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Caribbean Islands

$77+ 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 2/28. Fares are subject to change and may not be available on all flights or dates of travel.
IND — SJU
Jan 30 — Feb 61
Fri 1/30
Fri 2/6
1 adult, Economy
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Cheap 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 December 31, 2025.

This Expedia deal was found by Cheapflights users on 12/30. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/316:45 amORD - SJU
1 stop7h 41mJetBlue
Thu 1/811:06 amSJU - ORD
1 stop10h 30mJetBlue
Deal found 12/30$243
This JetBlue deal was found by Cheapflights users on 12/29. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/316:45 amORD - SJU
1 stop7h 41mJetBlue
Thu 1/1511:06 amSJU - ORD
1 stop10h 30mJetBlue
Deal found 12/29$286
This Expedia deal was found by Cheapflights users on 12/30. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/316:45 amORD - SJU
1 stop7h 41mMultiple Airlines
Fri 1/97:10 amSJU - ORD
1 stop11h 57mMultiple Airlines
Deal found 12/30$288
This Mytrip deal was found by Cheapflights users on 12/30. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/317:10 amORD - PUJ
Nonstop4h 37mMultiple Airlines
Sun 1/113:35 pmPUJ - ORD
1 stop30h 35mMultiple Airlines
Deal found 12/30$299
This Priceline deal was found by Cheapflights users on 12/30. 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.
Wed 12/316:45 amORD - SJU
1 stop10h 04mMultiple Airlines
Fri 1/93:55 amSJU - ORD
1 stop17h 22mMultiple Airlines
Deal found 12/30$302
This CheapOair deal was found by Cheapflights users on 12/29. 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.
Wed 12/315:45 amORD - SJU
Nonstop4h 41mSpirit Airlines
Thu 1/151:22 pmSJU - ORD
Nonstop5h 15mSpirit Airlines
Deal found 12/29$319
This Priceline deal was found by Cheapflights users on 12/29. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/316:45 amORD - SJU
1 stop10h 04mMultiple Airlines
Thu 1/84:39 pmSJU - ORD
1 stop8h 00mMultiple Airlines
Deal found 12/29$325
This Kiwi.com deal was found by Cheapflights users on 12/31. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/316:05 pmORD - SJU
1 stop23h 08mMultiple Airlines
Tue 1/139:00 amSJU - ORD
1 stop9h 52mMultiple Airlines
Deal found 12/31$330
This JetBlue deal was found by Cheapflights users on 12/30. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/316:45 amORD - SJU
1 stop10h 04mJetBlue
Sat 1/108:00 amSJU - ORD
1 stop11h 43mJetBlue
Deal found 12/30$335
This Kiwi.com deal was found by Cheapflights users on 12/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/313:32 pmMDW - SJU
1 stop15h 07mFrontier
Sun 1/1110:47 pmSJU - MDW
1 stop17h 19mFrontier
Deal found 12/29$336
This Mytrip deal was found by Cheapflights users on 12/31. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/317:10 amORD - PUJ
Nonstop4h 37mMultiple Airlines
Wed 1/74:55 pmPUJ - ORD
1 stop27h 56mMultiple Airlines
Deal found 12/31$337
This Priceline deal was found by Cheapflights users on 12/29. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/316:45 amORD - SJU
1 stop10h 04mMultiple Airlines
Wed 1/79:19 pmSJU - ORD
1 stop20h 09mMultiple Airlines
Deal found 12/29$343

Find 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 December 31, 2025.

Round-trip from

$192
(CheapOair)

One-way from

$77
(Frontier)

Popular in

December

Cheapest in

September

Average price

$615
From Indiana to Caribbean Islands
Search Deals
One-way flight from Indiana to Caribbean Islands
Search Deals
Highest demand for flights based on searches. 15% potential increase in price ($73 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($21 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

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 December 31, 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 1/27

7:45 am-6:02 pm

1 stop8h 17m

San Juan Luis Munoz Marin Intl

Sun 2/1

9:25 am-6:32 pm

1 stop11h 07m

$196

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mon 3/2

12:41 pm-12:29 am

1 stop9h 48m

San Juan Luis Munoz Marin Intl

Mon 3/9

4:15 am-11:49 am

1 stop8h 34m

$196

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Fri 2/27

10:00 am-10:03 pm

1 stop10h 03m

San Juan Luis Munoz Marin Intl

Thu 3/5

1:44 pm-10:59 pm

1 stop11h 15m

$196

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Fri 2/27

10:00 am-10:03 pm

1 stop10h 03m

San Juan Luis Munoz Marin Intl

Sat 2/28

5:10 am-12:04 pm

1 stop8h 54m

$199

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Fri 1/9

7:45 am-6:07 pm

1 stop8h 22m

San Juan Luis Munoz Marin Intl

Thu 1/15

11:06 am-7:36 pm

1 stop10h 30m

$202

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Fri 2/27

12:41 pm-12:29 am

1 stop9h 48m

San Juan Luis Munoz Marin Intl

Sat 3/7

5:10 am-11:58 am

1 stop8h 48m

$202

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Fri 1/9

7:45 am-6:07 pm

1 stop8h 22m

San Juan Luis Munoz Marin Intl

Wed 1/14

11:06 am-7:36 pm

1 stop10h 30m

$202

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mon 3/2

8:55 am-3:40 pm

Nonstop4h 45m

San Juan Luis Munoz Marin Intl

Fri 3/6

8:30 am-11:52 am

Nonstop5h 22m

$216

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Tue 1/20

10:48 am-11:45 pm

1 stop10h 57m

San Juan Luis Munoz Marin Intl

Thu 1/22

7:30 am-11:59 am

1 stop6h 29m

$225

CincinnatiSan Juan

CVG - SJU

CVGSJU

Cincinnati Cinci./N. Kentucky

Sat 1/31

11:32 am-11:56 pm

1 stop11h 24m

San Juan Luis Munoz Marin Intl

Tue 2/10

6:00 am-3:37 pm

2 stops10h 37m

$225

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/31

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 December is currently the most expensive (average of $258). 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 December 31, 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.

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?

    JetBlue, Delta, and American Airlines can get you from Indiana to Caribbean Islands in just under 8h 17m. Your travel time can differ by up to 3h 07m. 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 $65 on Frontier. Other airlines that offer cheap prices include Spirit Airlines from $79 and Delta from $108 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 December is currently the most expensive (average of $258). 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 December 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$130Average$363FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$191Average$417FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$215Average$793FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$215Average$614FlexibilityNo cancel feeOn-time69%
DeltaCheapest$215Average$637FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$265Average$664FlexibilityNo cancel feeOn-time71%

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