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$95+ 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 8/18. Fares are subject to change and may not be available on all flights or dates of travel.
IND — SJU
jun. 17 — jun. 241
mar. 6/17
mar. 6/24
1 adult, Economy
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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 junio 12, 2025.

Round-trip from

$210
(FlightHub)

One-way from

$95
(Priceline)

Popular in

December

Cheapest in

September

Average price

$434

Good round-trip deal

$450 or less
From Indiana to Caribbean
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One-way flight from Indiana to Caribbean
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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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Price to beat on a round-trip flight from Indiana to Caribbean.
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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 junio 12, 2025.

This FlightHub deal was found by Cheapflights users on 6/10. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 8/187:45 amORD - SJU
1 stop7h 58mFrontier
jue. 8/213:21 pmSJU - ORD
1 stop9h 33mFrontier
Deal found 6/10$210
This Priceline deal was found by Cheapflights users on 6/10. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 8/292:05 pmMDW - SJU
1 stop8h 49mFrontier
vie. 9/54:42 pmSJU - MDW
1 stop20h 14mFrontier
Deal found 6/10$212
This Cheapflightsfares deal was found by Cheapflights users on 6/11. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 7/810:43 amORD - SJU
1 stop12h 22mSpirit Airlines
mar. 7/154:43 pmSJU - ORD
1 stop15h 21mSpirit Airlines
Deal found 6/11$214
This Priceline deal was found by Cheapflights users on 6/11. 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.
sáb. 7/1212:20 pmORD - SJU
1 stop11h 07mMultiple Airlines
mar. 7/224:43 pmSJU - ORD
1 stop15h 21mMultiple Airlines
Deal found 6/11$220
This Frontier deal was found by Cheapflights users on 6/9. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 6/158:45 amCVG - SJU
1 stop7h 05mFrontier
jue. 6/192:05 pmSJU - CVG
1 stop9h 44mFrontier
Deal found 6/9$262
This American Airlines deal was found by Cheapflights users on 6/11. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 9/235:32 amCVG - SJU
2 stops9h 21mAmerican Airlines
mar. 9/306:10 amSJU - CVG
2 stops16h 54mAmerican Airlines
Deal found 6/11$265
This Cheapflightsfares deal was found by Cheapflights users on 6/10. 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.
mar. 7/87:49 pmORD - STT
1 stop15h 41mSpirit Airlines
mar. 7/151:25 pmSTT - ORD
1 stop10h 46mSpirit Airlines
Deal found 6/10$271
This Southwest deal was found by Cheapflights users on 6/10. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 7/42:00 pmCVG - SJU
1 stop7h 40mSouthwest
mar. 7/811:35 amSJU - CVG
1 stop11h 45mSouthwest
Deal found 6/10$274
This Mytrip deal was found by Cheapflights users on 6/10. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 7/27:30 amCVG - SJU
1 stop11h 49mMultiple Airlines
mié. 7/94:43 pmSJU - CVG
2 stops19h 27mMultiple Airlines
Deal found 6/10$279
This American Airlines deal was found by Cheapflights users on 6/10. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 7/18:35 amORD - PUJ
Nonstop4h 35mAmerican Airlines
vie. 7/43:31 pmPUJ - ORD
Nonstop5h 05mAmerican Airlines
Deal found 6/10$294
This JetBlue deal was found by Cheapflights users on 6/10. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 11/44:05 pmORD - SJU
1 stop7h 38mJetBlue
mar. 11/117:30 amSJU - ORD
1 stop9h 38mJetBlue
Deal found 6/10$297
This Vliegwinkel deal was found by Cheapflights users on 6/10. 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 Vliegwinkel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 7/148:45 pmORD - PUJ
1 stop13h 16mRoyal Air Maroc
mar. 7/224:10 pmPUJ - ORD
2 stops18h 25mRoyal Air Maroc
Deal found 6/10$303

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 junio 12, 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

lun. 8/18

7:45 am-4:43 pm

1 stop7h 58m

San Juan Luis Munoz Marin Intl

jue. 8/21

3:21 pm-11:54 pm

1 stop9h 33m

$210

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

vie. 8/29

2:05 pm-11:54 pm

1 stop8h 49m

San Juan Luis Munoz Marin Intl

vie. 9/5

4:42 pm-11:56 am

1 stop20h 14m

$212

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

mar. 7/8

10:43 am-12:05 am

1 stop12h 22m

San Juan Luis Munoz Marin Intl

mar. 7/15

4:43 pm-7:04 am

1 stop15h 21m

$214

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

sáb. 7/12

12:20 pm-12:27 am

1 stop11h 07m

San Juan Luis Munoz Marin Intl

mar. 7/22

4:43 pm-7:04 am

1 stop15h 21m

$220

CincinnatiSan Juan

CVG - SJU

CVGSJU

Cincinnati Cinci./N. Kentucky

dom. 6/15

8:45 am-3:50 pm

1 stop7h 05m

San Juan Luis Munoz Marin Intl

jue. 6/19

2:05 pm-11:49 pm

1 stop9h 44m

$262

CincinnatiSan Juan

CVG - SJU

CVGSJU

Cincinnati Cinci./N. Kentucky

mar. 8/26

6:00 am-6:15 pm

2 stops12h 15m

San Juan Luis Munoz Marin Intl

mié. 9/3

6:10 am-6:40 pm

1 stop12h 30m

$265

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

mar. 7/8

7:49 pm-12:30 pm

1 stop15h 41m

Saint Thomas Island Cyril E King

mar. 7/15

1:25 pm-11:11 pm

1 stop10h 46m

$271

CincinnatiSan Juan

CVG - SJU

CVGSJU

Cincinnati Cinci./N. Kentucky

vie. 7/4

2:00 pm-9:40 pm

1 stop7h 40m

San Juan Luis Munoz Marin Intl

mar. 7/8

11:35 am-11:20 pm

1 stop11h 45m

$274

CincinnatiSan Juan

CVG - SJU

CVGSJU

Cincinnati Cinci./N. Kentucky

mié. 7/2

7:30 am-7:19 pm

1 stop11h 49m

San Juan Luis Munoz Marin Intl

mié. 7/9

4:43 pm-12:10 pm

2 stops19h 27m

$279

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

mar. 7/1

8:35 am-2:10 pm

Nonstop4h 35m

Punta Cana

vie. 7/4

3:31 pm-7:36 pm

Nonstop5h 05m

$294

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/9

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 $254). Flying from Indiana to Caribbean 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 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 junio 12, 2025.

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.

Rainfall in Caribbean by month

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

In terms of precipitation, rainfall in Caribbean 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 when rainfall is around 2.2 in.

Temperature in Caribbean by month

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

If weather is an important factor for your trip to Caribbean, 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

Get insights into the airlines that provide service to Caribbean. 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. Reviews last updated junio 12, 2025.
Delta
8.0
Very good
7,946 reviews

Overall

8.0

Food

7.3

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Crew

8.5

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
7,946 reviews
Delta
8.0
Very good
7,946 reviews

Overall

8.0

Food

7.3

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Crew

8.5

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
4,287 reviews
Delta
8.0
Very good
7,946 reviews

Overall

8.0

Food

7.3

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Crew

8.5

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!
Finnair
7.6
Good
1,290 reviews
Delta
8.0
Very good
7,946 reviews

Overall

8.0

Food

7.3

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Crew

8.5

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
1,451 reviews
Delta
8.0
Very good
7,946 reviews

Overall

8.0

Food

7.3

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Crew

8.5

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
8,790 reviews
Delta
8.0
Very good
7,946 reviews

Overall

8.0

Food

7.3

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Crew

8.5

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. 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 one-way?

    $95 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 $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 $254). Flying from Indiana to Caribbean 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

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 junio 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$130Average$344FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$205Average$376FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$215Average$627FlexibilityNo cancel feeOn-time69%
DeltaCheapest$254Average$628FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$265Average$653FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$337Average$762FlexibilityNo cancel feeOn-time63%

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