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Caribbean Islands

$65+ 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 4/14. Fares are subject to change and may not be available on all flights or dates of travel.
IND — SJU
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
1 adult, Economy
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Cheap 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 February 20, 2025.

Round-trip from

$147
(CheapOair)

One-way from

$65
(Frontier)

Popular in

December

Cheapest in

September

Average price

$374
From Indiana to Caribbean Islands
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One-way flight from Indiana to Caribbean Islands
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 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 February 20, 2025.

This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/115:15 amCVG - SJU
1 stop18h 23mFrontier
Tue 3/189:35 pmSJU - CVG
1 stop16h 16mFrontier
Deal found 2/20$147
This Booking.com 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/105:05 amORD - SJU
1 stop18h 10mMultiple Airlines
Sat 3/156:00 amSJU - ORD
Nonstop5h 36mMultiple Airlines
Deal found 2/20$168
This Mytrip deal was found by Cheapflights users on 2/19. 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 3/54:20 pmMDW - SJU
1 stop26h 50mFrontier
Tue 3/116:00 amSJU - MDW
1 stop10h 32mFrontier
Deal found 2/19$168
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/1410:00 amORD - SJU
Nonstop4h 51mSpirit Airlines
Fri 5/304:46 pmSJU - ORD
Nonstop5h 04mSpirit Airlines
Deal found 2/20$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.
Sat 3/81:30 pmORD - SJU
1 stop10h 10mFrontier
Thu 3/135:45 amSJU - ORD
1 stop14h 09mFrontier
Deal found 2/20$171
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/286:00 amCVG - SJU
1 stop10h 37mMultiple Airlines
Wed 5/71:10 amSJU - CVG
2 stops35h 01mMultiple Airlines
Deal found 2/20$188
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/275:52 amCVG - SJU
2 stops8h 43mAmerican Airlines
Thu 5/111:45 amSJU - CVG
1 stop12h 26mAmerican Airlines
Deal found 2/20$235
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/1610:45 amCVG - SJU
1 stop8h 49mDelta
Sat 5/247:30 amSJU - CVG
1 stop6h 51mDelta
Deal found 2/20$250
This Kiwi.com deal was found by Cheapflights users on 2/19. 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 3/199:08 pmORD - STT
1 stop10h 47mSpirit Airlines
Tue 3/259:50 amSTT - ORD
1 stop10h 06mSpirit Airlines
Deal found 2/19$262
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/1011:30 amORD - SJU
1 stop7h 40mDelta
Wed 3/192:42 pmSJU - ORD
1 stop7h 16mDelta
Deal found 2/20$271
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/1112:51 pmMDW - SJU
1 stop9h 16mDelta
Tue 3/1812:54 pmSJU - MDW
1 stop10h 29mDelta
Deal found 2/20$271
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/286:35 pmORD - SJU
1 stop9h 37mUnited Airlines
Sat 3/12:05 amSJU - ORD
1 stop9h 00mUnited Airlines
Deal found 2/20$296

Find flights from Indiana to Caribbean Islands within your budget

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 February 20, 2025.

Fly from

Indiana

Fly to

Caribbean Islands

Route

Depart

Return

Price

CincinnatiSan Juan

CVG - SJU

CVGSJU

Cincinnati Cinci./N. Kentucky

Tue 3/11

5:15 am-11:38 pm

1 stop18h 23m

San Juan Luis Munoz Marin Intl

Tue 3/18

9:35 pm-1:51 pm

1 stop16h 16m

$147

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mon 3/10

5:05 am-12:15 am

1 stop18h 10m

San Juan Luis Munoz Marin Intl

Sat 3/15

6:00 am-10:36 am

Nonstop5h 36m

$168

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Wed 3/5

4:20 pm-9:10 pm

1 stop26h 50m

San Juan Luis Munoz Marin Intl

Tue 3/11

6:00 am-3:32 pm

1 stop10h 32m

$168

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Wed 5/14

10:00 am-3:51 pm

Nonstop4h 51m

San Juan Luis Munoz Marin Intl

Fri 5/30

4:46 pm-8:50 pm

Nonstop5h 04m

$169

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-4:37 pm

1 stop10h 37m

San Juan Luis Munoz Marin Intl

Wed 5/7

1:10 am-12:11 pm

2 stops35h 01m

$188

CincinnatiSan Juan

CVG - SJU

CVGSJU

Cincinnati Cinci./N. Kentucky

Sun 4/27

5:52 am-2:35 pm

2 stops8h 43m

San Juan Luis Munoz Marin Intl

Thu 5/1

11:45 am-12:11 am

1 stop12h 26m

$235

CincinnatiSan Juan

CVG - SJU

CVGSJU

Cincinnati Cinci./N. Kentucky

Fri 5/16

10:45 am-7:34 pm

1 stop8h 49m

San Juan Luis Munoz Marin Intl

Sat 5/24

7:30 am-2:21 pm

1 stop6h 51m

$250

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Wed 3/19

9:08 pm-8:55 am

1 stop10h 47m

Saint Thomas Island Cyril E King

Tue 3/25

9:50 am-6:56 pm

1 stop10h 06m

$262

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mon 3/10

11:30 am-8:10 pm

1 stop7h 40m

San Juan Luis Munoz Marin Intl

Wed 3/19

2:42 pm-8:58 pm

1 stop7h 16m

$271

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/20

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.

Travel insights for flights from Indiana to Caribbean Islands

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

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 $254). Flying from Indiana to Caribbean Islands 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 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 February 20, 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.

Rainfall in Caribbean Islands by month

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

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

Temperature in Caribbean Islands by month

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

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

Get insights into the airlines that provide service to Caribbean Islands. 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 Islands. Reviews last updated February 20, 2025.
To help decide which airline to fly from Indiana to Caribbean Islands, see what other customers have to say about Southwest, Alaska Airlines and Delta. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Overall

8.1

Boarding

8.2

Entertainment

7.6

Food

7.1

Comfort

8.1

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
4,411 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Overall

8.1

Boarding

8.2

Entertainment

7.6

Food

7.1

Comfort

8.1

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
9,697 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Overall

8.1

Boarding

8.2

Entertainment

7.6

Food

7.1

Comfort

8.1

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
8,219 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Overall

8.1

Boarding

8.2

Entertainment

7.6

Food

7.1

Comfort

8.1

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.

SWISS
7.5
Good
1,568 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Overall

8.1

Boarding

8.2

Entertainment

7.6

Food

7.1

Comfort

8.1

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
8,765 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Overall

8.1

Boarding

8.2

Entertainment

7.6

Food

7.1

Comfort

8.1

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 Islands. 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 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 $83 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 $254). Flying from Indiana to Caribbean Islands 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 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 February 20, 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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