Latest deals
Insights
FAQs
Reviews
Price Alerts

Cheap flights from Indiana to Caribbean Islands from $77

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Indiana to Caribbean Islands departing on 2/28. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Find the cheapest flights from Indiana to Caribbean Islands

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
5:50 am - 4:21 pm
ORD
-
SJU
8h 31m1 stop
Multiple Airlines Logo
1:22 pm - 4:37 pm
SJU
-
ORD
5h 15mnonstop
$192Multiple Airlines
Sat, Jan 10 - Tue, Jan 13
Multiple Airlines Logo
6:57 pm - 3:06 pm
ORD
-
SJU
18h 09m1 stop
Multiple Airlines Logo
8:53 pm - 9:39 am
SJU
-
ORD
14h 46m1 stop
$193Multiple Airlines
Sun, Feb 8 - Sat, Feb 21
Spirit Airlines Logo
9:23 am - 6:58 pm
ORD
-
SJU
7h 35m1 stop
Spirit Airlines Logo
11:52 am - 6:16 pm
SJU
-
ORD
8h 24m1 stop
$194Spirit Airlines
Sun, Jan 18 - Thu, Jan 22
Multiple Airlines Logo
9:18 am - 6:58 pm
ORD
-
SJU
7h 40m1 stop
Multiple Airlines Logo
3:53 am - 3:52 pm
SJU
-
ORD
13h 59m1 stop
$195Multiple Airlines
Sat, Feb 28 - Tue, Mar 3
JetBlue Logo
7:45 am - 6:07 pm
ORD
-
SJU
8h 22m1 stop
JetBlue Logo
10:25 am - 7:36 pm
SJU
-
ORD
11h 11m1 stop
$196JetBlue
Tue, Jan 20 - Sat, Jan 24
Spirit Airlines Logo
12:17 pm - 6:49 pm
ORD
-
SJU
4h 32mnonstop
Spirit Airlines Logo
12:32 pm - 3:48 pm
SJU
-
ORD
5h 16mnonstop
$197Spirit Airlines
Tue, Feb 17 - Thu, Feb 26
Multiple Airlines Logo
12:17 pm - 6:49 pm
ORD
-
SJU
4h 32mnonstop
Multiple Airlines Logo
3:53 am - 3:52 pm
SJU
-
ORD
13h 59m1 stop
$198Multiple Airlines
Tue, Feb 17 - Mon, Feb 23
Frontier Logo
9:22 pm - 9:54 am
MDW
-
SJU
10h 32m1 stop
Frontier Logo
3:22 pm - 10:19 pm
SJU
-
MDW
7h 57m1 stop
$199Frontier
Mon, Mar 2 - Mon, Mar 9
Frontier Logo
6:10 am - 3:19 pm
MDW
-
SJU
7h 09m1 stop
Frontier Logo
4:35 pm - 10:19 pm
SJU
-
MDW
7h 44m1 stop
$200Frontier
Thu, Jan 8 - Wed, Jan 14
United Airlines Logo
5:55 pm - 6:11 am
CVG
-
SJU
11h 16m2 stops
United Airlines Logo
7:45 am - 3:47 pm
SJU
-
CVG
9h 02m1 stop
$225United Airlines
Fri, Jan 23 - Tue, Jan 27

United Airlines flights from Indiana to Caribbean Islands

Our best United Airlines deals on Indiana to Caribbean Islands flight tickets
United Airlines
Jan 23
CVG5:55 pmCincinnati Cinci./N. Kentucky
11h 16m
2 stops
SJU6:11 amSan Juan Luis Munoz Marin Intl
Jan 27
SJU7:45 amSan Juan Luis Munoz Marin Intl
9h 02m
1 stop
CVG3:47 pmCincinnati Cinci./N. Kentucky
$225
Find similar
United Airlines
Jan 3
IND11:20 amIndianapolis
10h 02m
2 stops
SJU10:22 pmSan Juan Luis Munoz Marin Intl
Jan 31
SJU4:52 pmSan Juan Luis Munoz Marin Intl
7h 38m
1 stop
IND11:30 pmIndianapolis
$300
Find similar
United Airlines
Jan 8
IND11:25 amIndianapolis
9h 57m
2 stops
SJU10:22 pmSan Juan Luis Munoz Marin Intl
Jan 13
SJU7:45 amSan Juan Luis Munoz Marin Intl
9h 12m
1 stop
IND3:57 pmIndianapolis
$305
Find similar

JetBlue flights from Indiana to Caribbean Islands

Our best JetBlue deals on Indiana to Caribbean Islands flight tickets
JetBlue
Jan 20
ORD7:45 amChicago O'Hare Intl
8h 22m
1 stop
SJU6:07 pmSan Juan Luis Munoz Marin Intl
Jan 31
SJU1:20 pmSan Juan Luis Munoz Marin Intl
8h 16m
1 stop
ORD7:36 pmChicago O'Hare Intl
$196
Find similar
JetBlue
Jan 6
ORD10:55 amChicago O'Hare Intl
11h 19m
1 stop
SJU12:14 amSan Juan Luis Munoz Marin Intl
Jan 13
SJU11:06 amSan Juan Luis Munoz Marin Intl
10h 30m
1 stop
ORD7:36 pmChicago O'Hare Intl
$202
Find similar
JetBlue
Jan 23
ORD7:45 amChicago O'Hare Intl
8h 20m
1 stop
SJU6:05 pmSan Juan Luis Munoz Marin Intl
Jan 31
SJU1:20 pmSan Juan Luis Munoz Marin Intl
8h 16m
1 stop
ORD7:36 pmChicago O'Hare Intl
$205
Find similar

momondo Fare Finder

 
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, momondo users made 832,500 searches. Data last updated December 28, 2025.
Use the filters below to find and compare flights from Indiana to Caribbean Islands that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 1/10

5:50 am-4:21 pm

1 stop8h 31m

San Juan Luis Munoz Marin Intl

Tue 1/13

1:22 pm-4:37 pm

Nonstop5h 15m

$192

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sun 2/8

6:57 pm-3:06 pm

1 stop18h 09m

San Juan Luis Munoz Marin Intl

Sat 2/21

8:53 pm-9:39 am

1 stop14h 46m

$193

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sun 1/18

9:23 am-6:58 pm

1 stop7h 35m

San Juan Luis Munoz Marin Intl

Thu 1/22

11:52 am-6:16 pm

1 stop8h 24m

$194

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 2/28

9:18 am-6:58 pm

1 stop7h 40m

San Juan Luis Munoz Marin Intl

Tue 3/3

3:53 am-3:52 pm

1 stop13h 59m

$195

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 1/20

7:45 am-6:07 pm

1 stop8h 22m

San Juan Luis Munoz Marin Intl

Sat 1/24

10:25 am-7:36 pm

1 stop11h 11m

$196

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 2/17

12:17 pm-6:49 pm

Nonstop4h 32m

San Juan Luis Munoz Marin Intl

Thu 2/26

12:32 pm-3:48 pm

Nonstop5h 16m

$197

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 2/17

12:17 pm-6:49 pm

Nonstop4h 32m

San Juan Luis Munoz Marin Intl

Mon 2/23

3:53 am-3:52 pm

1 stop13h 59m

$198

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Mon 3/2

9:22 pm-9:54 am

1 stop10h 32m

San Juan Luis Munoz Marin Intl

Mon 3/9

3:22 pm-10:19 pm

1 stop7h 57m

$199

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Thu 1/8

6:10 am-3:19 pm

1 stop7h 09m

San Juan Luis Munoz Marin Intl

Wed 1/14

4:35 pm-10:19 pm

1 stop7h 44m

$200

CincinnatiSan Juan

CVG - SJU

CVGSJU

Cincinnati Cinci./N. Kentucky

Fri 1/23

5:55 pm-6:11 am

2 stops11h 16m

San Juan Luis Munoz Marin Intl

Tue 1/27

7:45 am-3:47 pm

1 stop9h 02m

$225

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

See travel insights to Caribbean Islands from

How to get the cheapest flight ticket from Indiana to Caribbean Islands

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Caribbean Islands?

The month of September is, on average, the cheapest month to fly to Caribbean Islands from Indiana, with most prices found around $270. The month of April is another great option to travel to Caribbean Islands, with average flight prices from Indiana averaging around $355.

What is the cheapest day to depart on your flight to Caribbean Islands?

The cheapest day to depart from Indiana to Caribbean Islands is on a Tuesday. Travelers who choose to depart for Caribbean Islands on a Tuesday will often find tickets for as low as $362. If your travel schedule is flexible, try to avoid departing on a Sunday because tickets tend to average around $494. These prices are subject to change though, so be sure to set up a Price Alert for flights to Caribbean Islands.

What is the cheapest time of day to depart on your flight to Caribbean Islands?

According to our data, the cheapest time of day to fly to Caribbean Islands is in the evening. momondo users have found flights departing from Indiana to Caribbean Islands in the evening for as low as $304. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. Try not to purchase tickets in the afternoon because they tend to be around $396. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Indiana to Caribbean Islands flight route?

Fly from Indianapolis to Punta Cana for the best Indiana - Caribbean Islands flight prices

How far in advance should I book a flight to Caribbean Islands?

You are more likely to see cheaper flights to Caribbean Islands from Indiana when booking weeks ahead of your departure date. In general, you can expect to find flights to Caribbean Islands for around $398 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Caribbean Islands from Indiana for as low as $337 on momondo.

What cabin class options are available on Indiana to Caribbean Islands flights?

There is only 1 cabin class available to choose from on Indiana to Caribbean Islands flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Indiana to Caribbean Islands flights?

No. A direct flight is the cheapest option for a flight between Indiana to Caribbean Islands.

Cheap Indiana to Caribbean Islands flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Indiana to Caribbean Islands

Fastest flight time

3h 22m

Direct flights

Every day

Airports in Caribbean Islands

99 airports
The fastest flight from Indiana to Caribbean Islands takes 3h 22m
Direct flights go from Indiana to Caribbean Islands every day.
There are 99 airports in Caribbean Islands. From Indiana there are direct flights to Nassau Intl (NAS), Montego Bay Sangster Intl (MBJ).
Search flight deals

  • When did momondo last update prices for flights from Indiana to Caribbean Islands?

    Prices for flights from Indiana to Caribbean Islands are refreshed on a daily basis.

  • How many operators does momondo search for flights from Indiana to Caribbean Islands?

  • How old do you have to be to fly from Indiana to Caribbean Islands?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Indiana to Caribbean Islands.

  • What documentation or ID do you need to fly to Caribbean Islands?

    The travel and health documents you'll need for your trip to Caribbean Islands may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Caribbean Islands. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Indiana to Caribbean Islands?

Best airlines flying from Indiana to Caribbean Islands

Compare and see reviews for airlines that fly from Indiana to Caribbean Islands with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $130Free CancellationRating
5.7
3,064 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $191Free CancellationRating
6.3
8,210 reviews
Search Spirit Airlines flights
SouthwestPriceFrom $215Free CancellationRating
8.0
4,256 reviews
Search Southwest flights
United AirlinesPriceFrom $215Free CancellationRating
7.4
9,114 reviews
Search United Airlines flights
DeltaPriceFrom $215Free CancellationRating
7.9
8,017 reviews
Search Delta flights
American AirlinesPriceFrom $265Free CancellationRating
7.2
11,070 reviews
Search American Airlines flights

Why use momondo?

Why should I use momondo to find a flight deal from Indiana to Caribbean Islands?

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Indiana to Caribbean Islands. Millions of users trust and use momondo every year so you are in good hands.

Can I find flights from Indiana to Caribbean Islands with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Caribbean Islands from Indiana with this policy.

How can momondo help me find flights from Indiana to Caribbean Islands?

momondo provides multiple filters to help you find the best flight to Caribbean Islands from Indiana. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Indiana to Caribbean Islands right now. Can momondo alert me if prices change?

If you are not ready to book a flight from Indiana to Caribbean Islands now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Caribbean Islands and let you know when they change.

An easier way to manage your Caribbean Islands trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Tue 1/27
Tue 2/3
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Caribbean Islands

Popular cities in Caribbean Islands

Popular flights according to clicks in the last 7 days on momondo
Flights to New Yorkfrom $50
Flights to Londonfrom $344
Flights to Bangkokfrom $536
Flights to Tokyofrom $463
Flights to Los Angelesfrom $47
Flights to Parisfrom $352
Flights to Copenhagenfrom $365
Flights to Istanbulfrom $422
Flights to Manilafrom $540
Flights to Romefrom $356
Flights to Miamifrom $50
Flights to Chicagofrom $51