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Caribbean

$81+ 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 2/25. Fares are subject to change and may not be available on all flights or dates of travel.
IND — SJU
feb. 28 — mar. 71
sáb. 2/28
sáb. 3/7
1 adult, Economy
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Cheap 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 enero 29, 2026.

This Cheapflightsfares deal was found by Cheapflights users on 1/27. 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.
mar. 2/310:48 am
ORD
-
SJU
1 stop10h 45m
Spirit Airlines
mar. 2/101:22 pm
SJU
-
ORD
Nonstop5h 15m
Spirit Airlines
Deal found 1/27$185
This Priceline deal was found by Cheapflights users on 1/27. 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.
mar. 3/312:17 pm
ORD
-
SJU
Nonstop4h 32m
Spirit Airlines
sáb. 3/712:32 pm
SJU
-
ORD
Nonstop5h 16m
Spirit Airlines
Deal found 1/27$186
This Kiwi.com deal was found by Cheapflights users on 1/27. 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.
mar. 2/247:00 am
ORD
-
SJU
1 stop6h 31m
Spirit Airlines
mié. 3/1111:32 am
SJU
-
ORD
Nonstop5h 16m
Spirit Airlines
Deal found 1/27$187
This Kiwi.com deal was found by Cheapflights users on 1/28. 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.
mar. 2/247:00 am
ORD
-
SJU
1 stop6h 31m
Multiple Airlines
vie. 3/66:50 pm
SJU
-
ORD
1 stop17h 03m
Multiple Airlines
Deal found 1/28$188
This Kiwi.com deal was found by Cheapflights users on 1/28. 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.
mar. 2/247:00 am
ORD
-
SJU
1 stop6h 31m
Spirit Airlines
jue. 2/2612:32 pm
SJU
-
ORD
Nonstop5h 16m
Spirit Airlines
Deal found 1/28$189
This Kiwi.com deal was found by Cheapflights users on 1/27. 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.
lun. 2/233:50 pm
ORD
-
SJU
1 stop6h 53m
Multiple Airlines
lun. 3/911:32 am
SJU
-
ORD
Nonstop5h 16m
Multiple Airlines
Deal found 1/27$190
This JetBlue deal was found by Cheapflights users on 1/27. 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.
lun. 2/2310:00 am
ORD
-
SJU
1 stop10h 53m
JetBlue
mar. 2/245:10 am
SJU
-
ORD
1 stop8h 49m
JetBlue
Deal found 1/27$191
This Kiwi.com deal was found by Cheapflights users on 1/28. 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.
lun. 4/205:01 am
ORD
-
SJU
1 stop8h 07m
Multiple Airlines
sáb. 4/2512:22 pm
SJU
-
ORD
Nonstop5h 15m
Multiple Airlines
Deal found 1/28$192
This Mytrip deal was found by Cheapflights users on 1/29. 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.
mié. 3/1810:55 am
ORD
-
SJU
1 stop12h 03m
Spirit Airlines
mar. 3/2411:13 am
SJU
-
ORD
Nonstop5h 27m
Spirit Airlines
Deal found 1/29$193
This CheapOair deal was found by Cheapflights users on 1/28. 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.
mar. 2/2412:50 pm
ORD
-
SJU
1 stop7h 41m
Multiple Airlines
mié. 3/45:45 pm
SJU
-
ORD
1 stop8h 55m
Multiple Airlines
Deal found 1/28$194
This Expedia deal was found by Cheapflights users on 1/27. 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.
mar. 4/147:26 pm
ORD
-
SJU
Nonstop4h 33m
Multiple Airlines
mar. 4/2111:59 pm
SJU
-
ORD
1 stop8h 42m
Multiple Airlines
Deal found 1/27$195
This CheapOair deal was found by Cheapflights users on 1/27. 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.
sáb. 4/114:21 pm
ORD
-
SJU
1 stop14h 35m
Multiple Airlines
jue. 4/1612:22 pm
SJU
-
ORD
Nonstop5h 15m
Multiple Airlines
Deal found 1/27$196

Find flight deals from Indiana to Caribbean

Keep the following information in mind while searching for Indiana to Caribbean flight deals. Data was last updated enero 29, 2026.

Round-trip from

$185
(Expedia)

One-way from

$81
(Cheapflightsfares)

Popular in

December

Cheapest in

September

Average price

$395

Good one-way deal

$275 or less
From Indiana to Caribbean
Search Deals
One-way flight from Indiana to Caribbean
Search Deals
Highest demand for flights based on searches. 17% potential increase in price ($87 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease ($25 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals
Price to beat on a one-way 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 enero 29, 2026.
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

lun. 5/11

3:15 pm-2:07 am

1 stop9h 52m

San Juan Luis Munoz Marin Intl

mié. 5/13

11:59 pm-9:48 am

1 stop10h 49m

$191

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

sáb. 5/9

3:15 pm-2:07 am

1 stop9h 52m

San Juan Luis Munoz Marin Intl

vie. 5/15

11:59 pm-9:48 am

1 stop10h 49m

$192

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

lun. 3/9

12:41 pm-11:29 pm

1 stop9h 48m

San Juan Luis Munoz Marin Intl

lun. 3/16

3:26 am-11:25 am

1 stop8h 59m

$192

CincinnatiSan Juan

CVG - SJU

CVGSJU

Cincinnati Cinci./N. Kentucky

lun. 2/23

7:14 pm-2:53 am

1 stop6h 39m

San Juan Luis Munoz Marin Intl

mié. 2/25

3:53 am-11:12 am

1 stop8h 19m

$212

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

sáb. 2/21

6:04 am-4:56 pm

1 stop8h 52m

San Juan Luis Munoz Marin Intl

sáb. 2/28

5:10 am-12:04 pm

1 stop8h 54m

$215

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

vie. 4/10

10:00 am-10:01 pm

1 stop11h 01m

San Juan Luis Munoz Marin Intl

vie. 4/17

11:59 pm-7:41 am

1 stop8h 42m

$215

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

jue. 4/9

10:00 am-10:01 pm

1 stop11h 01m

San Juan Luis Munoz Marin Intl

vie. 4/17

11:59 pm-7:41 am

1 stop8h 42m

$215

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

jue. 3/12

12:20 pm-8:26 pm

1 stop7h 06m

San Juan Luis Munoz Marin Intl

lun. 3/23

3:26 am-11:25 am

1 stop8h 59m

$221

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

mar. 5/19

2:38 pm-8:34 pm

Nonstop4h 56m

San Juan Luis Munoz Marin Intl

vie. 5/29

7:40 am-11:53 am

Nonstop5h 13m

$237

CincinnatiSan Juan

CVG - SJU

CVGSJU

Cincinnati Cinci./N. Kentucky

mié. 2/25

4:15 pm-11:58 pm

1 stop6h 43m

San Juan Luis Munoz Marin Intl

mié. 3/4

7:30 am-5:01 pm

1 stop10h 31m

$246

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/27

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 December is currently the most expensive (average of $259). 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 enero 29, 2026.

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.

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?

    JetBlue, Frontier, and Delta can get you from Indiana to Caribbean in just under 6h 39m. Your travel time can differ by up to 3h 13m. There are 1809 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?

    $65 is the cheapest one-way deal found within the past few days, from Frontier. You may also be able to find cheap deals on Spirit Airlines and Southwest, with prices starting from $93 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 $143). Flying from Indiana to Caribbean in December is currently the most expensive (average of $259). 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

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 enero 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$130Average$363FlexibilityNo cancel feeOn-time62%
DeltaCheapest$150Average$629FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$191Average$416FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$215Average$764FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$215Average$599FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$251Average$667FlexibilityNo cancel feeOn-time71%

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