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$65+ 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 4/14. Fares are subject to change and may not be available on all flights or dates of travel.
IND — SJU
Feb 28 — Mar 71
Fri 2/28
Fri 3/7
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 February 23, 2025.

Round-trip from

$150
(Frontier)

One-way from

$65
(Frontier)

Popular in

December

Cheapest in

September

Average price

$374
From Indiana to Caribbean
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One-way flight from Indiana to Caribbean
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($33 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($12 potential savings vs. average RT price).
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Average for round-trip flights in February 2025
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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 February 23, 2025.

This Frontier deal was found by Cheapflights users on 2/22. 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 4/287:29 pmCVG - SJU
1 stop7h 20mFrontier
Sun 5/411:20 amSJU - CVG
1 stop13h 20mFrontier
Deal found 2/22$150
This Kiwi.com deal was found by Cheapflights users on 2/22. 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 5/14:15 pmORD - SJU
1 stop9h 36mMultiple Airlines
Tue 5/610:25 amSJU - ORD
1 stop8h 16mMultiple Airlines
Deal found 2/22$167
This Cheapflightsfares deal was found by Cheapflights users on 2/22. 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.
Wed 5/146:00 amORD - SJU
1 stop17h 12mSpirit Airlines
Thu 5/298:59 pmSJU - ORD
Nonstop4h 59mSpirit Airlines
Deal found 2/22$169
This Frontier deal was found by Cheapflights users on 2/20. 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 5/21:19 pmMDW - SJU
1 stop12h 32mFrontier
Mon 5/510:46 amSJU - MDW
1 stop14h 01mFrontier
Deal found 2/20$170
This Frontier deal was found by Cheapflights users on 2/22. 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.
Sat 3/81:30 pmORD - SJU
1 stop10h 10mFrontier
Sat 3/155:25 amSJU - ORD
1 stop7h 45mFrontier
Deal found 2/22$171
This Mytrip deal was found by Cheapflights users on 2/21. 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.
Mon 4/286:00 amCVG - SJU
2 stops27h 40mMultiple Airlines
Wed 5/71:10 amSJU - CVG
2 stops35h 01mMultiple Airlines
Deal found 2/21$208
This Delta deal was found by Cheapflights users on 2/22. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/305:09 pmCVG - SJU
1 stop6h 06mDelta
Mon 5/56:35 amSJU - CVG
1 stop10h 44mDelta
Deal found 2/22$215
This American Airlines deal was found by Cheapflights users on 2/22. 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.
Tue 10/76:05 amCVG - SJU
2 stops10h 15mAmerican Airlines
Sat 10/114:05 pmSJU - CVG
1 stop6h 52mAmerican Airlines
Deal found 2/22$235
This Mytrip deal was found by Cheapflights users on 2/21. 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.
Tue 3/47:07 amORD - STT
2 stops28h 46mSpirit Airlines
Tue 3/1111:11 amSTT - ORD
2 stops25h 25mSpirit Airlines
Deal found 2/21$263
This Delta deal was found by Cheapflights users on 2/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/12:00 pmORD - SJU
1 stop7h 59mDelta
Wed 3/56:17 pmSJU - ORD
1 stop7h 32mDelta
Deal found 2/21$271
This Delta deal was found by Cheapflights users on 2/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/2512:48 pmMDW - SJU
1 stop9h 27mDelta
Mon 4/287:15 amSJU - MDW
1 stop11h 44mDelta
Deal found 2/21$271
This American Airlines deal was found by Cheapflights users on 2/21. 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.
Fri 2/286:35 pmORD - SJU
1 stop15h 14mAmerican Airlines
Mon 3/34:44 pmSJU - ORD
1 stop9h 33mAmerican Airlines
Deal found 2/21$296

Find flights from Indiana to Caribbean within your budget

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 February 23, 2025.

Fly from

Indiana

Fly to

Caribbean

Route

Depart

Return

Price

CincinnatiSan Juan

CVG - SJU

CVGSJU

Cincinnati Cinci./N. Kentucky

Mon 4/28

7:29 pm-2:49 am

1 stop7h 20m

San Juan Luis Munoz Marin Intl

Sun 5/4

11:20 am-12:40 am

1 stop13h 20m

$150

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Thu 5/1

8:45 am-2:34 am

1 stop16h 49m

San Juan Luis Munoz Marin Intl

Thu 5/8

4:46 pm-8:50 pm

Nonstop5h 04m

$167

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 3/11

9:25 am-11:38 pm

1 stop13h 13m

San Juan Luis Munoz Marin Intl

Fri 3/14

6:00 am-10:36 am

Nonstop5h 36m

$168

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Fri 5/2

1:19 pm-2:51 am

1 stop12h 32m

San Juan Luis Munoz Marin Intl

Mon 5/5

10:46 am-11:47 pm

1 stop14h 01m

$170

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 3/8

1:30 pm-1:40 am

1 stop10h 10m

San Juan Luis Munoz Marin Intl

Thu 3/13

5:45 am-6:54 pm

1 stop14h 09m

$171

CincinnatiSan Juan

CVG - SJU

CVGSJU

Cincinnati Cinci./N. Kentucky

Mon 4/28

6:00 am-9:40 am

2 stops27h 40m

San Juan Luis Munoz Marin Intl

Wed 5/7

1:10 am-12:11 pm

2 stops35h 01m

$208

CincinnatiSan Juan

CVG - SJU

CVGSJU

Cincinnati Cinci./N. Kentucky

Wed 4/30

5:09 pm-11:15 pm

1 stop6h 06m

San Juan Luis Munoz Marin Intl

Mon 5/5

6:35 am-5:19 pm

1 stop10h 44m

$215

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Tue 3/4

7:07 am-1:53 pm

2 stops28h 46m

Saint Thomas Island Cyril E King

Tue 3/11

11:11 am-11:36 am

2 stops25h 25m

$263

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 3/1

2:00 pm-11:59 pm

1 stop7h 59m

San Juan Luis Munoz Marin Intl

Wed 3/5

6:17 pm-11:49 pm

1 stop7h 32m

$271

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Fri 4/25

12:48 pm-11:15 pm

1 stop9h 27m

San Juan Luis Munoz Marin Intl

Mon 4/28

7:15 am-5:59 pm

1 stop11h 44m

$271

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/22

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.

Travel insights for flights from Indiana to Caribbean

Get recent, data-driven insights about flights from Indiana to Caribbean including ideal travel times, pricing trends, and more.

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 March is currently the most expensive (average of $363). 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 February 23, 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 February 23, 2025.
Southwest
8.1
Very good
4,396 reviews

Entertainment

7.6

Overall

8.1

Boarding

8.2

Comfort

8.1

Food

7.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Southwest
8.1
Very good
4,396 reviews
Southwest
8.1
Very good
4,396 reviews

Entertainment

7.6

Overall

8.1

Boarding

8.2

Comfort

8.1

Food

7.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Delta
8.0
Very good
8,203 reviews
Southwest
8.1
Very good
4,396 reviews

Entertainment

7.6

Overall

8.1

Boarding

8.2

Comfort

8.1

Food

7.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Alaska Airlines
8.0
Very good
9,702 reviews
Southwest
8.1
Very good
4,396 reviews

Entertainment

7.6

Overall

8.1

Boarding

8.2

Comfort

8.1

Food

7.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Copa Airlines
7.6
Good
1,500 reviews
Southwest
8.1
Very good
4,396 reviews

Entertainment

7.6

Overall

8.1

Boarding

8.2

Comfort

8.1

Food

7.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

United Airlines
7.4
Good
8,754 reviews
Southwest
8.1
Very good
4,396 reviews

Entertainment

7.6

Overall

8.1

Boarding

8.2

Comfort

8.1

Food

7.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

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?

    $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 American Airlines, with prices starting from $81 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 $254). Flying from Indiana to Caribbean in March is currently the most expensive (average of $363). 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 February 23, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$130Average$268FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$179Average$365FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$254Average$657FlexibilityNo cancel feeOn-time69%
DeltaCheapest$254Average$659FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$267Average$697FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$350Average$818FlexibilityNo cancel feeOn-time63%
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