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Caribbean Islands

$69+ 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 1/13. Fares are subject to change and may not be available on all flights or dates of travel.
IND — SJU
Dec 12 — Dec 191
Fri 12/12
Fri 12/19
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 November 12, 2025.

Round-trip from

$213
(Kiwi.com)

One-way from

$69
(Priceline)

Popular in

December

Cheapest in

September

Average price

$385
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. 14% potential increase in price ($68 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($20 potential savings vs. average RT price).
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Average for round-trip flights in November 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 November 12, 2025.

This Kiwi.com deal was found by Cheapflights users on 11/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/276:23 pmORD - SJU
2 stops24h 04mMultiple Airlines
Fri 12/53:06 pmSJU - ORD
1 stop7h 36mMultiple Airlines
Deal found 11/11$214
This Cheapflightsfares deal was found by Cheapflights users on 11/12. 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.
Fri 12/57:10 amORD - SJU
1 stop15h 35mSpirit Airlines
Wed 12/107:31 pmSJU - ORD
Nonstop5h 22mSpirit Airlines
Deal found 11/12$216
This Frontier deal was found by Cheapflights users on 11/11. 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.
Sun 12/76:37 pmMDW - SJU
1 stop13h 18mFrontier
Sat 12/204:02 pmSJU - MDW
1 stop8h 10mFrontier
Deal found 11/11$216
This Kiwi.com deal was found by Cheapflights users on 11/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/95:40 amORD - SJU
Nonstop4h 42mSpirit Airlines
Mon 12/158:45 pmSJU - ORD
Nonstop5h 14mSpirit Airlines
Deal found 11/11$217
This CheapOair deal was found by Cheapflights users on 11/11. 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 12/65:40 amORD - SJU
Nonstop4h 41mSpirit Airlines
Sun 12/148:45 pmSJU - ORD
Nonstop5h 14mSpirit Airlines
Deal found 11/11$218
This Kiwi.com deal was found by Cheapflights users on 11/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/226:00 amORD - SJU
1 stop17h 06mFrontier
Wed 11/266:01 amSJU - ORD
1 stop20h 07mFrontier
Deal found 11/12$219
This Kiwi.com deal was found by Cheapflights users on 11/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/31:03 pmORD - SJU
2 stops21h 29mMultiple Airlines
Sat 12/64:31 pmSJU - ORD
1 stop7h 53mMultiple Airlines
Deal found 11/9$220
This Kiwi.com deal was found by Cheapflights users on 11/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/47:23 pmMDW - SJU
2 stops27h 22mMultiple Airlines
Thu 12/1110:42 amSJU - MDW
1 stop13h 11mMultiple Airlines
Deal found 11/12$220
This Kiwi.com deal was found by Cheapflights users on 11/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/44:38 pmORD - SJU
1 stop23h 45mMultiple Airlines
Thu 12/114:31 pmSJU - ORD
1 stop7h 53mMultiple Airlines
Deal found 11/10$221
This Kiwi.com deal was found by Cheapflights users on 11/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/77:44 amMDW - SJU
1 stop30h 29mFrontier
Sat 12/131:59 amSJU - MDW
2 stops35h 09mFrontier
Deal found 11/9$221
This Cheapflightsfares deal was found by Cheapflights users on 11/10. 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.
Thu 11/2710:12 amORD - SJU
1 stop8h 15mSpirit Airlines
Fri 12/58:45 pmSJU - ORD
Nonstop5h 14mSpirit Airlines
Deal found 11/10$222
This Priceline deal was found by Cheapflights users on 11/11. 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 12/75:40 amORD - SJU
Nonstop4h 41mMultiple Airlines
Sat 12/133:55 amSJU - ORD
1 stop11h 36mMultiple Airlines
Deal found 11/11$223

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 November 12, 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

Mon 2/2

2:20 pm-9:00 pm

Nonstop4h 40m

San Juan Luis Munoz Marin Intl

Fri 2/6

2:05 am-9:40 am

1 stop9h 35m

$223

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sun 2/1

2:20 pm-9:00 pm

Nonstop4h 40m

San Juan Luis Munoz Marin Intl

Tue 2/3

2:05 am-10:53 am

1 stop10h 48m

$223

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Fri 1/23

10:53 am-11:44 pm

1 stop10h 51m

San Juan Luis Munoz Marin Intl

Tue 1/27

3:55 pm-10:26 pm

1 stop8h 31m

$225

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Tue 2/3

8:25 am-5:05 pm

1 stop6h 40m

San Juan Luis Munoz Marin Intl

Tue 2/10

6:10 am-11:35 am

1 stop7h 25m

$227

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Wed 2/4

7:01 am-4:52 pm

1 stop7h 51m

San Juan Luis Munoz Marin Intl

Sat 2/14

6:15 am-1:39 pm

1 stop9h 24m

$227

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sun 2/1

1:00 pm-10:22 pm

1 stop7h 22m

San Juan Luis Munoz Marin Intl

Fri 2/6

2:05 am-9:40 am

1 stop9h 35m

$227

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Mon 2/2

6:00 am-2:30 pm

1 stop6h 30m

San Juan Luis Munoz Marin Intl

Wed 2/4

3:55 pm-10:26 pm

1 stop8h 31m

$227

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sat 1/24

12:15 pm-11:00 pm

1 stop8h 45m

San Juan Luis Munoz Marin Intl

Tue 1/27

9:05 am-6:35 pm

1 stop11h 30m

$245

CincinnatiSan Juan

CVG - SJU

CVGSJU

Cincinnati Cinci./N. Kentucky

Wed 11/26

9:25 pm-9:56 am

1 stop11h 31m

San Juan Luis Munoz Marin Intl

Sun 11/30

6:01 am-10:21 am

1 stop29h 20m

$246

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Mon 12/8

7:10 am-4:50 pm

1 stop7h 40m

Punta Cana

Mon 12/15

6:08 pm-12:09 am

1 stop8h 01m

$264

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/9

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 $143). Flying from Indiana to Caribbean Islands in July is currently the most expensive (average of $246). 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 November 12, 2025.

One of the essential ways to save on airfare from Indiana to Caribbean Islands is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight at noon could potentially save you up to 22% on airfare.

What is the cheapest day to fly from Indiana to Caribbean Islands?

Use this chart to determine the cheapest time to fly round-trip from Indiana to Caribbean Islands. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Indiana to Caribbean Islands flight should consider departing on Thursday at noon when fares are most often at their lowest. Tuesday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

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.

  • How long is the flight from Indiana to Caribbean Islands?

    United Airlines, Delta, and Southwest can get you from Indiana to Caribbean Islands in just under 4h 40m. Your travel time can differ by up to 6h 11m. Indiana and Caribbean Islands are separated by a distance of 2073 mi. This flight may include one or multiple stops.

  • 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 $69 on Frontier. Other airlines that offer cheap prices include Spirit Airlines from $109 and Delta 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 $143). Flying from Indiana to Caribbean Islands in July is currently the most expensive (average of $246). 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 November 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$130Average$372FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$215Average$785FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$215Average$601FlexibilityNo cancel feeOn-time69%
DeltaCheapest$215Average$617FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$229Average$379FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$265Average$642FlexibilityNo cancel feeOn-time71%

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