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

American Airlines and Delta 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 52% 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.

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 July 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.

$326 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.

4:53 pm - 2:50 pm

EVV

SJU

20h 57m

2 stops

6:27 am - 11:29 pm

SJU

EVV

18h 02m

2 stops

$326American Airlines

Mon, Sep 21 - Mon, Sep 28

6:16 am - 1:47 pm

EVV

SJU

6h 31m

1 stop

12:56 pm - 9:49 pm

SJU

EVV

9h 53m

1 stop

$410Delta

Mon, Sep 21 - Mon, Sep 28

5:45 pm - 3:40 pm

EVV

SJU

20h 55m

2 stops

3:35 pm - 11:29 pm

SJU

EVV

8h 54m

1 stop

$446American Airlines

Mon, Sep 21 - Mon, Sep 28

6:05 pm - 1:34 pm

EVV

MBJ

19h 29m

2 stops

5:08 pm - 11:50 am

MBJ

EVV

18h 42m

2 stops

$452American Airlines

Sat, Aug 15 - Sat, Aug 22

4:29 pm - 7:57 am

EVV

SJU

14h 28m

1 stop

3:10 am - 3:49 pm

SJU

EVV

13h 39m

1 stop

$457Multiple Airlines

Sat, Aug 1 - Fri, Aug 7

5:59 pm - 4:16 pm

EVV

MBJ

22h 17m

1 stop

5:13 pm - 4:12 pm

MBJ

EVV

22h 59m

2 stops

$459American Airlines

Sat, Oct 3 - Sat, Oct 10

4:29 pm - 7:57 am

EVV

SJU

14h 28m

1 stop

3:36 pm - 3:49 pm

SJU

EVV

25h 13m

2 stops

$474Multiple Airlines

Wed, Jul 15 - Tue, Jul 21

4:29 pm - 2:15 am

EVV

SJU

8h 46m

1 stop

3:36 pm - 7:48 pm

SJU

EVV

29h 12m

2 stops

$475Multiple Airlines

Sat, Aug 1 - Sat, Aug 8

5:59 pm - 1:35 pm

EVV

PUJ

18h 36m

2 stops

2:35 pm - 5:19 pm

PUJ

EVV

27h 44m

2 stops

$3,430WestJet

Mon, Jul 13 - Tue, Jul 21

3:38 pm - 2:35 pm

EVV

PUJ

45h 57m

2 stops

3:30 pm - 5:19 pm

PUJ

EVV

26h 49m

2 stops

$3,745WestJet

Sat, Oct 24 - Wed, Oct 28

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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

Sep 21

EVV4:53 pmEvansville Dress Regional

20h 57m

2 stops

SJU2:50 pmSan Juan Luis Munoz Marin Intl

Sep 28

SJU6:27 amSan Juan Luis Munoz Marin Intl

18h 02m

2 stops

EVV11:29 pmEvansville Dress Regional

$326

American Airlines

Sep 21

EVV5:45 pmEvansville Dress Regional

20h 55m

2 stops

SJU3:40 pmSan Juan Luis Munoz Marin Intl

Sep 28

SJU3:35 pmSan Juan Luis Munoz Marin Intl

8h 54m

1 stop

EVV11:29 pmEvansville Dress Regional

$446

American Airlines

Aug 15

EVV6:05 pmEvansville Dress Regional

19h 29m

2 stops

MBJ1:34 pmMontego Bay Sangster Intl

Aug 22

MBJ5:08 pmMontego Bay Sangster Intl

18h 42m

2 stops

EVV11:50 amEvansville Dress Regional

$452

Delta flights from Evansville to Caribbean Islands

Our best Delta deals on Evansville to Caribbean Islands flight tickets

Delta

Sep 21

EVV6:16 amEvansville Dress Regional

6h 31m

1 stop

SJU1:47 pmSan Juan Luis Munoz Marin Intl

Sep 28

SJU12:56 pmSan Juan Luis Munoz Marin Intl

9h 53m

1 stop

EVV9:49 pmEvansville Dress Regional

$410

Delta

Aug 15

EVV6:25 amEvansville Dress Regional

9h 09m

1 stop

MBJ3:34 pmMontego Bay Sangster Intl

Aug 22

MBJ1:09 pmMontego Bay Sangster Intl

7h 39m

1 stop

EVV8:48 pmEvansville Dress Regional

$512

Delta

Jul 12

EVV1:42 pmEvansville Dress Regional

7h 47m

1 stop

SJU10:29 pmSan Juan Luis Munoz Marin Intl

Jul 21

SJU6:00 amSan Juan Luis Munoz Marin Intl

8h 02m

1 stop

EVV1:02 pmEvansville Dress Regional

$583

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 - SJU

EVVSJU

Evansville Dress Regional

Mon 9/21

4:53 pm-2:50 pm

2 stops20h 57m

San Juan Luis Munoz Marin Intl

Mon 9/28

6:27 am-11:29 pm

2 stops18h 02m

$326

Quickest round-trip

EvansvilleSan Juan

EVV - SJU

EVVSJU

Evansville Dress Regional

Mon 9/21

6:16 am-1:47 pm

1 stop6h 31m

San Juan Luis Munoz Marin Intl

Mon 9/28

12:56 pm-9:49 pm

1 stop9h 53m

$410

EvansvilleSan Juan

EVV - SJU

EVVSJU

Evansville Dress Regional

Mon 9/21

5:45 pm-3:40 pm

2 stops20h 55m

San Juan Luis Munoz Marin Intl

Mon 9/28

3:35 pm-11:29 pm

1 stop8h 54m

$446

EvansvilleMontego Bay

EVV - MBJ

EVVMBJ

Evansville Dress Regional

Sat 8/15

6:05 pm-1:34 pm

2 stops19h 29m

Montego Bay Sangster Intl

Sat 8/22

5:08 pm-11:50 am

2 stops18h 42m

$452

EvansvilleSan Juan

EVV - SJU

EVVSJU

Evansville Dress Regional

Sat 8/1

4:29 pm-7:57 am

1 stop14h 28m

San Juan Luis Munoz Marin Intl

Fri 8/7

3:10 am-3:49 pm

1 stop13h 39m

$457

EvansvilleMontego Bay

EVV - MBJ

EVVMBJ

Evansville Dress Regional

Sat 10/3

5:59 pm-4:16 pm

1 stop22h 17m

Montego Bay Sangster Intl

Sat 10/10

5:13 pm-4:12 pm

2 stops22h 59m

$459

EvansvilleSan Juan

EVV - SJU

EVVSJU

Evansville Dress Regional

Wed 7/15

4:29 pm-7:57 am

1 stop14h 28m

San Juan Luis Munoz Marin Intl

Tue 7/21

3:36 pm-3:49 pm

2 stops25h 13m

$474

EvansvilleSan Juan

EVV - SJU

EVVSJU

Evansville Dress Regional

Sat 8/1

4:29 pm-2:15 am

1 stop8h 46m

San Juan Luis Munoz Marin Intl

Sat 8/8

3:36 pm-7:48 pm

2 stops29h 12m

$475

EvansvillePunta Cana

EVV - PUJ

EVVPUJ

Evansville Dress Regional

Mon 7/13

5:59 pm-1:35 pm

2 stops18h 36m

Punta Cana

Tue 7/21

2:35 pm-5:19 pm

2 stops27h 44m

$3,430

EvansvillePunta Cana

EVV - PUJ

EVVPUJ

Evansville Dress Regional

Sat 10/24

3:38 pm-2:35 pm

2 stops45h 57m

Punta Cana

Wed 10/28

3:30 pm-5:19 pm

2 stops26h 49m

$3,745

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 13 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

What is the cheapest month to fly to Caribbean Islands?

The month of November is, on average, the cheapest month to fly to Caribbean Islands from Evansville, with most prices found around $0. The month of August is another great option to travel to Caribbean Islands, with average flight prices from Evansville averaging around $388.

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	6h 03m
Direct flights	None

The fastest flight from Evansville to Caribbean Islands takes 6h 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

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 July 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 23.08% of the total bookings. Other popular models include Boeing 737 MAX 8 with 17.65%, Airbus A220-300 with 11.76%, and Canadair (Bombardier) Regional Jet 900 with 10.86%.

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 11,770 reviews		Search American Airlines flights
Delta	PriceFrom $336	Free Cancellation	Rating 7.8 8,452 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.