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$84+ 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 11/15. Fares are subject to change and may not be available on all flights or dates of travel.
IND — SJU
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
1 adult, Economy
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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 October 30, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/204:51 pmORD - SJU
1 stop21h 37mMultiple Airlines
Mon 11/245:19 pmSJU - ORD
1 stop28h 02mMultiple Airlines
Deal found 10/30$210
This Priceline deal was found by Cheapflights users on 10/30. 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.
Sun 12/76:00 amORD - SJU
1 stop12h 08mMultiple Airlines
Fri 12/124:10 amSJU - ORD
1 stop8h 58mMultiple Airlines
Deal found 10/30$211
This Cheapflightsfares deal was found by Cheapflights users on 10/30. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/165:10 amORD - SJU
1 stop10h 09mSpirit Airlines
Sat 11/224:12 pmSJU - ORD
Nonstop5h 11mSpirit Airlines
Deal found 10/30$212
This Mytrip deal was found by Cheapflights users on 10/30. 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.
Thu 11/278:41 amORD - SJU
Nonstop4h 36mMultiple Airlines
Thu 12/44:31 pmSJU - ORD
1 stop7h 53mMultiple Airlines
Deal found 10/30$213
This Priceline deal was found by Cheapflights users on 10/30. 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.
Fri 12/52:00 pmORD - SJU
1 stop18h 47mMultiple Airlines
Sun 12/78:45 pmSJU - ORD
Nonstop5h 14mMultiple Airlines
Deal found 10/30$214
This Frontier deal was found by Cheapflights users on 10/29. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/246:15 pmORD - SJU
1 stop6h 39mFrontier
Thu 11/274:05 pmSJU - ORD
1 stop10h 03mFrontier
Deal found 10/29$215
This Frontier deal was found by Cheapflights users on 10/30. 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.
Thu 12/117:40 amORD - SJU
1 stop10h 28mFrontier
Sat 12/204:02 pmSJU - ORD
1 stop8h 44mFrontier
Deal found 10/30$216
This Kiwi.com deal was found by Cheapflights users on 10/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/288:41 amORD - SJU
Nonstop4h 36mMultiple Airlines
Thu 12/410:42 amSJU - ORD
1 stop9h 54mMultiple Airlines
Deal found 10/30$217
This Priceline deal was found by Cheapflights users on 10/29. 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.
Thu 11/278:41 amORD - SJU
Nonstop4h 36mSpirit Airlines
Sat 12/67:31 pmSJU - ORD
Nonstop5h 22mSpirit Airlines
Deal found 10/29$218
This Mytrip deal was found by Cheapflights users on 10/29. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/76:00 amORD - SJU
1 stop12h 08mFrontier
Wed 12/104:31 pmSJU - ORD
1 stop26h 56mFrontier
Deal found 10/29$219
This Frontier deal was found by Cheapflights users on 10/29. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/148:26 amORD - SJU
2 stops15h 06mFrontier
Sat 11/227:11 amSJU - ORD
1 stop12h 48mFrontier
Deal found 10/29$220
This Frontier deal was found by Cheapflights users on 10/30. 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.
Sun 12/76:00 amORD - SJU
1 stop12h 08mFrontier
Fri 12/123:55 amSJU - ORD
2 stops20h 29mFrontier
Deal found 10/30$221

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 October 30, 2025.

Round-trip from

$209
(Frontier)

One-way from

$84
(Mytrip)

Popular in

December

Cheapest in

September

Average price

$407

Good round-trip deal

$543 or less
From Indiana to Caribbean
Search Deals
One-way flight from Indiana to Caribbean
Search Deals
Highest demand for flights based on searches. 9% potential increase in price ($38 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($12 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals
Price to beat on a round-trip flight from Indiana to Caribbean.
Search Deals

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 October 30, 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

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sun 2/8

2:20 pm-9:00 pm

Nonstop4h 40m

San Juan Luis Munoz Marin Intl

Fri 2/13

8:35 am-11:57 am

Nonstop5h 22m

$218

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mon 1/12

2:20 pm-9:00 pm

Nonstop4h 40m

San Juan Luis Munoz Marin Intl

Wed 2/4

2:05 am-10:53 am

1 stop10h 48m

$223

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Wed 1/21

2:20 pm-9:00 pm

Nonstop4h 40m

San Juan Luis Munoz Marin Intl

Wed 1/28

2:05 am-9:40 am

1 stop9h 35m

$223

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mon 1/19

2:49 pm-11:44 pm

1 stop6h 55m

San Juan Luis Munoz Marin Intl

Tue 2/3

7:00 am-5:45 pm

1 stop12h 45m

$227

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sun 1/18

5:33 am-5:17 pm

1 stop9h 44m

San Juan Luis Munoz Marin Intl

Fri 1/30

7:00 am-5:45 pm

1 stop12h 45m

$227

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Tue 1/20

10:53 am-11:44 pm

1 stop10h 51m

San Juan Luis Munoz Marin Intl

Wed 1/28

3:55 pm-10:26 pm

1 stop8h 31m

$227

CincinnatiSan Juan

CVG - SJU

CVGSJU

Cincinnati Cinci./N. Kentucky

Thu 11/13

8:00 am-11:52 pm

1 stop14h 52m

San Juan Luis Munoz Marin Intl

Sat 11/15

6:25 am-3:35 pm

1 stop10h 10m

$250

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mon 1/19

2:49 pm-11:44 pm

1 stop6h 55m

San Juan Luis Munoz Marin Intl

Sat 1/31

7:30 am-1:49 pm

1 stop8h 19m

$252

CincinnatiSan Juan

CVG - SJU

CVGSJU

Cincinnati Cinci./N. Kentucky

Sun 2/1

6:25 am-4:36 pm

1 stop9h 11m

San Juan Luis Munoz Marin Intl

Mon 2/9

2:05 am-10:45 am

1 stop9h 40m

$252

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 1/24

10:24 am-11:59 pm

1 stop11h 35m

San Juan Luis Munoz Marin Intl

Fri 1/30

7:00 am-5:45 pm

1 stop12h 45m

$252

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/30

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 $143). Flying from Indiana to Caribbean in July is currently the most expensive (average of $248). 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 October 30, 2025.

One of the essential ways to save on airfare from Indiana to Caribbean 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 18% on airfare.

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

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

Travelers seeking maximum savings on their Indiana to Caribbean 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. 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?

    United Airlines, Delta, and American Airlines can get you from Indiana to Caribbean in just under 4h 40m. Your travel time can differ by up to 10h 12m. There are 2073 mi between Indiana and Caribbean. This flight may include one or multiple stops.

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

    $84 is the cheapest one-way deal found within the past few days, from Frontier. You may also be able to find cheap deals on American Airlines and United Airlines, with prices starting from $113 and $113, 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 $143). Flying from Indiana to Caribbean in July is currently the most expensive (average of $248). 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

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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$130Average$372FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$215Average$785FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$215Average$596FlexibilityNo cancel feeOn-time69%
DeltaCheapest$215Average$635FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$229Average$377FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$264Average$667FlexibilityNo cancel feeOn-time71%

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