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 56% 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.

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 December 2025, 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.

$235 Cheap Flights from Evansville to Caribbean in 2025/26

1 adult

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Find the cheapest flights from Evansville to Caribbean

Round-trip

Last minute

Cheap round-trip flights

Enter your travel dates to find the best prices.

7:10 am - 9:39 pm

EVV

SJU

12h 29m1 stop

6:00 am - 8:58 pm

SJU

EVV

16h 58m1 stop

$235American Airlines

Fri, Jan 23 - Fri, Jan 30

11:57 am - 7:39 pm

EVV

SJU

6h 42m1 stop

4:25 pm - 11:47 pm

SJU

EVV

8h 22m1 stop

$298American Airlines

Tue, Mar 17 - Tue, Mar 24

7:10 am - 9:39 pm

EVV

SJU

12h 29m1 stop

6:00 am - 4:18 pm

SJU

EVV

12h 18m1 stop

$304American Airlines

Sat, Jan 17 - Mon, Jan 26

7:10 am - 9:39 pm

EVV

SJU

12h 29m1 stop

6:00 am - 4:18 pm

SJU

EVV

12h 18m1 stop

$305American Airlines

Sat, Jan 17 - Thu, Jan 22

6:13 am - 11:56 pm

EVV

SJU

15h 43m2 stops

6:00 am - 4:18 pm

SJU

EVV

12h 18m1 stop

$332American Airlines

Sat, Jan 17 - Sun, Jan 25

7:10 am - 9:39 pm

EVV

SJU

12h 29m1 stop

8:20 am - 8:58 pm

SJU

EVV

14h 38m2 stops

$368American Airlines

Sat, Jan 17 - Sun, Jan 25

7:10 am - 9:39 pm

EVV

SJU

12h 29m1 stop

8:20 am - 8:58 pm

SJU

EVV

14h 38m2 stops

$370American Airlines

Sat, Jan 17 - Sun, Jan 25

6:13 am - 11:56 pm

EVV

SJU

15h 43m2 stops

8:20 am - 8:58 pm

SJU

EVV

14h 38m2 stops

$397American Airlines

Sat, Jan 17 - Mon, Jan 26

6:15 am - 6:25 am

EVV

PUJ

22h 10m2 stops

4:30 pm - 10:22 pm

PUJ

EVV

31h 52m2 stops

$3,505WestJet

Sun, Jan 25 - Thu, Jan 29

11:40 am - 7:17 pm

EVV

MBJ

30h 37m2 stops

2:55 pm - 11:48 am

MBJ

EVV

21h 53m2 stops

$3,549WestJet

Mon, Feb 2 - Fri, Feb 6

American Airlines flights from Evansville to Caribbean

Our best American Airlines deals on Evansville to Caribbean flight tickets

American Airlines

Jan 23

EVV7:10 amEvansville Dress Regional

12h 29m

1 stop

SJU9:39 pmSan Juan Luis Munoz Marin Intl

Jan 30

SJU6:00 amSan Juan Luis Munoz Marin Intl

16h 58m

1 stop

EVV8:58 pmEvansville Dress Regional

$235

Find similar

American Airlines

Mar 17

EVV11:01 amEvansville Dress Regional

10h 30m

1 stop

SJU10:31 pmSan Juan Luis Munoz Marin Intl

Mar 24

SJU4:25 pmSan Juan Luis Munoz Marin Intl

8h 22m

1 stop

EVV11:47 pmEvansville Dress Regional

$298

Find similar

American Airlines

Jan 17

EVV7:10 amEvansville Dress Regional

12h 29m

1 stop

SJU9:39 pmSan Juan Luis Munoz Marin Intl

Jan 26

SJU6:00 amSan Juan Luis Munoz Marin Intl

12h 18m

1 stop

EVV4:18 pmEvansville Dress Regional

$304

Find similar

Delta flights from Evansville to Caribbean

Our best Delta deals on Evansville to Caribbean flight tickets

Delta

Dec 30

EVV6:07 amEvansville Dress Regional

9h 23m

1 stop

SJU5:30 pmSan Juan Luis Munoz Marin Intl

Jan 1

SJU6:30 amSan Juan Luis Munoz Marin Intl

11h 16m

1 stop

EVV3:46 pmEvansville Dress Regional

$787

Find similar

Delta

Dec 27

EVV6:07 amEvansville Dress Regional

6h 06m

1 stop

PUJ2:13 pmPunta Cana

Jan 1

PUJ2:06 pmPunta Cana

8h 41m

1 stop

EVV8:47 pmEvansville Dress Regional

$864

Find similar

Delta

Mar 27

EVV6:00 amEvansville Dress Regional

7h 43m

1 stop

STT2:43 pmSaint Thomas Island Cyril E King

Apr 5

STT3:00 pmSaint Thomas Island Cyril E King

8h 23m

1 stop

EVV10:23 pmEvansville Dress Regional

$1,506

Find similar

Fly from

Fly to

Route

Depart

Return

Price

EvansvilleSan Juan

EVV - SJU

EVVSJU

Evansville Dress Regional

Fri 1/23

7:10 am-9:39 pm

1 stop12h 29m

San Juan Luis Munoz Marin Intl

Fri 1/30

6:00 am-8:58 pm

1 stop16h 58m

$235

EvansvilleSan Juan

EVV - SJU

EVVSJU

Evansville Dress Regional

Tue 3/17

11:57 am-7:39 pm

1 stop6h 42m

San Juan Luis Munoz Marin Intl

Tue 3/24

4:25 pm-11:47 pm

1 stop8h 22m

$298

EvansvilleSan Juan

EVV - SJU

EVVSJU

Evansville Dress Regional

Sat 1/17

7:10 am-9:39 pm

1 stop12h 29m

San Juan Luis Munoz Marin Intl

Mon 1/26

6:00 am-4:18 pm

1 stop12h 18m

$304

EvansvilleSan Juan

EVV - SJU

EVVSJU

Evansville Dress Regional

Sat 1/17

7:10 am-9:39 pm

1 stop12h 29m

San Juan Luis Munoz Marin Intl

Thu 1/22

6:00 am-4:18 pm

1 stop12h 18m

$305

EvansvilleSan Juan

EVV - SJU

EVVSJU

Evansville Dress Regional

Sat 1/17

6:13 am-11:56 pm

2 stops15h 43m

San Juan Luis Munoz Marin Intl

Sun 1/25

6:00 am-4:18 pm

1 stop12h 18m

$332

EvansvilleSan Juan

EVV - SJU

EVVSJU

Evansville Dress Regional

Sat 1/17

7:10 am-9:39 pm

1 stop12h 29m

San Juan Luis Munoz Marin Intl

Sun 1/25

8:20 am-8:58 pm

2 stops14h 38m

$368

EvansvilleSan Juan

EVV - SJU

EVVSJU

Evansville Dress Regional

Sat 1/17

7:10 am-9:39 pm

1 stop12h 29m

San Juan Luis Munoz Marin Intl

Sun 1/25

8:20 am-8:58 pm

2 stops14h 38m

$370

EvansvilleSan Juan

EVV - SJU

EVVSJU

Evansville Dress Regional

Sat 1/17

6:13 am-11:56 pm

2 stops15h 43m

San Juan Luis Munoz Marin Intl

Mon 1/26

8:20 am-8:58 pm

2 stops14h 38m

$397

EvansvillePunta Cana

EVV - PUJ

EVVPUJ

Evansville Dress Regional

Sun 1/25

6:15 am-6:25 am

2 stops22h 10m

Punta Cana

Thu 1/29

4:30 pm-10:22 pm

2 stops31h 52m

$3,505

EvansvilleMontego Bay

EVV - MBJ

EVVMBJ

Evansville Dress Regional

Mon 2/2

11:40 am-7:17 pm

2 stops30h 37m

Montego Bay Sangster Intl

Fri 2/6

2:55 pm-11:48 am

2 stops21h 53m

$3,549

Flights are sorted by cheapest round-trip flights first.

Sorted 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

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

The cheapest day to depart from Evansville to Caribbean is on a Saturday when prices can be found for as low as $407. If your travel schedule is flexible, try to avoid departing on a Thursday because tickets tend to average around $664. These prices are subject to change though, so be sure to set up a Price Alert for flights to Caribbean.

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

At noon is the cheapest time of day to fly from Evansville to Caribbean when you can find flight prices for as low as $394. Flying to Caribbean at noon is an ideal time because this is during off-peak travel hours. Flights in the afternoon are often more expensive with an average ticket price of $604.

Can stopping save me money on Evansville to Caribbean flights?

You could potentially save up to 3% 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	5h 39m
Direct flights	None

The fastest flight from Evansville to Caribbean takes 5h 39m

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 December 2025, 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 $275	Free Cancellation	Rating 7.2 11,062 reviews		Search American Airlines flights
Delta	PriceFrom $371	Free Cancellation	Rating 7.9 8,013 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.