What airlines fly to Caribbean?

American Airlines, Delta and Southwest are the top three most popular airlines that fly to Caribbean 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. Keep in mind that there are 4 different airlines that fly to Caribbean 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?

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

When did momondo last update prices for flights from Evansville Dress Regional Airport to Caribbean?

Prices for flights from Evansville Dress Regional Airport to Caribbean were last updated today.

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

As of November 2026, there are 2 operators available to choose from for flights from Evansville Dress Regional Airport to Caribbean.

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

Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Evansville Dress Regional Airport to Caribbean.

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

The required travel and health documents for your Caribbean trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Caribbean. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

$213 Cheap Flights from Evansville to Caribbean in 2026/27

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Evansville to Caribbean

Round-trip

One-way

Last minute

Cheap round-trip flights

Enter your travel dates to find the best prices.

2:44 pm - 1:25 amEVV Evansville Dress Regional-SJU San Juan Luis Munoz Marin Intl

8h 41m1 stop Chicago O'Hare Intl

8:12 am - 8:33 pmSJU San Juan Luis Munoz Marin Intl-EVV Evansville Dress Regional

14h 21m2 stops Miami Charlotte Douglas

$426American Airlines

Sat, Mar 6 - Wed, Mar 10

2:44 pm - 1:25 amEVV Evansville Dress Regional-SJU San Juan Luis Munoz Marin Intl

8h 41m1 stop Chicago O'Hare Intl

6:10 am - 3:55 pmSJU San Juan Luis Munoz Marin Intl-EVV Evansville Dress Regional

11h 45m1 stop Chicago O'Hare Intl

$426American Airlines

Sat, Mar 6 - Wed, Mar 10

2:44 pm - 1:25 amEVV Evansville Dress Regional-SJU San Juan Luis Munoz Marin Intl

8h 41m1 stop Chicago O'Hare Intl

6:10 am - 3:55 pmSJU San Juan Luis Munoz Marin Intl-EVV Evansville Dress Regional

11h 45m1 stop Chicago O'Hare Intl

$426American Airlines

Sat, Mar 6 - Thu, Mar 11

4:47 pm - 10:41 amEVV Evansville Dress Regional-SJU San Juan Luis Munoz Marin Intl

15h 54m2 stops Charlotte Douglas Miami

7:00 am - 1:29 pmSJU San Juan Luis Munoz Marin Intl-EVV Evansville Dress Regional

8h 29m1 stop Charlotte Douglas

$446American Airlines

Mon, Nov 30 - Mon, Dec 7

8:31 pm - 8:35 pmEVV Evansville Dress Regional-PUJ Punta Cana

22h 04m1 stop Orlando Sanford Intl

7:19 pm - 4:02 pmPUJ Punta Cana-EVV Evansville Dress Regional

22h 43m2 stops San Juan Luis Munoz Marin Intl Orlando

$473Multiple Airlines

Thu, Dec 3 - Tue, Dec 8

8:30 pm - 4:51 pmEVV Evansville Dress Regional-SJU San Juan Luis Munoz Marin Intl

18h 21m1 stop Tampa St. Petersburg

3:57 pm - 7:35 pmSJU San Juan Luis Munoz Marin Intl-EVV Evansville Dress Regional

29h 38m1 stop Orlando

$528Multiple Airlines

Wed, Nov 25 - Sun, Nov 29

4:42 pm - 2:13 amEVV Evansville Dress Regional-SJU San Juan Luis Munoz Marin Intl

7h 31m1 stop Orlando

3:59 am - 4:02 pmSJU San Juan Luis Munoz Marin Intl-EVV Evansville Dress Regional

38h 03m2 stops Cleveland Hopkins Intl Orlando

$697Multiple Airlines

Wed, Dec 16 - Thu, Dec 31

10:09 am - 8:56 pmEVV Evansville Dress Regional-SJU San Juan Luis Munoz Marin Intl

8h 47m1 stop Atlanta Hartsfield-Jackson

7:45 am - 5:16 pmSJU San Juan Luis Munoz Marin Intl-EVV Evansville Dress Regional

11h 31m1 stop Atlanta Hartsfield-Jackson

$719Delta

Sat, Jan 16 - Sun, Jan 24

6:00 am - 1:25 pmEVV Evansville Dress Regional-GGT Georgetown Exuma Intl

6h 25m1 stop Atlanta Hartsfield-Jackson

2:20 pm - 10:27 pmGGT Georgetown Exuma Intl-EVV Evansville Dress Regional

9h 07m1 stop Atlanta Hartsfield-Jackson

$950Delta

Mon, Mar 1 - Sat, Mar 6

6:00 am - 1:25 pmEVV Evansville Dress Regional-GGT Georgetown Exuma Intl

6h 25m1 stop Atlanta Hartsfield-Jackson

2:20 pm - 10:27 pmGGT Georgetown Exuma Intl-EVV Evansville Dress Regional

9h 07m1 stop Atlanta Hartsfield-Jackson

$1,142Delta

Mon, Mar 1 - Sat, Mar 6

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Delta flights from Evansville to Caribbean

Our best Delta deals on Evansville to Caribbean flight tickets

Delta

Jan 16

EVV10:09 amEvansville Dress Regional

8h 47m

1 stop

SJU8:56 pmSan Juan Luis Munoz Marin Intl

Jan 24

SJU7:45 amSan Juan Luis Munoz Marin Intl

11h 31m

1 stop

EVV5:16 pmEvansville Dress Regional

$719

Delta

Mar 1

EVV6:00 amEvansville Dress Regional

6h 25m

1 stop

GGT1:25 pmGeorgetown Exuma Intl

Mar 6

GGT2:20 pmGeorgetown Exuma Intl

9h 07m

1 stop

EVV10:27 pmEvansville Dress Regional

$950

Delta

Mar 1

EVV6:00 amEvansville Dress Regional

6h 25m

1 stop

GGT1:25 pmGeorgetown Exuma Intl

Mar 6

GGT2:20 pmGeorgetown Exuma Intl

9h 07m

1 stop

EVV10:27 pmEvansville Dress Regional

$1,142

American Airlines flights from Evansville to Caribbean

Our best American Airlines deals on Evansville to Caribbean flight tickets

American Airlines

Mar 6

EVV2:44 pmEvansville Dress Regional

8h 41m

1 stop

SJU1:25 amSan Juan Luis Munoz Marin Intl

Mar 11

SJU6:10 amSan Juan Luis Munoz Marin Intl

11h 45m

1 stop

EVV3:55 pmEvansville Dress Regional

$426

American Airlines

Nov 30

EVV4:47 pmEvansville Dress Regional

15h 54m

2 stops

SJU10:41 amSan Juan Luis Munoz Marin Intl

Dec 7

SJU7:00 amSan Juan Luis Munoz Marin Intl

8h 29m

1 stop

EVV1:29 pmEvansville Dress Regional

$446

American Airlines

Jan 12

EVV6:13 amEvansville Dress Regional

8h 05m

1 stop

MBJ3:18 pmMontego Bay Sangster Intl

Feb 9

MBJ3:35 pmMontego Bay Sangster Intl

21h 07m

2 stops

EVV11:42 amEvansville Dress Regional

$458

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 3/6

2:44 pm-1:25 am

1 stop8h 41m

San Juan Luis Munoz Marin Intl

Wed 3/10

8:12 am-8:33 pm

2 stops14h 21m

$426

EvansvilleSan Juan

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

EVVSJU

Evansville Dress Regional

Sat 3/6

2:44 pm-1:25 am

1 stop8h 41m

San Juan Luis Munoz Marin Intl

Wed 3/10

6:10 am-3:55 pm

1 stop11h 45m

$426

EvansvilleSan Juan

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

EVVSJU

Evansville Dress Regional

Sat 3/6

2:44 pm-1:25 am

1 stop8h 41m

San Juan Luis Munoz Marin Intl

Thu 3/11

6:10 am-3:55 pm

1 stop11h 45m

$426

EvansvilleSan Juan

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

EVVSJU

Evansville Dress Regional

Mon 11/30

4:47 pm-10:41 am

2 stops15h 54m

San Juan Luis Munoz Marin Intl

Mon 12/7

7:00 am-1:29 pm

1 stop8h 29m

$446

EvansvillePunta Cana

EVV Evansville Dress Regional - PUJ Punta Cana

EVVPUJ

Evansville Dress Regional

Thu 12/3

8:31 pm-8:35 pm

1 stop22h 04m

Punta Cana

Tue 12/8

7:19 pm-4:02 pm

2 stops22h 43m

$473

EvansvilleSan Juan

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

EVVSJU

Evansville Dress Regional

Wed 11/25

8:30 pm-4:51 pm

1 stop18h 21m

San Juan Luis Munoz Marin Intl

Sun 11/29

3:57 pm-7:35 pm

1 stop29h 38m

$528

EvansvilleSan Juan

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

EVVSJU

Evansville Dress Regional

Wed 12/16

4:42 pm-2:13 am

1 stop7h 31m

San Juan Luis Munoz Marin Intl

Thu 12/31

3:59 am-4:02 pm

2 stops38h 03m

$697

EvansvilleSan Juan

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

EVVSJU

Evansville Dress Regional

Sat 1/16

10:09 am-8:56 pm

1 stop8h 47m

San Juan Luis Munoz Marin Intl

Sun 1/24

7:45 am-5:16 pm

1 stop11h 31m

$719

Quickest round-trip

EvansvilleGeorgetown

EVV Evansville Dress Regional - GGT Georgetown Exuma Intl

EVVGGT

Evansville Dress Regional

Mon 3/1

6:00 am-1:25 pm

1 stop6h 25m

Georgetown Exuma Intl

Sat 3/6

2:20 pm-10:27 pm

1 stop9h 07m

$950

EvansvilleGeorgetown

EVV Evansville Dress Regional - GGT Georgetown Exuma Intl

EVVGGT

Evansville Dress Regional

Mon 3/1

6:00 am-1:25 pm

1 stop6h 25m

Georgetown Exuma Intl

Sat 3/6

2:20 pm-10:27 pm

1 stop9h 07m

$1,142

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 18 resultsSorted by cheapest first

How to get the cheapest flight ticket from Evansville to Caribbean

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 flights?

You could potentially save up to 41% on your flight if you consider stops on a Evansville to Caribbean flight.

Cheap Evansville to Caribbean flight deals and tips

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

Best Price Found	$213
Fastest flight time	5h 37m
Direct flights	None

The best one-way flight to Caribbean from Evansville in the past 72 hours is $213. The best round-trip flight deal from Evansville to Caribbean found on momondo in the last 72 hours is $426.

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

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

Search flight deals

Frequently asked questions about flying from Evansville to Caribbean

When did momondo last update prices for flights from Evansville Dress Regional Airport to Caribbean?
Prices for flights from Evansville Dress Regional Airport to Caribbean were last updated today.
How many operators does momondo search for flights from Evansville Dress Regional Airport to Caribbean?
As of November 2026, there are 2 operators available to choose from for flights from Evansville Dress Regional Airport to Caribbean.
How old do you have to be to fly from Evansville Dress Regional Airport to Caribbean?
Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Evansville Dress Regional Airport to Caribbean.
What documentation or ID do you need to fly to Caribbean?
The required travel and health documents for your Caribbean trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Caribbean. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

Best airlines flying from Evansville to Caribbean

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

Airline	Rating	Free Cancellation	Price
Delta	PriceFrom $336	Free Cancellation	Rating 7.8 8,698 reviews		Search Delta flights
American Airlines	PriceFrom $378	Free Cancellation	Rating 7.0 12,231 reviews		Search American Airlines flights

Why use momondo?

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

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Caribbean from Evansville.

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

Yes. All flights to Caribbean from Evansville on momondo can be compared and filtered by various policies on offer, including flexible booking.

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

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Evansville to Caribbean.

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

Of course. momondo tracks the price of Evansville to Caribbean flights. All you need is a valid email address and we will do the rest; it is that quick and easy.