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Caribbean

$98+ Cheap flights from Indiana to Caribbean

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 8/30. Fares are subject to change and may not be available on all flights or dates of travel.
IND — SJU
Aug 5 — Aug 121
Tue 8/5
Tue 8/12
1 adult, Economy
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Cheap flight deals from Indiana to Caribbean

Keep the following information in mind while searching for Indiana to Caribbean flight deals. Data was last updated July 31, 2025.

Round-trip from

$215
(American Airlines)

One-way from

$96
(Cheapflightsfares)

Popular in

December

Cheapest in

September

Average price

$405
From Indiana to Caribbean
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One-way flight from Indiana to Caribbean
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Highest demand for flights based on searches. 8% potential increase in price ($34 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($12 potential savings vs. average RT price).
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Average for round-trip flights in July 2025
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Find flight deals from Indiana to Caribbean

Cheapest flights from Indiana to Caribbean
Explore the most affordable flight options available from Indiana to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 31, 2025.

This Delta deal was found by Cheapflights users on 7/29. 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.
Fri 10/246:00 amIND - SJU
1 stop10h 33mDelta
Tue 10/281:10 pmSJU - IND
1 stop7h 47mDelta
Deal found 7/29$215
This FlightHub deal was found by Cheapflights users on 7/31. 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.
Sat 8/3011:36 amORD - STT
2 stops25h 12mSpirit Airlines
Sat 9/610:49 amSTT - ORD
1 stop7h 50mSpirit Airlines
Deal found 7/31$216
This Booking.com deal was found by Cheapflights users on 7/30. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/106:23 pmORD - SJU
Nonstop4h 43mSpirit Airlines
Thu 8/147:40 pmSJU - ORD
Nonstop5h 03mSpirit Airlines
Deal found 7/30$224
This CheapOair deal was found by Cheapflights users on 7/29. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/66:24 pmIND - SJU
1 stop16h 40mSpirit Airlines
Fri 9/121:59 amSJU - IND
1 stop7h 19mSpirit Airlines
Deal found 7/29$227
This CheapOair deal was found by Cheapflights users on 7/29. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/308:47 pmORD - SJU
1 stop17h 20mMultiple Airlines
Fri 9/53:39 amSJU - ORD
1 stop12h 38mMultiple Airlines
Deal found 7/29$227
This United Airlines deal was found by Cheapflights users on 7/31. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/237:00 amIND - SJU
1 stop8h 42mUnited Airlines
Sat 9/271:05 amSJU - IND
1 stop8h 07mUnited Airlines
Deal found 7/31$232
This CheapOair deal was found by Cheapflights users on 7/29. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/611:10 amIND - SJU
2 stops23h 54mMultiple Airlines
Fri 9/123:39 amSJU - IND
1 stop13h 47mMultiple Airlines
Deal found 7/29$233
This Cheapflightsfares deal was found by Cheapflights users on 7/29. 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 8/3010:51 amMDW - SJU
1 stop7h 27mFrontier
Fri 9/53:39 amSJU - MDW
1 stop7h 12mFrontier
Deal found 7/29$235
This Priceline deal was found by Cheapflights users on 7/30. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/276:26 pmIND - SJU
1 stop8h 08mFrontier
Fri 10/33:39 amSJU - IND
1 stop13h 47mFrontier
Deal found 7/30$239
This American Airlines deal was found by Cheapflights users on 7/29. 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.
Wed 10/81:07 pmIND - SJU
1 stop9h 03mAmerican Airlines
Sun 10/125:30 amSJU - IND
1 stop9h 48mAmerican Airlines
Deal found 7/29$240
This Frontier deal was found by Cheapflights users on 7/30. 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 8/99:08 amORD - SJU
1 stop10h 21mFrontier
Wed 8/133:29 amSJU - ORD
1 stop12h 58mFrontier
Deal found 7/30$258
This FlightHub deal was found by Cheapflights users on 7/29. 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.
Sat 10/45:05 amORD - PUJ
1 stop8h 09mSpirit Airlines
Tue 10/73:19 pmPUJ - ORD
1 stop8h 29mSpirit Airlines
Deal found 7/29$298

Cheapflights Fare Finder

 
Customize your flight search to find flights from Indiana to Caribbean 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 July 31, 2025.
Use the filters below to find and compare flights from Indiana to Caribbean that are best for you.

Fly from

Indiana

Fly to

Caribbean

Route

Depart

Return

Price

IndianapolisSan Juan

IND - SJU

INDSJU

Indianapolis

Fri 10/24

6:00 am-4:33 pm

1 stop10h 33m

San Juan Luis Munoz Marin Intl

Tue 10/28

1:10 pm-8:57 pm

1 stop7h 47m

$215

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Sat 8/30

11:36 am-1:48 pm

2 stops25h 12m

Saint Thomas Island Cyril E King

Sat 9/6

10:49 am-5:39 pm

1 stop7h 50m

$216

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sun 8/10

6:23 pm-12:06 am

Nonstop4h 43m

San Juan Luis Munoz Marin Intl

Thu 8/14

7:40 pm-11:43 pm

Nonstop5h 03m

$224

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 8/30

8:47 pm-3:07 pm

1 stop17h 20m

San Juan Luis Munoz Marin Intl

Fri 9/5

3:39 am-3:17 pm

1 stop12h 38m

$227

IndianapolisSan Juan

IND - SJU

INDSJU

Indianapolis

Sat 9/6

6:24 pm-11:04 am

1 stop16h 40m

San Juan Luis Munoz Marin Intl

Fri 9/12

1:59 am-9:18 am

1 stop7h 19m

$227

IndianapolisSan Juan

IND - SJU

INDSJU

Indianapolis

Tue 9/23

7:00 am-3:42 pm

1 stop8h 42m

San Juan Luis Munoz Marin Intl

Sat 9/27

1:05 am-9:12 am

1 stop8h 07m

$232

IndianapolisSan Juan

IND - SJU

INDSJU

Indianapolis

Sat 9/6

11:10 am-11:04 am

2 stops23h 54m

San Juan Luis Munoz Marin Intl

Fri 9/12

3:39 am-5:26 pm

1 stop13h 47m

$233

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sat 8/30

10:51 am-7:18 pm

1 stop7h 27m

San Juan Luis Munoz Marin Intl

Fri 9/5

3:39 am-9:51 am

1 stop7h 12m

$235

IndianapolisSan Juan

IND - SJU

INDSJU

Indianapolis

Sat 9/27

6:26 pm-2:34 am

1 stop8h 08m

San Juan Luis Munoz Marin Intl

Fri 10/3

3:39 am-5:26 pm

1 stop13h 47m

$239

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 8/16

9:08 am-8:29 pm

1 stop10h 21m

San Juan Luis Munoz Marin Intl

Wed 8/20

8:13 pm-6:41 pm

1 stop23h 28m

$239

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/31

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

Have a flexible travel schedule? Discover the best time to fly to Caribbean 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

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

Currently, September is the cheapest month in which you can book a flight from Indiana to Caribbean (average of $254). Flying from Indiana to Caribbean 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 CB?

Find hourly flight availability from Indiana to Caribbean. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 31, 2025.

When flying from Indiana to Caribbean, 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

Get insights into the airlines that provide service to Caribbean. 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. Reviews last updated July 31, 2025.
Read reviews from past customers who have flown Delta, Southwest, and Copa Airlines from Indiana to Caribbean. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,981 reviews

Overall

8.0

Comfort

7.9

Crew

8.5

Boarding

8.2

Food

7.3

Entertainment

7.9

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
7,981 reviews
Delta
8.0
Very good
7,981 reviews

Overall

8.0

Comfort

7.9

Crew

8.5

Boarding

8.2

Food

7.3

Entertainment

7.9

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
7,981 reviews

Overall

8.0

Comfort

7.9

Crew

8.5

Boarding

8.2

Food

7.3

Entertainment

7.9

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
1,493 reviews
Delta
8.0
Very good
7,981 reviews

Overall

8.0

Comfort

7.9

Crew

8.5

Boarding

8.2

Food

7.3

Entertainment

7.9

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
8,900 reviews
Delta
8.0
Very good
7,981 reviews

Overall

8.0

Comfort

7.9

Crew

8.5

Boarding

8.2

Food

7.3

Entertainment

7.9

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
7,981 reviews

Overall

8.0

Comfort

7.9

Crew

8.5

Boarding

8.2

Food

7.3

Entertainment

7.9

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. 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 one-way?

    $96 is the cheapest one-way deal found within the past few days, from Arajet. You may also be able to find cheap deals on Spirit Airlines and American Airlines, with prices starting from $98 and $108, respectively.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Indiana to Caribbean 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?

    Currently, September is the cheapest month in which you can book a flight from Indiana to Caribbean (average of $254). Flying from Indiana to Caribbean 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

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Indiana to Caribbean

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

Discover the top 6 airlines that operate flights from Indiana to Caribbean. 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 July 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$130Average$363FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$215Average$624FlexibilityNo cancel feeOn-time69%
Spirit AirlinesCheapest$222Average$377FlexibilityNo cancel feeOn-time65%
DeltaCheapest$254Average$622FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$260Average$759FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$264Average$667FlexibilityNo cancel feeOn-time71%

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