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 48% 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.

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 September 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.

$366 Cheap Flights from Evansville to Caribbean in 2026

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Evansville to Caribbean

Round-trip

Last minute

Cheap round-trip flights

Enter your travel dates to find the best prices.

1:26 pm - 9:24 amEVV Evansville Dress Regional-SJU San Juan Luis Munoz Marin Intl

18h 58m2 stops Charlotte Douglas Miami

6:00 am - 11:29 pmSJU San Juan Luis Munoz Marin Intl-EVV Evansville Dress Regional

18h 29m2 stops Miami Dallas/Fort Worth

$366American Airlines

Thu, Sep 24 - Mon, Sep 28

4:52 pm - 5:36 amEVV Evansville Dress Regional-SJU San Juan Luis Munoz Marin Intl

10h 44m1 stop Chicago O'Hare Intl

4:27 pm - 11:59 pmSJU San Juan Luis Munoz Marin Intl-EVV Evansville Dress Regional

9h 32m1 stop Chicago O'Hare Intl

$406American Airlines

Tue, Jan 5 - Thu, Jan 14

5:49 pm - 10:48 amEVV Evansville Dress Regional-SJU San Juan Luis Munoz Marin Intl

14h 59m2 stops Charlotte Douglas Miami

4:27 pm - 11:59 pmSJU San Juan Luis Munoz Marin Intl-EVV Evansville Dress Regional

9h 32m1 stop Chicago O'Hare Intl

$406American Airlines

Tue, Jan 5 - Thu, Jan 14

6:40 am - 2:52 pmEVV Evansville Dress Regional-MBJ Montego Bay Sangster Intl

7h 12m1 stop Chicago O'Hare Intl

1:02 pm - 8:24 pmMBJ Montego Bay Sangster Intl-EVV Evansville Dress Regional

8h 22m1 stop Charlotte Douglas

$412American Airlines

Fri, Nov 13 - Wed, Nov 18

10:05 am - 9:00 pmEVV Evansville Dress Regional-SJU San Juan Luis Munoz Marin Intl

8h 55m1 stop Atlanta Hartsfield-Jackson

7:30 am - 4:54 pmSJU San Juan Luis Munoz Marin Intl-EVV Evansville Dress Regional

11h 24m1 stop Atlanta Hartsfield-Jackson

$494Delta

Sat, Jan 16 - Sun, Jan 24

1:43 pm - 10:19 pmEVV Evansville Dress Regional-SJU San Juan Luis Munoz Marin Intl

7h 36m1 stop Atlanta Hartsfield-Jackson

7:00 am - 1:03 pmSJU San Juan Luis Munoz Marin Intl-EVV Evansville Dress Regional

7h 03m1 stop Atlanta Hartsfield-Jackson

$624Delta

Thu, Sep 24 - Mon, Sep 28

6:00 am - 4:15 pmEVV Evansville Dress Regional-STT Saint Thomas Island Cyril E King

8h 15m1 stop Atlanta Hartsfield-Jackson

3:10 pm - 10:03 pmSTT Saint Thomas Island Cyril E King-EVV Evansville Dress Regional

8h 53m1 stop Atlanta Hartsfield-Jackson

$703Delta

Sat, Jan 30 - Fri, Feb 5

6:00 am - 2:35 pmEVV Evansville Dress Regional-SDQ Santo Domingo Las Americas

6h 35m1 stop Atlanta Hartsfield-Jackson

4:00 pm - 10:13 pmSDQ Santo Domingo Las Americas-EVV Evansville Dress Regional

8h 13m1 stop Atlanta Hartsfield-Jackson

$740JetBlue

Thu, Dec 24 - Sun, Jan 3

10:05 am - 5:20 pmEVV Evansville Dress Regional-MBJ Montego Bay Sangster Intl

30h 15m2 stops Atlanta Hartsfield-Jackson Calgary

8:35 pm - 4:54 pmMBJ Montego Bay Sangster Intl-EVV Evansville Dress Regional

21h 19m2 stops Toronto Pearson Intl Atlanta Hartsfield-Jackson

$1,644WestJet

Mon, Feb 1 - Fri, Feb 5

10:05 am - 5:20 pmEVV Evansville Dress Regional-MBJ Montego Bay Sangster Intl

30h 15m2 stops Atlanta Hartsfield-Jackson Calgary

8:35 pm - 4:54 pmMBJ Montego Bay Sangster Intl-EVV Evansville Dress Regional

21h 19m2 stops Toronto Pearson Intl Atlanta Hartsfield-Jackson

$1,671WestJet

Mon, Feb 1 - Fri, Feb 5

Cheap last minute flights

Enter your travel dates to find the best prices.

6:00 am - 6:44 pmEVV Evansville Dress Regional-SDQ Santo Domingo Las Americas

11h 44m2 stops Chicago O'Hare Intl Miami

7:00 am - 11:59 pmSDQ Santo Domingo Las Americas-EVV Evansville Dress Regional

17h 59m2 stops Miami Chicago O'Hare Intl

$1,248American Airlines

Fri, Sep 4 - Mon, Sep 7

6:00 am - 6:44 pmEVV Evansville Dress Regional-SDQ Santo Domingo Las Americas

11h 44m2 stops Dallas/Fort Worth Miami

7:00 am - 11:59 pmSDQ Santo Domingo Las Americas-EVV Evansville Dress Regional

17h 59m2 stops Miami Chicago O'Hare Intl

$1,286American Airlines

Sat, Sep 5 - Mon, Sep 7

6:25 am - 1:28 pmEVV Evansville Dress Regional-SDQ Santo Domingo Las Americas

6h 03m1 stop Atlanta Hartsfield-Jackson

2:53 pm - 10:01 pmSDQ Santo Domingo Las Americas-EVV Evansville Dress Regional

8h 08m1 stop Atlanta Hartsfield-Jackson

$1,702Delta

Sat, Sep 5 - Mon, Sep 7

6:25 am - 6:06 pmEVV Evansville Dress Regional-SDQ Santo Domingo Las Americas

10h 41m2 stops Atlanta Hartsfield-Jackson New York John F Kennedy Intl

2:53 pm - 10:01 pmSDQ Santo Domingo Las Americas-EVV Evansville Dress Regional

8h 08m1 stop Atlanta Hartsfield-Jackson

$1,707Delta

Sat, Sep 5 - Mon, Sep 7

10:04 am - 12:54 amEVV Evansville Dress Regional-SDQ Santo Domingo Las Americas

13h 50m2 stops Atlanta Hartsfield-Jackson New York John F Kennedy Intl

2:53 pm - 10:01 pmSDQ Santo Domingo Las Americas-EVV Evansville Dress Regional

8h 08m1 stop Atlanta Hartsfield-Jackson

$1,713Delta

Fri, Sep 4 - Mon, Sep 7

6:25 am - 1:28 pmEVV Evansville Dress Regional-SDQ Santo Domingo Las Americas

6h 03m1 stop Atlanta Hartsfield-Jackson

2:53 pm - 10:01 pmSDQ Santo Domingo Las Americas-EVV Evansville Dress Regional

8h 08m1 stop Atlanta Hartsfield-Jackson

$1,890Delta

Fri, Sep 4 - Mon, Sep 7

5:15 am - 6:44 pmEVV Evansville Dress Regional-SDQ Santo Domingo Las Americas

12h 29m3 stops Charlotte Douglas Tampa Miami

4:24 pm - 1:25 pmSDQ Santo Domingo Las Americas-EVV Evansville Dress Regional

22h 01m2 stops Miami Charlotte Douglas

$3,076American Airlines

Sat, Sep 5 - Mon, Sep 7

6:00 am - 6:44 pmEVV Evansville Dress Regional-SDQ Santo Domingo Las Americas

11h 44m3 stops Dallas/Fort Worth Tampa Miami

7:00 am - 4:31 pmSDQ Santo Domingo Las Americas-EVV Evansville Dress Regional

10h 31m2 stops Miami Dallas/Fort Worth

$3,237American Airlines

Fri, Sep 4 - Mon, Sep 7

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American Airlines flights from Evansville to Caribbean

Our best American Airlines deals on Evansville to Caribbean flight tickets

American Airlines

Sep 24

EVV1:26 pmEvansville Dress Regional

18h 58m

2 stops

SJU9:24 amSan Juan Luis Munoz Marin Intl

Sep 28

SJU6:00 amSan Juan Luis Munoz Marin Intl

18h 29m

2 stops

EVV11:29 pmEvansville Dress Regional

$366

American Airlines

Nov 13

EVV6:40 amEvansville Dress Regional

7h 12m

1 stop

MBJ2:52 pmMontego Bay Sangster Intl

Nov 18

MBJ1:02 pmMontego Bay Sangster Intl

8h 22m

1 stop

EVV8:24 pmEvansville Dress Regional

$412

American Airlines

Jan 12

EVV6:30 amEvansville Dress Regional

7h 29m

1 stop

MBJ2:59 pmMontego Bay Sangster Intl

Feb 9

MBJ1:26 pmMontego Bay Sangster Intl

9h 08m

1 stop

EVV9:34 pmEvansville Dress Regional

$413

Delta flights from Evansville to Caribbean

Our best Delta deals on Evansville to Caribbean flight tickets

Delta

Jan 16

EVV10:05 amEvansville Dress Regional

8h 55m

1 stop

SJU9:00 pmSan Juan Luis Munoz Marin Intl

Jan 24

SJU7:30 amSan Juan Luis Munoz Marin Intl

11h 24m

1 stop

EVV4:54 pmEvansville Dress Regional

$494

Delta

Sep 24

EVV1:43 pmEvansville Dress Regional

7h 36m

1 stop

SJU10:19 pmSan Juan Luis Munoz Marin Intl

Sep 28

SJU7:00 amSan Juan Luis Munoz Marin Intl

7h 03m

1 stop

EVV1:03 pmEvansville Dress Regional

$624

Delta

Jan 30

EVV6:00 amEvansville Dress Regional

8h 15m

1 stop

STT4:15 pmSaint Thomas Island Cyril E King

Feb 5

STT3:10 pmSaint Thomas Island Cyril E King

8h 53m

1 stop

EVV10:03 pmEvansville Dress Regional

$703

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

Thu 9/24

1:26 pm-9:24 am

2 stops18h 58m

San Juan Luis Munoz Marin Intl

Mon 9/28

6:00 am-11:29 pm

2 stops18h 29m

$366

EvansvilleSan Juan

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

EVVSJU

Evansville Dress Regional

Tue 1/5

4:52 pm-5:36 am

1 stop10h 44m

San Juan Luis Munoz Marin Intl

Thu 1/14

4:27 pm-11:59 pm

1 stop9h 32m

$406

EvansvilleSan Juan

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

EVVSJU

Evansville Dress Regional

Tue 1/5

5:49 pm-10:48 am

2 stops14h 59m

San Juan Luis Munoz Marin Intl

Thu 1/14

4:27 pm-11:59 pm

1 stop9h 32m

$406

EvansvilleMontego Bay

EVV Evansville Dress Regional - MBJ Montego Bay Sangster Intl

EVVMBJ

Evansville Dress Regional

Fri 11/13

6:40 am-2:52 pm

1 stop7h 12m

Montego Bay Sangster Intl

Wed 11/18

1:02 pm-8:24 pm

1 stop8h 22m

$412

EvansvilleSan Juan

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

EVVSJU

Evansville Dress Regional

Sat 1/16

10:05 am-9:00 pm

1 stop8h 55m

San Juan Luis Munoz Marin Intl

Sun 1/24

7:30 am-4:54 pm

1 stop11h 24m

$494

Quickest round-trip

EvansvilleSan Juan

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

EVVSJU

Evansville Dress Regional

Thu 9/24

1:43 pm-10:19 pm

1 stop7h 36m

San Juan Luis Munoz Marin Intl

Mon 9/28

7:00 am-1:03 pm

1 stop7h 03m

$624

EvansvilleSaint Thomas Island

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

EVVSTT

Evansville Dress Regional

Sat 1/30

6:00 am-4:15 pm

1 stop8h 15m

Saint Thomas Island Cyril E King

Fri 2/5

3:10 pm-10:03 pm

1 stop8h 53m

$703

EvansvilleSanto Domingo

EVV Evansville Dress Regional - SDQ Santo Domingo Las Americas

EVVSDQ

Evansville Dress Regional

Thu 12/24

6:00 am-2:35 pm

1 stop6h 35m

Santo Domingo Las Americas

Sun 1/3

4:00 pm-10:13 pm

1 stop8h 13m

$740

EvansvilleMontego Bay

EVV Evansville Dress Regional - MBJ Montego Bay Sangster Intl

EVVMBJ

Evansville Dress Regional

Mon 2/1

10:05 am-5:20 pm

2 stops30h 15m

Montego Bay Sangster Intl

Fri 2/5

8:35 pm-4:54 pm

2 stops21h 19m

$1,644

EvansvilleMontego Bay

EVV Evansville Dress Regional - MBJ Montego Bay Sangster Intl

EVVMBJ

Evansville Dress Regional

Mon 2/1

10:05 am-5:20 pm

2 stops30h 15m

Montego Bay Sangster Intl

Fri 2/5

8:35 pm-4:54 pm

2 stops21h 19m

$1,671

Flights are sorted by cheapest round-trip flights first.

Sorted 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

What is the cheapest month to fly to Caribbean?

In general, September is the cheapest month to fly from Evansville to Caribbean. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $0. If you don’t want to visit Caribbean in September, then you should wait until April to fly from Evansville, when ticket prices are also cheap, with an average price of $0.

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	$366
Fastest flight time	6h 09m
Direct flights	None

The best flight deal from Evansville to Caribbean found on momondo in the last 72 hours is $366

The fastest flight from Evansville to Caribbean takes 6h 09m

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 September 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
American Airlines	PriceFrom $285	Free Cancellation	Rating 7.1 12,023 reviews		Search American Airlines flights
Delta	PriceFrom $336	Free Cancellation	Rating 7.8 8,538 reviews		Search Delta 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.