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

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

What airlines fly to Caribbean Islands?

American Airlines, Delta and Southwest are the top three most popular airlines that fly to Caribbean Islands 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 Islands. Keep in mind that there are 5 different airlines that fly to Caribbean Islands 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 Islands?

Prices for flights from Evansville Dress Regional Airport to Caribbean Islands are refreshed on a daily basis.

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

The number of operators available for flights from Evansville Dress Regional Airport to Caribbean Islands is 2 as of February 2026.

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

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

The necessary travel and health documents for your Caribbean Islands trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

$212 Cheap Flights from Evansville to Caribbean Islands in 2026

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Find the cheapest flights from Evansville to Caribbean Islands

Round-trip

One-way

Last minute

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

6:01 pm - 10:56 am

EVV

SJU

15h 55m

2 stops

5:28 am - 3:49 pm

SJU

EVV

11h 21m

1 stop

$306American Airlines

Tue, Mar 17 - Tue, Mar 24

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

7:46 pm - 9:54 am

EVV

SJU

12h 08m

1 stop

6:00 am - 7:06 pm

SJU

EVV

15h 06m

1 stop

$336Multiple Airlines

Mon, Feb 23 - Fri, Feb 27

7:46 pm - 3:31 pm

EVV

SJU

17h 45m

2 stops

6:00 am - 7:06 pm

SJU

EVV

15h 06m

1 stop

$343Multiple Airlines

Mon, Feb 23 - Fri, Feb 27

5:30 pm - 4:35 am

EVV

SJU

10h 05m

1 stop

12:59 am - 12:21 pm

SJU

EVV

12h 22m

2 stops

$345American Airlines

Sun, May 24 - Fri, May 29

6:05 am - 7:39 pm

EVV

SJU

12h 34m

1 stop

5:28 am - 3:49 pm

SJU

EVV

11h 21m

1 stop

$346American Airlines

Tue, Mar 17 - Tue, Mar 24

6:18 am - 3:21 pm

EVV

STT

8h 03m

1 stop

1:20 pm - 9:44 pm

STT

EVV

9h 24m

1 stop

$708Delta

Wed, May 20 - Wed, May 27

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

11:14 am - 1:49 pm

EVV

MBJ

49h 35m

2 stops

2:55 pm - 5:14 pm

MBJ

EVV

27h 19m

2 stops

$4,560WestJet

Mon, Feb 23 - Thu, Feb 26

American Airlines flights from Evansville to Caribbean Islands

Our best American Airlines deals on Evansville to Caribbean Islands flight tickets

American Airlines

May 4

EVV6:56 pmEvansville Dress Regional

16h 33m

2 stops

SJU12:29 pmSan Juan Luis Munoz Marin Intl

May 19

SJU7:25 amSan Juan Luis Munoz Marin Intl

16h 33m

1 stop

EVV10:58 pmEvansville Dress Regional

$299

American Airlines

Mar 17

EVV6:01 pmEvansville Dress Regional

15h 55m

2 stops

SJU10:56 amSan Juan Luis Munoz Marin Intl

Mar 24

SJU5:28 amSan Juan Luis Munoz Marin Intl

11h 21m

1 stop

EVV3:49 pmEvansville Dress Regional

$306

American Airlines

May 24

EVV5:30 pmEvansville Dress Regional

10h 05m

1 stop

SJU4:35 amSan Juan Luis Munoz Marin Intl

May 29

SJU12:59 amSan Juan Luis Munoz Marin Intl

18h 02m

1 stop

EVV6:01 pmEvansville Dress Regional

$345

Delta flights from Evansville to Caribbean Islands

Our best Delta deals on Evansville to Caribbean Islands flight tickets

Delta

May 20

EVV6:18 amEvansville Dress Regional

8h 03m

1 stop

STT3:21 pmSaint Thomas Island Cyril E King

May 27

STT1:20 pmSaint Thomas Island Cyril E King

9h 24m

1 stop

EVV9:44 pmEvansville Dress Regional

$708

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

EVV11:14 amEvansville Dress Regional

10h 44m

1 stop

SJU11:58 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

momondo Fare Finder

Use the filters below to find and compare flights from Evansville to Caribbean Islands that are best for you.

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

Tue 3/17

6:01 pm-10:56 am

2 stops15h 55m

San Juan Luis Munoz Marin Intl

Tue 3/24

5:28 am-3:49 pm

1 stop11h 21m

$306

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

Mon 2/23

7:46 pm-9:54 am

1 stop12h 08m

San Juan Luis Munoz Marin Intl

Fri 2/27

6:00 am-7:06 pm

1 stop15h 06m

$336

EvansvilleSan Juan

EVV - SJU

EVVSJU

Evansville Dress Regional

Mon 2/23

7:46 pm-3:31 pm

2 stops17h 45m

San Juan Luis Munoz Marin Intl

Fri 2/27

6:00 am-7:06 pm

1 stop15h 06m

$343

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-12:21 pm

2 stops12h 22m

$345

EvansvilleSan Juan

EVV - SJU

EVVSJU

Evansville Dress Regional

Tue 3/17

6:05 am-7:39 pm

1 stop12h 34m

San Juan Luis Munoz Marin Intl

Tue 3/24

5:28 am-3:49 pm

1 stop11h 21m

$346

EvansvilleSaint Thomas Island

EVV - STT

EVVSTT

Evansville Dress Regional

Wed 5/20

6:18 am-3:21 pm

1 stop8h 03m

Saint Thomas Island Cyril E King

Wed 5/27

1:20 pm-9:44 pm

1 stop9h 24m

$708

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

EvansvilleMontego Bay

EVV - MBJ

EVVMBJ

Evansville Dress Regional

Mon 2/23

11:14 am-1:49 pm

2 stops49h 35m

Montego Bay Sangster Intl

Thu 2/26

2:55 pm-5:14 pm

2 stops27h 19m

$4,560

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 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

Prices

Airlines

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

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

Cheap Evansville to Caribbean Islands flight deals and tips

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

Fastest flight time	8h 03m
Direct flights	None

The fastest flight from Evansville to Caribbean Islands takes 8h 03m

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

Search flight deals

When did momondo last update prices for flights from Evansville Dress Regional Airport to Caribbean Islands?
Prices for flights from Evansville Dress Regional Airport to Caribbean Islands are refreshed on a daily basis.
How many operators does momondo search for flights from Evansville Dress Regional Airport to Caribbean Islands?
The number of operators available for flights from Evansville Dress Regional Airport to Caribbean Islands is 2 as of February 2026.
How old do you have to be to fly from Evansville Dress Regional Airport 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 Evansville Dress Regional Airport to Caribbean Islands.
What documentation or ID do you need to fly to Caribbean Islands?
The necessary travel and health documents for your Caribbean Islands trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Evansville to Caribbean Islands?
Based on momondo bookings for flights between Evansville and Caribbean Islands, the leading plane model is Boeing 737 MAX 8, making up 27.27% of the total bookings. Other popular models include Airbus A220-300 with 20.78%, Airbus A319 with 13.85%, and Canadair (Bombardier) Regional Jet 900 with 6.93%.

Best airlines flying from Evansville to Caribbean Islands

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

Airline	Rating	Free Cancellation	Price
American Airlines	PriceFrom $285	Free Cancellation	Rating 7.2 11,278 reviews		Search American Airlines flights
Delta	PriceFrom $371	Free Cancellation	Rating 7.9 8,193 reviews		Search Delta flights

Why use momondo?

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

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Evansville to Caribbean Islands for you.

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

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

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

Once you have performed a search for Evansville to Caribbean Islands flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

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

Yes momondo offers price alerts on flights to Caribbean Islands from Evansville. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.