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 5 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?

Delta and American Airlines are the most popular carriers 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 April 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.

$128 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 - 12:13 pm

EVV

MBJ

17h 17m

2 stops

4:37 pm - 10:35 am

MBJ

EVV

17h 58m

2 stops

$357American Airlines

jue., may. 7 - mar., may. 12

7:46 pm - 8:53 am

EVV

SJU

12h 07m

1 stop

6:30 am - 7:06 pm

SJU

EVV

13h 36m

1 stop

$386Multiple Airlines

lun., abr. 13 - vie., abr. 17

7:46 pm - 6:55 pm

EVV

SJU

22h 09m

2 stops

10:54 am - 7:06 pm

SJU

EVV

9h 12m

1 stop

$390Multiple Airlines

lun., abr. 13 - vie., abr. 17

6:13 am - 8:55 pm

EVV

SJU

13h 42m

2 stops

6:20 am - 4:08 pm

SJU

EVV

10h 48m

2 stops

$408American Airlines

sáb., may. 16 - sáb., may. 23

6:23 pm - 12:13 pm

EVV

MBJ

17h 50m

1 stop

2:19 pm - 10:58 pm

MBJ

EVV

8h 39m

1 stop

$434American Airlines

jue., may. 7 - mar., may. 12

6:56 pm - 10:48 am

EVV

SJU

14h 52m

1 stop

7:00 am - 4:08 pm

SJU

EVV

10h 08m

1 stop

$448American Airlines

sáb., may. 16 - sáb., may. 23

6:18 am - 11:53 am

EVV

MBJ

5h 35m

1 stop

1:18 pm - 9:44 pm

MBJ

EVV

8h 26m

1 stop

$609Delta

vie., may. 15 - vie., may. 22

6:18 am - 3:17 pm

EVV

STT

7h 59m

1 stop

3:01 pm - 9:44 pm

STT

EVV

7h 43m

1 stop

$650Delta

mié., may. 20 - mié., may. 27

5:45 pm - 11:45 am

EVV

MBJ

42h 00m

2 stops

12:45 pm - 12:51 pm

MBJ

EVV

24h 06m

2 stops

$3,729WestJet

lun., sep. 14 - vie., sep. 18

5:45 pm - 11:45 am

EVV

MBJ

42h 00m

2 stops

12:45 pm - 12:51 pm

MBJ

EVV

24h 06m

2 stops

$3,739WestJet

lun., sep. 14 - vie., sep. 18

American Airlines flights from Evansville to Caribbean Islands

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

American Airlines

May 7

EVV6:56 pmEvansville Dress Regional

17h 17m

2 stops

MBJ12:13 pmMontego Bay Sangster Intl

May 12

MBJ4:37 pmMontego Bay Sangster Intl

17h 58m

2 stops

EVV10:35 amEvansville Dress Regional

$357

American Airlines

May 16

EVV6:13 amEvansville Dress Regional

13h 42m

2 stops

SJU8:55 pmSan Juan Luis Munoz Marin Intl

May 23

SJU6:20 amSan Juan Luis Munoz Marin Intl

10h 48m

2 stops

EVV4:08 pmEvansville Dress Regional

$408

American Airlines

May 7

EVV6:23 pmEvansville Dress Regional

17h 50m

1 stop

MBJ12:13 pmMontego Bay Sangster Intl

May 12

MBJ2:19 pmMontego Bay Sangster Intl

8h 39m

1 stop

EVV10:58 pmEvansville Dress Regional

$434

WestJet flights from Evansville to Caribbean Islands

Our best WestJet deals on Evansville to Caribbean Islands flight tickets

WestJet

Sep 14

EVV5:45 pmEvansville Dress Regional

42h 00m

2 stops

MBJ11:45 amMontego Bay Sangster Intl

Sep 18

MBJ12:45 pmMontego Bay Sangster Intl

24h 06m

2 stops

EVV12:51 pmEvansville Dress Regional

$3,729

WestJet

Sep 14

EVV5:45 pmEvansville Dress Regional

42h 00m

2 stops

MBJ11:45 amMontego Bay Sangster Intl

Sep 18

MBJ12:45 pmMontego Bay Sangster Intl

24h 06m

2 stops

EVV12:51 pmEvansville Dress Regional

$3,739

WestJet

Sep 14

EVV5:45 pmEvansville Dress Regional

42h 00m

2 stops

MBJ11:45 amMontego Bay Sangster Intl

Sep 18

MBJ12:45 pmMontego Bay Sangster Intl

24h 06m

2 stops

EVV12:51 pmEvansville Dress Regional

$3,745

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

jue. 5/7

6:56 pm-12:13 pm

2 stops17h 17m

Montego Bay Sangster Intl

mar. 5/12

4:37 pm-10:35 am

2 stops17h 58m

$357

EvansvilleSan Juan

EVV - SJU

EVVSJU

Evansville Dress Regional

lun. 4/13

7:46 pm-8:53 am

1 stop12h 07m

San Juan Luis Munoz Marin Intl

vie. 4/17

6:30 am-7:06 pm

1 stop13h 36m

$386

EvansvilleSan Juan

EVV - SJU

EVVSJU

Evansville Dress Regional

lun. 4/13

7:46 pm-6:55 pm

2 stops22h 09m

San Juan Luis Munoz Marin Intl

vie. 4/17

10:54 am-7:06 pm

1 stop9h 12m

$390

EvansvilleSan Juan

EVV - SJU

EVVSJU

Evansville Dress Regional

sáb. 5/16

6:13 am-8:55 pm

2 stops13h 42m

San Juan Luis Munoz Marin Intl

sáb. 5/23

6:20 am-4:08 pm

2 stops10h 48m

$408

EvansvilleMontego Bay

EVV - MBJ

EVVMBJ

Evansville Dress Regional

jue. 5/7

6:23 pm-12:13 pm

1 stop17h 50m

Montego Bay Sangster Intl

mar. 5/12

2:19 pm-10:58 pm

1 stop8h 39m

$434

EvansvilleSan Juan

EVV - SJU

EVVSJU

Evansville Dress Regional

sáb. 5/16

6:56 pm-10:48 am

1 stop14h 52m

San Juan Luis Munoz Marin Intl

sáb. 5/23

7:00 am-4:08 pm

1 stop10h 08m

$448

Quickest round-trip

EvansvilleMontego Bay

EVV - MBJ

EVVMBJ

Evansville Dress Regional

vie. 5/15

6:18 am-11:53 am

1 stop5h 35m

Montego Bay Sangster Intl

vie. 5/22

1:18 pm-9:44 pm

1 stop8h 26m

$609

EvansvilleSaint Thomas Island

EVV - STT

EVVSTT

Evansville Dress Regional

mié. 5/20

6:18 am-3:17 pm

1 stop7h 59m

Saint Thomas Island Cyril E King

mié. 5/27

3:01 pm-9:44 pm

1 stop7h 43m

$650

EvansvilleMontego Bay

EVV - MBJ

EVVMBJ

Evansville Dress Regional

lun. 9/14

5:45 pm-11:45 am

2 stops42h 00m

Montego Bay Sangster Intl

vie. 9/18

12:45 pm-12:51 pm

2 stops24h 06m

$3,729

EvansvilleMontego Bay

EVV - MBJ

EVVMBJ

Evansville Dress Regional

lun. 9/14

5:45 pm-11:45 am

2 stops42h 00m

Montego Bay Sangster Intl

vie. 9/18

12:45 pm-12:51 pm

2 stops24h 06m

$3,739

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	5h 35m
Direct flights	None

The fastest flight from Evansville to Caribbean Islands takes 5h 35m

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 April 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 24.01% of the total bookings. Other popular models include Boeing 737 MAX 8 with 23.30%, Airbus A319 with 10.39%, and Canadair (Bombardier) Regional Jet 900 with 9.32%.

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 11,544 reviews		Search American Airlines flights
Delta	PriceFrom $446	Free Cancellation	Rating 7.9 8,368 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.