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 49% of people opting to fly with this airline when traveling to Caribbean Islands. Keep in mind that there are 4 different airlines that fly to Caribbean Islands 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 Islands?

American Airlines is the most popular carrier operating from Evansville Dress Regional to Caribbean Islands

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 August 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.

$298 Cheap Flights from Evansville to Caribbean Islands in 2026

Discover deals from 900+ travel sites with momondo.

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.

5:59 pm - 3:07 pmEVV Evansville Dress Regional-SJU San Juan Luis Munoz Marin Intl

20h 08m2 stops Dallas/Fort Worth Charlotte Douglas

6:20 am - 4:12 pmSJU San Juan Luis Munoz Marin Intl-EVV Evansville Dress Regional

10h 52m2 stops Miami Charlotte Douglas

$366American Airlines

Sat, Oct 3 - Wed, Oct 7

12:25 pm - 9:24 amEVV Evansville Dress Regional-SJU San Juan Luis Munoz Marin Intl

19h 59m2 stops Dallas/Fort Worth Miami

12:41 pm - 9:23 pmSJU San Juan Luis Munoz Marin Intl-EVV Evansville Dress Regional

9h 42m1 stop Charlotte Douglas

$366American Airlines

Sat, Oct 3 - Wed, Oct 7

12:25 pm - 9:24 amEVV Evansville Dress Regional-SJU San Juan Luis Munoz Marin Intl

19h 59m2 stops Dallas/Fort Worth Miami

12:41 pm - 9:23 pmSJU San Juan Luis Munoz Marin Intl-EVV Evansville Dress Regional

9h 42m1 stop Charlotte Douglas

$366American Airlines

Sat, Oct 3 - Wed, Oct 7

5:59 pm - 3:07 pmEVV Evansville Dress Regional-SJU San Juan Luis Munoz Marin Intl

20h 08m2 stops Dallas/Fort Worth Charlotte Douglas

6:20 am - 4:12 pmSJU San Juan Luis Munoz Marin Intl-EVV Evansville Dress Regional

10h 52m2 stops Miami Charlotte Douglas

$366American Airlines

Sat, Oct 3 - Wed, Oct 7

6:16 am - 4:49 pmEVV Evansville Dress Regional-SJU San Juan Luis Munoz Marin Intl

9h 33m1 stop Atlanta Hartsfield-Jackson

2:59 pm - 10:07 pmSJU San Juan Luis Munoz Marin Intl-EVV Evansville Dress Regional

8h 08m1 stop Atlanta Hartsfield-Jackson

$440Delta

Sat, Oct 3 - Wed, Oct 7

6:16 am - 4:49 pmEVV Evansville Dress Regional-SJU San Juan Luis Munoz Marin Intl

9h 33m1 stop Atlanta Hartsfield-Jackson

2:59 pm - 10:07 pmSJU San Juan Luis Munoz Marin Intl-EVV Evansville Dress Regional

8h 08m1 stop Atlanta Hartsfield-Jackson

$440Delta

Sat, Oct 3 - Wed, Oct 7

6:16 am - 1:42 pmEVV Evansville Dress Regional-STT Saint Thomas Island Cyril E King

6h 26m1 stop Atlanta Hartsfield-Jackson

2:47 pm - 10:07 pmSTT Saint Thomas Island Cyril E King-EVV Evansville Dress Regional

8h 20m1 stop Atlanta Hartsfield-Jackson

$703Delta

Sat, Oct 3 - Tue, Oct 6

6:16 am - 1:27 pmEVV Evansville Dress Regional-SDQ Santo Domingo Las Americas

6h 11m1 stop Atlanta Hartsfield-Jackson

2:53 pm - 8:57 pmSDQ Santo Domingo Las Americas-EVV Evansville Dress Regional

7h 04m1 stop Atlanta Hartsfield-Jackson

$860Delta

Wed, Sep 9 - Thu, Sep 10

3:38 pm - 6:29 pmEVV Evansville Dress Regional-MBJ Montego Bay Sangster Intl

26h 51m2 stops Atlanta Hartsfield-Jackson Toronto Pearson Intl

1:50 pm - 11:07 pmMBJ Montego Bay Sangster Intl-EVV Evansville Dress Regional

33h 17m2 stops Calgary Atlanta Hartsfield-Jackson

$1,440WestJet

Sat, Oct 24 - Sat, Oct 31

10:04 am - 11:45 amEVV Evansville Dress Regional-MBJ Montego Bay Sangster Intl

49h 41m2 stops Atlanta Hartsfield-Jackson Toronto Pearson Intl

12:45 pm - 2:21 pmMBJ Montego Bay Sangster Intl-EVV Evansville Dress Regional

25h 36m2 stops Toronto Pearson Intl Atlanta Hartsfield-Jackson

$4,171WestJet

Tue, Sep 1 - Fri, Sep 4

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American Airlines flights from Evansville to Caribbean Islands

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

American Airlines

Oct 12

EVV4:38 pmEvansville Dress Regional

19h 50m

2 stops

SJU1:28 pmSan Juan Luis Munoz Marin Intl

Oct 16

SJU12:41 pmSan Juan Luis Munoz Marin Intl

9h 42m

1 stop

EVV9:23 pmEvansville Dress Regional

$406

American Airlines

Jan 12

EVV6:51 amEvansville Dress Regional

9h 19m

1 stop

MBJ5:10 pmMontego Bay Sangster Intl

Feb 9

MBJ1:16 pmMontego Bay Sangster Intl

11h 06m

1 stop

EVV11:22 pmEvansville Dress Regional

$413

American Airlines

Jan 12

EVV6:51 amEvansville Dress Regional

9h 19m

1 stop

MBJ5:10 pmMontego Bay Sangster Intl

Feb 9

MBJ4:16 pmMontego Bay Sangster Intl

20h 33m

2 stops

EVV11:49 amEvansville Dress Regional

$418

Delta flights from Evansville to Caribbean Islands

Our best Delta deals on Evansville to Caribbean Islands flight tickets

Delta

Sep 24

EVV1:43 pmEvansville Dress Regional

7h 36m

1 stop

SJU10:19 pmSan Juan Luis Munoz Marin Intl

Sep 29

SJU7:00 amSan Juan Luis Munoz Marin Intl

7h 03m

1 stop

EVV1:03 pmEvansville Dress Regional

$514

Delta

Sep 16

EVV6:16 amEvansville Dress Regional

9h 33m

1 stop

SJU4:49 pmSan Juan Luis Munoz Marin Intl

Sep 19

SJU12:56 pmSan Juan Luis Munoz Marin Intl

9h 01m

1 stop

EVV8:57 pmEvansville Dress Regional

$622

Delta

Oct 3

EVV6:16 amEvansville Dress Regional

6h 26m

1 stop

STT1:42 pmSaint Thomas Island Cyril E King

Oct 6

STT2:47 pmSaint Thomas Island Cyril E King

8h 20m

1 stop

EVV10:07 pmEvansville Dress Regional

$703

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

Cheapest round-trip

EvansvilleSan Juan

EVV Evansville Dress Regional - SJU San Juan Luis Munoz Marin Intl

EVVSJU

Evansville Dress Regional

Sat 10/3

5:59 pm-3:07 pm

2 stops20h 08m

San Juan Luis Munoz Marin Intl

Wed 10/7

6:20 am-4:12 pm

2 stops10h 52m

$366

EvansvilleSan Juan

EVV Evansville Dress Regional - SJU San Juan Luis Munoz Marin Intl

EVVSJU

Evansville Dress Regional

Sat 10/3

12:25 pm-9:24 am

2 stops19h 59m

San Juan Luis Munoz Marin Intl

Wed 10/7

12:41 pm-9:23 pm

1 stop9h 42m

$366

EvansvilleSan Juan

EVV Evansville Dress Regional - SJU San Juan Luis Munoz Marin Intl

EVVSJU

Evansville Dress Regional

Sat 10/3

12:25 pm-9:24 am

2 stops19h 59m

San Juan Luis Munoz Marin Intl

Wed 10/7

12:41 pm-9:23 pm

1 stop9h 42m

$366

EvansvilleSan Juan

EVV Evansville Dress Regional - SJU San Juan Luis Munoz Marin Intl

EVVSJU

Evansville Dress Regional

Sat 10/3

5:59 pm-3:07 pm

2 stops20h 08m

San Juan Luis Munoz Marin Intl

Wed 10/7

6:20 am-4:12 pm

2 stops10h 52m

$366

EvansvilleSan Juan

EVV Evansville Dress Regional - SJU San Juan Luis Munoz Marin Intl

EVVSJU

Evansville Dress Regional

Sat 10/3

6:16 am-4:49 pm

1 stop9h 33m

San Juan Luis Munoz Marin Intl

Wed 10/7

2:59 pm-10:07 pm

1 stop8h 08m

$440

EvansvilleSan Juan

EVV Evansville Dress Regional - SJU San Juan Luis Munoz Marin Intl

EVVSJU

Evansville Dress Regional

Sat 10/3

6:16 am-4:49 pm

1 stop9h 33m

San Juan Luis Munoz Marin Intl

Wed 10/7

2:59 pm-10:07 pm

1 stop8h 08m

$440

EvansvilleSaint Thomas Island

EVV Evansville Dress Regional - STT Saint Thomas Island Cyril E King

EVVSTT

Evansville Dress Regional

Sat 10/3

6:16 am-1:42 pm

1 stop6h 26m

Saint Thomas Island Cyril E King

Tue 10/6

2:47 pm-10:07 pm

1 stop8h 20m

$703

Quickest round-trip

EvansvilleSanto Domingo

EVV Evansville Dress Regional - SDQ Santo Domingo Las Americas

EVVSDQ

Evansville Dress Regional

Wed 9/9

6:16 am-1:27 pm

1 stop6h 11m

Santo Domingo Las Americas

Thu 9/10

2:53 pm-8:57 pm

1 stop7h 04m

$860

EvansvilleMontego Bay

EVV Evansville Dress Regional - MBJ Montego Bay Sangster Intl

EVVMBJ

Evansville Dress Regional

Sat 10/24

3:38 pm-6:29 pm

2 stops26h 51m

Montego Bay Sangster Intl

Sat 10/31

1:50 pm-11:07 pm

2 stops33h 17m

$1,440

EvansvilleMontego Bay

EVV Evansville Dress Regional - MBJ Montego Bay Sangster Intl

EVVMBJ

Evansville Dress Regional

Tue 9/1

10:04 am-11:45 am

2 stops49h 41m

Montego Bay Sangster Intl

Fri 9/4

12:45 pm-2:21 pm

2 stops25h 36m

$4,171

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 15 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

Best Price Found	$298
Fastest flight time	5h 49m
Direct flights	None

The best one-way flight to Caribbean Islands from Evansville in the past 72 hours is $298. The best round-trip flight deal from Evansville to Caribbean Islands found on momondo in the last 72 hours is $366.

The fastest flight from Evansville to Caribbean Islands takes 5h 49m

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

Search flight deals

Frequently asked questions about flying from Evansville to Caribbean Islands

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 August 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 Airbus A320-100/200, making up 25.93% of the total bookings. Other popular models include Boeing 737 MAX 8 with 13.99%, Airbus A220-300 with 12.35%, and Embraer 175 with 8.23%.

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 7.1 11,961 reviews		Search American Airlines flights
Delta	PriceFrom $336	Free Cancellation	Rating 7.8 8,499 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.