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 50% 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 May 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.

$371 Cheap Flights from Evansville to Caribbean Islands in 2026

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Find the cheapest flights from Evansville to Caribbean Islands

Round-trip

Last minute

Cheap round-trip flights

Enter your travel dates to find the best prices.

5:14 pm - 1:09 pm

EVV

MBJ

19h 55m

2 stops

2:09 pm - 12:20 pm

MBJ

EVV

22h 11m

2 stops

$371American Airlines

Fri, Jul 3 - Tue, Jul 7

7:29 am - 12:50 pm

EVV

STT

28h 21m

2 stops

1:50 pm - 12:06 pm

STT

EVV

23h 16m

2 stops

$420American Airlines

Fri, Sep 18 - Wed, Sep 23

6:22 am - 11:59 am

EVV

MBJ

5h 37m

1 stop

12:59 pm - 5:19 pm

MBJ

EVV

28h 20m

2 stops

$427Delta

Fri, Jul 3 - Wed, Jul 8

5:14 pm - 11:47 am

EVV

MBJ

18h 33m

2 stops

12:47 pm - 11:31 pm

MBJ

EVV

10h 44m

1 stop

$439American Airlines

Fri, Jul 3 - Tue, Jul 7

6:04 pm - 12:50 pm

EVV

STT

17h 46m

2 stops

1:50 pm - 9:54 am

STT

EVV

21h 04m

2 stops

$485American Airlines

Mon, Sep 28 - Sun, Oct 4

4:36 pm - 10:40 am

EVV

STT

17h 04m

1 stop

4:18 pm - 10:36 am

STT

EVV

20h 18m

2 stops

$490American Airlines

Wed, Oct 28 - Wed, Nov 4

4:34 pm - 11:02 am

EVV

SJU

17h 28m

2 stops

12:57 am - 6:05 pm

SJU

EVV

18h 08m

1 stop

$499American Airlines

Sat, Jun 13 - Thu, Jun 18

6:00 am - 1:39 pm

EVV

STT

6h 39m

1 stop

3:49 pm - 10:03 pm

STT

EVV

8h 14m

1 stop

$520Delta

Wed, Oct 28 - Wed, Nov 4

10:18 am - 3:34 pm

EVV

MBJ

5h 16m

1 stop

4:59 pm - 9:26 am

MBJ

EVV

16h 27m

1 stop

$525Delta

Sat, Jul 4 - Thu, Jul 9

8:16 pm - 8:25 pm

EVV

PUJ

23h 09m

1 stop

3:44 pm - 3:49 pm

PUJ

EVV

25h 05m

2 stops

$724Multiple Airlines

Thu, Jul 23 - Fri, Jul 31

American Airlines flights from Evansville to Caribbean Islands

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

American Airlines

Jul 3

EVV5:14 pmEvansville Dress Regional

19h 55m

2 stops

MBJ1:09 pmMontego Bay Sangster Intl

Jul 7

MBJ2:09 pmMontego Bay Sangster Intl

22h 11m

2 stops

EVV12:20 pmEvansville Dress Regional

$371

American Airlines

Sep 18

EVV7:29 amEvansville Dress Regional

28h 21m

2 stops

STT12:50 pmSaint Thomas Island Cyril E King

Sep 23

STT1:50 pmSaint Thomas Island Cyril E King

23h 16m

2 stops

EVV12:06 pmEvansville Dress Regional

$420

American Airlines

Jul 3

EVV5:14 pmEvansville Dress Regional

18h 33m

2 stops

MBJ11:47 amMontego Bay Sangster Intl

Jul 7

MBJ12:47 pmMontego Bay Sangster Intl

10h 44m

1 stop

EVV11:31 pmEvansville Dress Regional

$439

WestJet flights from Evansville to Caribbean Islands

Our best WestJet deals on Evansville to Caribbean Islands flight tickets

WestJet

Jul 26

EVV5:59 pmEvansville Dress Regional

42h 36m

2 stops

PUJ1:35 pmPunta Cana

Jul 30

PUJ3:00 pmPunta Cana

19h 26m

2 stops

EVV9:26 amEvansville Dress Regional

$3,507

WestJet

Sep 1

EVV5:45 pmEvansville Dress Regional

42h 00m

2 stops

MBJ11:45 amMontego Bay Sangster Intl

Sep 5

MBJ7:30 pmMontego Bay Sangster Intl

26h 33m

2 stops

EVV10:03 pmEvansville Dress Regional

$3,684

WestJet

Sep 1

EVV1:30 pmEvansville Dress Regional

22h 15m

2 stops

MBJ11:45 amMontego Bay Sangster Intl

Sep 5

MBJ7:30 pmMontego Bay Sangster Intl

26h 33m

2 stops

EVV10:03 pmEvansville Dress Regional

$3,686

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

EvansvilleMontego Bay

EVV - MBJ

EVVMBJ

Evansville Dress Regional

Fri 7/3

5:14 pm-1:09 pm

2 stops19h 55m

Montego Bay Sangster Intl

Tue 7/7

2:09 pm-12:20 pm

2 stops22h 11m

$371

EvansvilleSaint Thomas Island

EVV - STT

EVVSTT

Evansville Dress Regional

Fri 9/18

7:29 am-12:50 pm

2 stops28h 21m

Saint Thomas Island Cyril E King

Wed 9/23

1:50 pm-12:06 pm

2 stops23h 16m

$420

EvansvilleMontego Bay

EVV - MBJ

EVVMBJ

Evansville Dress Regional

Fri 7/3

6:22 am-11:59 am

1 stop5h 37m

Montego Bay Sangster Intl

Wed 7/8

12:59 pm-5:19 pm

2 stops28h 20m

$427

EvansvilleMontego Bay

EVV - MBJ

EVVMBJ

Evansville Dress Regional

Fri 7/3

5:14 pm-11:47 am

2 stops18h 33m

Montego Bay Sangster Intl

Tue 7/7

12:47 pm-11:31 pm

1 stop10h 44m

$439

EvansvilleSaint Thomas Island

EVV - STT

EVVSTT

Evansville Dress Regional

Mon 9/28

6:04 pm-12:50 pm

2 stops17h 46m

Saint Thomas Island Cyril E King

Sun 10/4

1:50 pm-9:54 am

2 stops21h 04m

$485

EvansvilleSaint Thomas Island

EVV - STT

EVVSTT

Evansville Dress Regional

Wed 10/28

4:36 pm-10:40 am

1 stop17h 04m

Saint Thomas Island Cyril E King

Wed 11/4

4:18 pm-10:36 am

2 stops20h 18m

$490

EvansvilleSan Juan

EVV - SJU

EVVSJU

Evansville Dress Regional

Sat 6/13

4:34 pm-11:02 am

2 stops17h 28m

San Juan Luis Munoz Marin Intl

Thu 6/18

12:57 am-6:05 pm

1 stop18h 08m

$499

Quickest round-trip

EvansvilleSaint Thomas Island

EVV - STT

EVVSTT

Evansville Dress Regional

Wed 10/28

6:00 am-1:39 pm

1 stop6h 39m

Saint Thomas Island Cyril E King

Wed 11/4

3:49 pm-10:03 pm

1 stop8h 14m

$520

EvansvilleMontego Bay

EVV - MBJ

EVVMBJ

Evansville Dress Regional

Sat 7/4

10:18 am-3:34 pm

1 stop5h 16m

Montego Bay Sangster Intl

Thu 7/9

4:59 pm-9:26 am

1 stop16h 27m

$525

EvansvillePunta Cana

EVV - PUJ

EVVPUJ

Evansville Dress Regional

Thu 7/23

8:16 pm-8:25 pm

1 stop23h 09m

Punta Cana

Fri 7/31

3:44 pm-3:49 pm

2 stops25h 05m

$724

Flights are sorted by cheapest round-trip flights first.

Sorted 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	5h 37m
Direct flights	None

The fastest flight from Evansville to Caribbean Islands takes 5h 37m

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 May 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 A220-300, making up 20.08% of the total bookings. Other popular models include Boeing 737 MAX 8 with 14.86%, Canadair (Bombardier) Regional Jet 900 with 14.06%, and Airbus A319 with 11.24%.

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 11,654 reviews		Search American Airlines flights
Delta	PriceFrom $446	Free Cancellation	Rating 7.9 8,453 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.