Indiana

$87+ Cheap flights from Caribbean to Indiana

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 2/24. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — IND
feb. 25 — mar. 41
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Caribbean to Indiana with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Caribbean to Indiana

Cheapest flights from Caribbean to Indiana
Explore the most affordable flight options available from Caribbean to Indiana. Find the lowest fares from popular airlines and budget airlines, with prices last updated on enero 26, 2026.

This Trip.com deal was found by Cheapflights users on 1/25. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 3/55:01 am
SJU
-
ORD
1 stop8h 48m
JetBlue
lun. 3/912:41 pm
ORD
-
SJU
1 stop7h 43m
JetBlue
Deal found 1/25$120
This Trip.com deal was found by Cheapflights users on 1/25. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 2/273:05 pm
SJU
-
ORD
1 stop9h 54m
JetBlue
lun. 3/212:41 pm
ORD
-
SJU
1 stop9h 48m
JetBlue
Deal found 1/25$137
This Trip.com deal was found by Cheapflights users on 1/26. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 2/119:25 am
SJU
-
ORD
1 stop12h 06m
JetBlue
mié. 2/1810:00 am
ORD
-
SJU
1 stop10h 53m
JetBlue
Deal found 1/26$142
This Trip.com deal was found by Cheapflights users on 1/25. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 2/243:53 am
SJU
-
ORD
1 stop13h 59m
Multiple Airlines
mié. 3/410:00 am
ORD
-
SJU
1 stop10h 03m
Multiple Airlines
Deal found 1/25$145
This Trip.com deal was found by Cheapflights users on 1/25. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 4/2311:25 pm
SJU
-
ORD
1 stop10h 26m
JetBlue
mar. 4/288:31 am
ORD
-
SJU
1 stop8h 59m
JetBlue
Deal found 1/25$146
This Trip.com deal was found by Cheapflights users on 1/25. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 3/61:44 pm
SJU
-
ORD
1 stop11h 16m
JetBlue
mar. 3/1012:39 pm
ORD
-
SJU
1 stop7h 45m
JetBlue
Deal found 1/25$148
This Trip.com deal was found by Cheapflights users on 1/24. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 3/612:32 pm
SJU
-
ORD
Nonstop5h 16m
Multiple Airlines
mar. 3/1012:39 pm
ORD
-
SJU
1 stop7h 45m
Multiple Airlines
Deal found 1/24$153
This Trip.com deal was found by Cheapflights users on 1/23. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 4/3011:59 pm
SJU
-
ORD
1 stop10h 49m
JetBlue
dom. 5/36:00 am
ORD
-
SJU
1 stop9h 47m
JetBlue
Deal found 1/23$157
This JetBlue deal was found by Cheapflights users on 1/24. 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.
sáb. 5/211:20 pm
SJU
-
ORD
1 stop10h 31m
JetBlue
mié. 5/63:15 pm
ORD
-
SJU
1 stop9h 52m
JetBlue
Deal found 1/24$160
This eDestinos deal was found by Cheapflights users on 1/24. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 2/185:25 pm
SJU
-
ORD
1 stop19h 21m
Frontier
lun. 3/22:13 pm
ORD
-
SJU
1 stop10h 12m
Frontier
Deal found 1/24$161
This Priceline deal was found by Cheapflights users on 1/25. 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.
mié. 2/185:25 pm
SJU
-
MDW
1 stop23h 01m
Frontier
mar. 2/246:10 am
MDW
-
SJU
1 stop6h 56m
Frontier
Deal found 1/25$174
This Frontier deal was found by Cheapflights users on 1/23. 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.
jue. 2/266:00 am
SJU
-
CVG
1 stop11h 37m
Frontier
lun. 3/27:14 pm
CVG
-
SJU
1 stop6h 39m
Frontier
Deal found 1/23$182

Find flight deals from Caribbean to Indiana

Keep the following information in mind while searching for Caribbean to Indiana flight deals. Data was last updated enero 26, 2026.

Round-trip from

$120
(Trip.com)

One-way from

$87
(Frontier)

Popular in

March

Cheapest in

January

Average price

$235
From Caribbean to Indiana
One-way flight from Caribbean to Indiana
Highest demand for flights based on searches. 6% potential increase in price ($27 potential increase over avg. RT price).
Cheapest flight prices on average. 2% potential price decrease ($9 potential savings vs. average RT price).
Average for round-trip flights in January 2026

Cheapflights Fare Finder

 
Customize your flight search to find flights from Caribbean to Indiana 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 26, 2026.
Use the filters below to find and compare flights from Caribbean to Indiana that are best for you.

Fly from

Caribbean

Fly to

Indiana

Route

Depart

Return

Price

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

vie. 5/1

11:59 pm-9:48 am

1 stop10h 49m

Chicago O'Hare Intl

lun. 5/4

3:15 pm-2:07 am

1 stop9h 52m

$169

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

mié. 4/29

11:59 pm-9:48 am

1 stop10h 49m

Chicago O'Hare Intl

lun. 5/4

3:15 pm-2:07 am

1 stop9h 52m

$169

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

lun. 5/4

11:25 pm-8:51 am

1 stop10h 26m

Chicago O'Hare Intl

jue. 5/7

10:35 am-9:01 pm

1 stop9h 26m

$171

San JuanCincinnati

SJU - CVG

SJUCVG

San Juan Luis Munoz Marin Intl

jue. 2/26

6:00 am-4:37 pm

1 stop11h 37m

Cincinnati Cinci./N. Kentucky

lun. 3/2

7:14 pm-2:53 am

1 stop6h 39m

$182

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

jue. 2/26

6:00 am-1:56 pm

1 stop9h 56m

Chicago Midway

lun. 3/2

9:22 pm-9:54 am

1 stop10h 32m

$182

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

sáb. 5/2

11:59 pm-9:48 am

1 stop10h 49m

Chicago O'Hare Intl

mié. 5/6

3:15 pm-12:07 am

1 stop7h 52m

$183

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

jue. 2/12

12:32 pm-3:48 pm

Nonstop5h 16m

Chicago O'Hare Intl

dom. 2/15

12:17 pm-6:49 pm

Nonstop4h 32m

$187

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

jue. 4/9

11:00 am-9:33 pm

1 stop11h 33m

Chicago O'Hare Intl

lun. 4/13

10:00 am-10:01 pm

1 stop11h 01m

$191

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

vie. 2/27

5:10 am-11:54 am

1 stop8h 44m

Chicago O'Hare Intl

lun. 3/2

12:41 pm-12:29 am

1 stop9h 48m

$192

San JuanCincinnati

SJU - CVG

SJUCVG

San Juan Luis Munoz Marin Intl

jue. 2/19

4:25 pm-12:59 am

1 stop9h 34m

Cincinnati Cinci./N. Kentucky

mié. 2/25

3:20 pm-12:43 am

1 stop8h 23m

$203

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/26

Showing 1-10 of 60 results
1
2
3
...
6

Best time to book a flight from Caribbean to Indiana

Have a flexible travel schedule? Discover the best time to fly to Indiana from Caribbean 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 Caribbean to Indiana

What is the cheapest month to book a flight from Caribbean to Indiana?

Currently, December is the cheapest month in which you can book a flight from Caribbean to Indiana (average of $109). Flying from Caribbean to Indiana in July is currently the most expensive (average of $264). 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 CB to IN?

Find hourly flight availability from Caribbean to Indiana. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated enero 26, 2026.

When flying from Caribbean to Indiana, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Reviews of airlines servicing Indiana

Get insights into the airlines that provide service to Indiana. 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 Indiana. Reviews last updated enero 26, 2026.
Peruse reviews from past customers who have flown with Southwest, Delta, and United Airlines from Caribbean to Indiana to help guide your decision. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.

Crew

8.6

Boarding

8.1

Overall

8.0

Comfort

8.0

Food

7.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

Crew

8.6

Boarding

8.1

Overall

8.0

Comfort

8.0

Food

7.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

Crew

8.6

Boarding

8.1

Overall

8.0

Comfort

8.0

Food

7.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

Crew

8.6

Boarding

8.1

Overall

8.0

Comfort

8.0

Food

7.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

Crew

8.6

Boarding

8.1

Overall

8.0

Comfort

8.0

Food

7.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

Crew

8.6

Boarding

8.1

Overall

8.0

Comfort

8.0

Food

7.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

Related info for your journey

Find useful and relevant information for your journey from Caribbean to Indiana. 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 Caribbean to Indiana?

    Airlines like JetBlue, Frontier, and American Airlines fly from Caribbean to Indiana in about 10h 49m. The time it takes to get you to your destination can typically vary by up to 7h 10m. The distance from Caribbean to Indiana is about 2073 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

    One-way options have recently been found by users for as low as $108 on Delta. Other airlines that offer cheap prices include Southwest from $112 and American Airlines from $118 one-way.

  • Can I find deals for flights from Caribbean to Indiana that include hotel bookings?

    Yes. In addition to deals on Caribbean to Indiana flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Caribbean to Indiana?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Caribbean to Indiana.

  • Can I find deals for business class flights from Caribbean to Indiana?

    Yes. Cheapflights offers flight deals from Caribbean to Indiana 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 Caribbean to Indiana?

    Currently, December is the cheapest month in which you can book a flight from Caribbean to Indiana (average of $109). Flying from Caribbean to Indiana in July is currently the most expensive (average of $264). 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 Caribbean to Indiana

See prices for flight routes from nearby airports that may be better suited for you.

Top 6 airlines flying from Caribbean to Indiana

Discover the top 6 airlines that operate flights from Caribbean to Indiana. 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 26, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$118Average$467FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$214Average$305FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$215Average$355FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$232Average$378FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$235Average$551FlexibilityNo cancel feeOn-time71%
Spirit AirlinesCheapest$326Average$429FlexibilityNo cancel feeOn-time65%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.