Munoz Marin Intl

Sat 10/18

5:30 am-4:59 pm

2 stops11h 29m

$240

CincinnatiSan Juan

CVG - SJU

CVGSJU

Cincinnati Cinci./N. Kentucky

Sun 11/2

7:00 am-5:25 pm

1 stop9h 25m

San Juan Luis Munoz Marin Intl

Thu 11/6

2:26 pm-8:36 pm

1 stop7h 10m

$242

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/2

Showing 1-10 of 60 results
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Best time to book a flight from Indiana to Caribbean Islands

Have a flexible travel schedule? Discover the best time to fly to Caribbean Islands from Indiana with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Indiana to Caribbean Islands

What is the cheapest month to book a flight from Indiana to Caribbean Islands?

Currently, September is the cheapest month in which you can book a flight from Indiana to Caribbean Islands (average of $254). Flying from Indiana to Caribbean Islands in June is currently the most expensive (average of $339). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from IN to EPX?

Find hourly flight availability from Indiana to Caribbean Islands. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 4, 2025.

When flying from Indiana to Caribbean Islands, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Reviews of airlines servicing Caribbean Islands

Get insights into the airlines that provide service to Caribbean Islands. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Caribbean Islands. Reviews last updated August 4, 2025.
Read through reviews of airlines operating flights from Indiana to Caribbean Islands, such as Delta, Southwest, and Copa Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,987 reviews

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Food

7.3

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,987 reviews
Delta
8.0
Very good
7,987 reviews

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Food

7.3

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Southwest
8.0
Very good
4,246 reviews
Delta
8.0
Very good
7,987 reviews

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Food

7.3

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Copa Airlines
7.5
Good
1,500 reviews
Delta
8.0
Very good
7,987 reviews

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Food

7.3

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
United Airlines
7.4
Good
8,912 reviews
Delta
8.0
Very good
7,987 reviews

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Food

7.3

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,987 reviews

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Food

7.3

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

Related info for your journey

Find useful and relevant information for your journey from Indiana to Caribbean Islands. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What are the cheapest airlines to fly from Indiana to Caribbean Islands one-way?

    One-way options have recently been found by users for as low as $96 on Arajet. Other airlines that offer cheap prices include Spirit Airlines from $98 and Delta from $103 one-way.

  • Can I find deals for flights from Indiana to Caribbean Islands that include hotel bookings?

    Yes. In addition to deals on Indiana to Caribbean Islands flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Indiana to Caribbean Islands?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Indiana to Caribbean Islands.

  • Can I find deals for business class flights from Indiana to Caribbean Islands?

    Yes. Cheapflights offers flight deals from Indiana to Caribbean Islands by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Indiana to Caribbean Islands?

    Currently, September is the cheapest month in which you can book a flight from Indiana to Caribbean Islands (average of $254). Flying from Indiana to Caribbean Islands in June is currently the most expensive (average of $339). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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Alternative routes for Indiana to Caribbean Islands

See prices for flight routes from nearby airports that may be better suited for you.
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Top 6 airlines flying from Indiana to Caribbean Islands

Discover the top 6 airlines that operate flights from Indiana to Caribbean Islands. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 4, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$130Average$363FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$215Average$623FlexibilityNo cancel feeOn-time69%
Spirit AirlinesCheapest$224Average$376FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$225Average$758FlexibilityNo cancel feeOn-time63%
DeltaCheapest$253Average$622FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$264Average$666FlexibilityNo cancel feeOn-time71%

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