What airlines fly to Caribbean?

American Airlines, Delta and Southwest are the top three most popular airlines that fly to Caribbean from Evansville according to our data. American Airlines is the first choice among our users, with 54% of people opting to fly with this airline when traveling to Caribbean. Keep in mind that there are 5 different airlines that fly to Caribbean on a routine basis, so you have a few additional options to choose from.

What is the cheapest airline that flies from Evansville Dress Regional to Caribbean?

Delta, American Airlines, and WestJet are the most popular carriers operating from Evansville Dress Regional to Caribbean

When did momondo last update prices for flights from Evansville Dress Regional Airport to Caribbean?

Prices for flights from Evansville Dress Regional Airport to Caribbean were last updated today.

How many operators does momondo search for flights from Evansville Dress Regional Airport to Caribbean?

As of February 2026, there are 2 operators available to choose from for flights from Evansville Dress Regional Airport to Caribbean.

How old do you have to be to fly from Evansville Dress Regional Airport to Caribbean?

Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Evansville Dress Regional Airport to Caribbean.

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

The required travel and health documents for your Caribbean trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Caribbean. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

$133 Cheap Flights from Evansville to Caribbean in 2026

1 adult

0 bags

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

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

Trusted and free

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

Price Alerts

Not ready to book? to track prices.

Search flight deals

Find the cheapest flights from Evansville to Caribbean

Round-trip

One-way

Cheap round-trip flights

Enter your travel dates to find the best prices.

6:56 pm - 12:29 pm

EVV

SJU

16h 33m

2 stops

7:25 am - 10:58 pm

SJU

EVV

16h 33m

1 stop

$299American Airlines

Mon, May 4 - Tue, May 19

4:33 pm - 11:03 am

EVV

SJU

17h 30m

2 stops

12:59 am - 5:59 pm

SJU

EVV

18h 00m

1 stop

$306American Airlines

Mon, Jun 8 - Sat, Jun 13

6:56 pm - 11:24 am

EVV

MBJ

16h 28m

1 stop

1:15 pm - 11:54 pm

MBJ

EVV

10h 39m

1 stop

$312American Airlines

Sat, Apr 25 - Wed, Apr 29

4:13 pm - 11:51 am

EVV

MBJ

19h 38m

2 stops

12:56 pm - 10:35 am

MBJ

EVV

21h 39m

2 stops

$317American Airlines

Sat, Apr 25 - Wed, Apr 29

7:46 pm - 8:49 am

EVV

SJU

12h 03m

1 stop

7:05 pm - 3:49 pm

SJU

EVV

21h 44m

1 stop

$325Multiple Airlines

Mon, May 4 - Tue, May 19

6:01 pm - 10:56 am

EVV

SJU

15h 55m

2 stops

4:25 pm - 11:46 pm

SJU

EVV

8h 21m

1 stop

$339American Airlines

Tue, Mar 17 - Tue, Mar 24

5:30 pm - 4:35 am

EVV

SJU

10h 05m

1 stop

12:59 am - 6:01 pm

SJU

EVV

18h 02m

1 stop

$345American Airlines

Sun, May 24 - Fri, May 29

6:56 pm - 10:48 am

EVV

SJU

14h 52m

1 stop

7:25 am - 10:58 pm

SJU

EVV

16h 33m

1 stop

$372American Airlines

Thu, May 14 - Tue, May 19

7:07 am - 10:58 pm

EVV

SJU

14h 51m

2 stops

5:28 am - 3:49 pm

SJU

EVV

11h 21m

1 stop

$378American Airlines

Tue, Mar 17 - Tue, Mar 24

11:19 am - 12:49 pm

EVV

MBJ

49h 30m

2 stops

1:50 pm - 5:18 pm

MBJ

EVV

27h 28m

2 stops

$1,884WestJet

Sat, Mar 28 - Sat, Apr 4

American Airlines flights from Evansville to Caribbean

Our best American Airlines deals on Evansville to Caribbean flight tickets

American Airlines

May 2

EVV6:56 pmEvansville Dress Regional

16h 33m

2 stops

SJU12:29 pmSan Juan Luis Munoz Marin Intl

May 9

SJU11:43 amSan Juan Luis Munoz Marin Intl

12h 45m

2 stops

EVV11:28 pmEvansville Dress Regional

$299

American Airlines

Jun 8

EVV4:33 pmEvansville Dress Regional

17h 30m

2 stops

SJU11:03 amSan Juan Luis Munoz Marin Intl

Jun 13

SJU12:59 amSan Juan Luis Munoz Marin Intl

18h 00m

1 stop

EVV5:59 pmEvansville Dress Regional

$306

American Airlines

Apr 25

EVV6:56 pmEvansville Dress Regional

16h 28m

1 stop

MBJ11:24 amMontego Bay Sangster Intl

Apr 29

MBJ1:15 pmMontego Bay Sangster Intl

10h 39m

1 stop

EVV11:54 pmEvansville Dress Regional

$312

Delta flights from Evansville to Caribbean

Our best Delta deals on Evansville to Caribbean flight tickets

Delta

May 2

EVV3:00 pmEvansville Dress Regional

7h 13m

1 stop

SJU11:13 pmSan Juan Luis Munoz Marin Intl

May 9

SJU7:30 amSan Juan Luis Munoz Marin Intl

7h 26m

1 stop

EVV1:56 pmEvansville Dress Regional

$330

Delta

Mar 5

EVV11:14 amEvansville Dress Regional

7h 58m

1 stop

SJU9:12 pmSan Juan Luis Munoz Marin Intl

Mar 8

SJU7:30 amSan Juan Luis Munoz Marin Intl

10h 48m

1 stop

EVV5:18 pmEvansville Dress Regional

$863

Delta

Mar 5

EVV6:00 amEvansville Dress Regional

9h 27m

1 stop

SJU5:27 pmSan Juan Luis Munoz Marin Intl

Mar 8

SJU7:30 amSan Juan Luis Munoz Marin Intl

10h 48m

1 stop

EVV5:18 pmEvansville Dress Regional

$920

Fly from

Fly to

Route

Depart

Return

Price

EvansvilleSan Juan

EVV - SJU

EVVSJU

Evansville Dress Regional

Mon 5/4

6:56 pm-12:29 pm

2 stops16h 33m

San Juan Luis Munoz Marin Intl

Tue 5/19

7:25 am-10:58 pm

1 stop16h 33m

$299

EvansvilleSan Juan

EVV - SJU

EVVSJU

Evansville Dress Regional

Mon 6/8

4:33 pm-11:03 am

2 stops17h 30m

San Juan Luis Munoz Marin Intl

Sat 6/13

12:59 am-5:59 pm

1 stop18h 00m

$306

EvansvilleMontego Bay

EVV - MBJ

EVVMBJ

Evansville Dress Regional

Sat 4/25

6:56 pm-11:24 am

1 stop16h 28m

Montego Bay Sangster Intl

Wed 4/29

1:15 pm-11:54 pm

1 stop10h 39m

$312

EvansvilleMontego Bay

EVV - MBJ

EVVMBJ

Evansville Dress Regional

Sat 4/25

4:13 pm-11:51 am

2 stops19h 38m

Montego Bay Sangster Intl

Wed 4/29

12:56 pm-10:35 am

2 stops21h 39m

$317

EvansvilleSan Juan

EVV - SJU

EVVSJU

Evansville Dress Regional

Mon 5/4

7:46 pm-8:49 am

1 stop12h 03m

San Juan Luis Munoz Marin Intl

Tue 5/19

7:05 pm-3:49 pm

1 stop21h 44m

$325

EvansvilleSan Juan

EVV - SJU

EVVSJU

Evansville Dress Regional

Tue 3/17

6:01 pm-10:56 am

2 stops15h 55m

San Juan Luis Munoz Marin Intl

Tue 3/24

4:25 pm-11:46 pm

1 stop8h 21m

$339

EvansvilleSan Juan

EVV - SJU

EVVSJU

Evansville Dress Regional

Sun 5/24

5:30 pm-4:35 am

1 stop10h 05m

San Juan Luis Munoz Marin Intl

Fri 5/29

12:59 am-6:01 pm

1 stop18h 02m

$345

EvansvilleSan Juan

EVV - SJU

EVVSJU

Evansville Dress Regional

Thu 5/14

6:56 pm-10:48 am

1 stop14h 52m

San Juan Luis Munoz Marin Intl

Tue 5/19

7:25 am-10:58 pm

1 stop16h 33m

$372

EvansvilleSan Juan

EVV - SJU

EVVSJU

Evansville Dress Regional

Tue 3/17

7:07 am-10:58 pm

2 stops14h 51m

San Juan Luis Munoz Marin Intl

Tue 3/24

5:28 am-3:49 pm

1 stop11h 21m

$378

EvansvilleMontego Bay

EVV - MBJ

EVVMBJ

Evansville Dress Regional

Sat 3/28

11:19 am-12:49 pm

2 stops49h 30m

Montego Bay Sangster Intl

Sat 4/4

1:50 pm-5:18 pm

2 stops27h 28m

$1,884

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from Evansville to Caribbean

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

Prices

Airlines

Can stopping save me money on Evansville to Caribbean flights?

You could potentially save up to 9% on your flight if you consider stops on a Evansville to Caribbean flight.

Cheap Evansville to Caribbean flight deals and tips

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

Fastest flight time	6h 41m
Direct flights	None

The fastest flight from Evansville to Caribbean takes 6h 41m

There are no direct flights from Evansville to Caribbean. There are no popular flight routes from Evansville to Caribbean.

Search flight deals

When did momondo last update prices for flights from Evansville Dress Regional Airport to Caribbean?
Prices for flights from Evansville Dress Regional Airport to Caribbean were last updated today.
How many operators does momondo search for flights from Evansville Dress Regional Airport to Caribbean?
As of February 2026, there are 2 operators available to choose from for flights from Evansville Dress Regional Airport to Caribbean.
How old do you have to be to fly from Evansville Dress Regional Airport to Caribbean?
Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Evansville Dress Regional Airport to Caribbean.
What documentation or ID do you need to fly to Caribbean?
The required travel and health documents for your Caribbean trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Caribbean. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

Best airlines flying from Evansville to Caribbean

Compare and see reviews for airlines that fly from Evansville to Caribbean with momondo

Airline	Rating	Free Cancellation	Price
American Airlines	PriceFrom $285	Free Cancellation	Rating 7.2 11,288 reviews		Search American Airlines flights
Delta	PriceFrom $371	Free Cancellation	Rating 7.9 8,203 reviews		Search Delta flights

Why use momondo?

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

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Caribbean from Evansville.

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

Yes. All flights to Caribbean from Evansville on momondo can be compared and filtered by various policies on offer, including flexible booking.

How can momondo help me find flights from Evansville to Caribbean?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Evansville to Caribbean.

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

Of course. momondo tracks the price of Evansville to Caribbean flights. All you need is a valid email address and we will do the rest; it is that quick and easy.