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Caribbean Islands

$93+ 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 6/28. Fares are subject to change and may not be available on all flights or dates of travel.
IND — SJU
Jun 23 — Jun 301
Mon 6/23
Mon 6/30
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 June 18, 2025.

Round-trip from

$213
(Priceline)

One-way from

$93
(Priceline)

Popular in

December

Cheapest in

September

Average price

$433
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. 6% potential increase in price ($27 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 June 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 June 18, 2025.

This Priceline deal was found by Cheapflights users on 6/17. 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.
Tue 6/2411:28 amORD - SJU
1 stop14h 07mFrontier
Mon 6/305:40 amSJU - ORD
1 stop29h 37mFrontier
Deal found 6/17$212
This FlightHub deal was found by Cheapflights users on 6/17. 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.
Tue 7/810:43 amORD - SJU
1 stop12h 22mSpirit Airlines
Tue 7/154:43 pmSJU - ORD
1 stop15h 21mSpirit Airlines
Deal found 6/17$215
This Priceline deal was found by Cheapflights users on 6/15. 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.
Sun 6/2912:03 pmORD - SJU
Nonstop4h 44mMultiple Airlines
Fri 7/410:59 amSJU - ORD
1 stop9h 18mMultiple Airlines
Deal found 6/15$220
This Priceline deal was found by Cheapflights users on 6/14. 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.
Sun 6/299:12 pmMDW - SJU
1 stop28h 23mFrontier
Fri 7/43:34 amSJU - MDW
1 stop17h 48mFrontier
Deal found 6/14$221
This American Airlines deal was found by Cheapflights users on 6/16. 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.
Tue 9/166:49 pmCVG - SJU
2 stops17h 57mAmerican Airlines
Tue 9/236:10 amSJU - CVG
2 stops15h 52mAmerican Airlines
Deal found 6/16$250
This Cheapflightsfares deal was found by Cheapflights users on 6/16. 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.
Sun 7/137:27 pmCVG - SJU
1 stop7h 12mFrontier
Thu 7/175:15 pmSJU - CVG
1 stop6h 39mFrontier
Deal found 6/16$251
This Delta deal was found by Cheapflights users on 6/17. 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.
Sun 11/25:00 amCVG - SJU
1 stop5h 47mDelta
Tue 11/187:30 amSJU - CVG
1 stop9h 07mDelta
Deal found 6/17$252
This Booking.com deal was found by Cheapflights users on 6/17. 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.
Tue 7/87:49 pmORD - STT
1 stop15h 41mSpirit Airlines
Tue 7/224:05 pmSTT - ORD
1 stop8h 06mSpirit Airlines
Deal found 6/17$255
This Frontier deal was found by Cheapflights users on 6/17. 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.
Fri 8/155:51 pmIND - SJU
1 stop6h 55mFrontier
Wed 8/203:59 amSJU - IND
1 stop8h 14mFrontier
Deal found 6/17$258
This FlightHub deal was found by Cheapflights users on 6/15. 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.
Tue 7/811:24 amIND - SJU
1 stop12h 41mSpirit Airlines
Thu 7/102:40 amSJU - IND
2 stops12h 44mSpirit Airlines
Deal found 6/15$260
This Trip.com deal was found by Cheapflights users on 6/17. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/305:44 pmIND - SJU
1 stop6h 56mMultiple Airlines
Thu 7/312:59 amSJU - IND
2 stops15h 56mMultiple Airlines
Deal found 6/17$265
This United Airlines deal was found by Cheapflights users on 6/17. 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.
Fri 10/175:50 amIND - SJU
1 stop6h 44mUnited Airlines
Sat 10/257:00 amSJU - IND
1 stop8h 35mUnited Airlines
Deal found 6/17$270

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 June 18, 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

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 6/24

11:28 am-2:35 am

1 stop14h 07m

San Juan Luis Munoz Marin Intl

Mon 6/30

5:40 am-10:17 am

1 stop29h 37m

$212

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 7/8

10:43 am-12:05 am

1 stop12h 22m

San Juan Luis Munoz Marin Intl

Tue 7/15

4:43 pm-7:04 am

1 stop15h 21m

$215

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sun 6/29

12:03 pm-5:47 pm

Nonstop4h 44m

San Juan Luis Munoz Marin Intl

Fri 7/4

10:59 am-7:17 pm

1 stop9h 18m

$220

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sun 6/29

9:12 pm-2:35 am

1 stop28h 23m

San Juan Luis Munoz Marin Intl

Fri 7/4

3:34 am-8:22 pm

1 stop17h 48m

$221

CincinnatiSan Juan

CVG - SJU

CVGSJU

Cincinnati Cinci./N. Kentucky

Tue 9/16

6:49 pm-12:46 pm

2 stops17h 57m

San Juan Luis Munoz Marin Intl

Tue 9/23

6:10 am-10:02 pm

2 stops15h 52m

$250

CincinnatiSan Juan

CVG - SJU

CVGSJU

Cincinnati Cinci./N. Kentucky

Sun 7/13

7:27 pm-2:39 am

1 stop7h 12m

San Juan Luis Munoz Marin Intl

Thu 7/17

5:15 pm-11:54 pm

1 stop6h 39m

$251

CincinnatiSan Juan

CVG - SJU

CVGSJU

Cincinnati Cinci./N. Kentucky

Sun 11/2

5:00 am-11:47 am

1 stop5h 47m

San Juan Luis Munoz Marin Intl

Tue 11/18

7:30 am-3:37 pm

1 stop9h 07m

$252

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Tue 7/8

7:49 pm-12:30 pm

1 stop15h 41m

Saint Thomas Island Cyril E King

Tue 7/22

4:05 pm-11:11 pm

1 stop8h 06m

$255

IndianapolisSan Juan

IND - SJU

INDSJU

Indianapolis

Fri 8/15

5:51 pm-12:46 am

1 stop6h 55m

San Juan Luis Munoz Marin Intl

Wed 8/20

3:59 am-12:13 pm

1 stop8h 14m

$258

IndianapolisSan Juan

IND - SJU

INDSJU

Indianapolis

Tue 7/8

11:24 am-12:05 am

1 stop12h 41m

San Juan Luis Munoz Marin Intl

Thu 7/10

2:40 am-3:24 pm

2 stops12h 44m

$260

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/17

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 June 18, 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.

Rainfall in Caribbean Islands by month

Plan your trip to Caribbean Islands by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Caribbean Islands ranges from 2.2 - 6.1 inches per month. November is typically the wettest month, when rainfall can reach 6.1 in. February is typically the driest time to visit Caribbean Islands when rainfall is around 2.2 in.

Temperature in Caribbean Islands by month

Plan your trip to Caribbean Islands by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Caribbean Islands, use this chart to help with planning. For those seeking warmer temperatures, June is the ideal time of year to visit, when temperatures reach an average of 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 77.0 F).

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 June 18, 2025.
To help decide which airline to fly from Indiana to Caribbean Islands, see what other customers have to say about Delta, Southwest and Air Transat. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,964 reviews

Food

7.3

Overall

8.0

Boarding

8.2

Comfort

7.9

Crew

8.5

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
7,964 reviews
Delta
8.0
Very good
7,964 reviews

Food

7.3

Overall

8.0

Boarding

8.2

Comfort

7.9

Crew

8.5

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
4,278 reviews
Delta
8.0
Very good
7,964 reviews

Food

7.3

Overall

8.0

Boarding

8.2

Comfort

7.9

Crew

8.5

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!
Air Transat
7.8
Good
398 reviews
Delta
8.0
Very good
7,964 reviews

Food

7.3

Overall

8.0

Boarding

8.2

Comfort

7.9

Crew

8.5

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
1,455 reviews
Delta
8.0
Very good
7,964 reviews

Food

7.3

Overall

8.0

Boarding

8.2

Comfort

7.9

Crew

8.5

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
8,809 reviews
Delta
8.0
Very good
7,964 reviews

Food

7.3

Overall

8.0

Boarding

8.2

Comfort

7.9

Crew

8.5

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 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 $93 on Frontier. Other airlines that offer cheap prices include Arajet from $111 and Southwest from $113 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 June 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$130Average$343FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$204Average$386FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$215Average$627FlexibilityNo cancel feeOn-time69%
DeltaCheapest$254Average$628FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$265Average$652FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$338Average$762FlexibilityNo cancel feeOn-time63%

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