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

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 52% 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 July 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.

$320 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

One-way

Last minute

Cheap round-trip flights

Enter your travel dates to find the best prices.

6:39 pm - 12:41 am

EVV

SJU

29h 02m

1 stop

9:02 am - 7:04 pm

SJU

EVV

11h 02m

1 stop

$320Multiple Airlines

Thu, Aug 6 - Thu, Aug 13

5:56 pm - 12:53 pm

EVV

MBJ

18h 57m

2 stops

12:16 pm - 11:48 am

MBJ

EVV

23h 32m

1 stop

$404American Airlines

Fri, Oct 2 - Fri, Oct 9

4:29 pm - 2:15 am

EVV

SJU

8h 46m

1 stop

10:48 pm - 3:49 pm

SJU

EVV

18h 01m

1 stop

$452Multiple Airlines

Sat, Aug 1 - Fri, Aug 7

5:56 pm - 12:53 pm

EVV

MBJ

18h 57m

2 stops

2:09 pm - 11:55 am

MBJ

EVV

21h 46m

2 stops

$462American Airlines

Thu, Sep 17 - Tue, Sep 22

12:25 pm - 4:16 pm

EVV

MBJ

27h 51m

1 stop

12:16 pm - 11:16 pm

MBJ

EVV

11h 00m

1 stop

$464American Airlines

Sat, Oct 3 - Fri, Oct 9

5:56 pm - 4:16 pm

EVV

MBJ

22h 20m

1 stop

2:09 pm - 11:55 am

MBJ

EVV

21h 46m

2 stops

$469American Airlines

Thu, Sep 17 - Tue, Sep 22

1:43 pm - 10:19 pm

EVV

SJU

7h 36m

1 stop

7:30 am - 1:10 pm

SJU

EVV

6h 40m

1 stop

$478Delta

Wed, Sep 30 - Wed, Oct 7

1:43 pm - 10:19 pm

EVV

SJU

7h 36m

1 stop

7:00 am - 1:03 pm

SJU

EVV

7h 03m

1 stop

$518Delta

Thu, Sep 17 - Tue, Sep 22

6:20 am - 2:35 pm

EVV

PUJ

31h 15m

2 stops

3:30 pm - 5:19 pm

PUJ

EVV

26h 49m

2 stops

$3,690WestJet

Tue, Oct 27 - Thu, Oct 29

10:04 am - 2:35 pm

EVV

PUJ

27h 31m

2 stops

3:30 pm - 5:19 pm

PUJ

EVV

26h 49m

2 stops

$3,694WestJet

Tue, Oct 27 - Thu, Oct 29

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Delta flights from Evansville to Caribbean

Our best Delta deals on Evansville to Caribbean flight tickets

Delta

Sep 30

EVV1:43 pmEvansville Dress Regional

7h 36m

1 stop

SJU10:19 pmSan Juan Luis Munoz Marin Intl

Oct 7

SJU7:30 amSan Juan Luis Munoz Marin Intl

6h 40m

1 stop

EVV1:10 pmEvansville Dress Regional

$478

Delta

Sep 17

EVV1:43 pmEvansville Dress Regional

7h 36m

1 stop

SJU10:19 pmSan Juan Luis Munoz Marin Intl

Sep 22

SJU7:00 amSan Juan Luis Munoz Marin Intl

7h 03m

1 stop

EVV1:03 pmEvansville Dress Regional

$518

Delta

Aug 11

EVV6:25 amEvansville Dress Regional

9h 13m

1 stop

SJU4:38 pmSan Juan Luis Munoz Marin Intl

Aug 18

SJU2:59 pmSan Juan Luis Munoz Marin Intl

8h 02m

1 stop

EVV10:01 pmEvansville Dress Regional

$582

American Airlines flights from Evansville to Caribbean

Our best American Airlines deals on Evansville to Caribbean flight tickets

American Airlines

Oct 2

EVV5:56 pmEvansville Dress Regional

18h 57m

2 stops

MBJ12:53 pmMontego Bay Sangster Intl

Oct 9

MBJ12:16 pmMontego Bay Sangster Intl

23h 32m

1 stop

EVV11:48 amEvansville Dress Regional

$404

American Airlines

Sep 17

EVV5:56 pmEvansville Dress Regional

18h 57m

2 stops

MBJ12:53 pmMontego Bay Sangster Intl

Sep 22

MBJ2:09 pmMontego Bay Sangster Intl

21h 46m

2 stops

EVV11:55 amEvansville Dress Regional

$462

American Airlines

Oct 3

EVV12:25 pmEvansville Dress Regional

27h 51m

1 stop

MBJ4:16 pmMontego Bay Sangster Intl

Oct 9

MBJ12:16 pmMontego Bay Sangster Intl

11h 00m

1 stop

EVV11:16 pmEvansville Dress Regional

$464

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

EvansvilleSan Juan

EVV - SJU

EVVSJU

Evansville Dress Regional

Thu 8/6

6:39 pm-12:41 am

1 stop29h 02m

San Juan Luis Munoz Marin Intl

Thu 8/13

9:02 am-7:04 pm

1 stop11h 02m

$320

EvansvilleMontego Bay

EVV - MBJ

EVVMBJ

Evansville Dress Regional

Fri 10/2

5:56 pm-12:53 pm

2 stops18h 57m

Montego Bay Sangster Intl

Fri 10/9

12:16 pm-11:48 am

1 stop23h 32m

$404

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

Fri 8/7

10:48 pm-3:49 pm

1 stop18h 01m

$452

EvansvilleMontego Bay

EVV - MBJ

EVVMBJ

Evansville Dress Regional

Thu 9/17

5:56 pm-12:53 pm

2 stops18h 57m

Montego Bay Sangster Intl

Tue 9/22

2:09 pm-11:55 am

2 stops21h 46m

$462

EvansvilleMontego Bay

EVV - MBJ

EVVMBJ

Evansville Dress Regional

Sat 10/3

12:25 pm-4:16 pm

1 stop27h 51m

Montego Bay Sangster Intl

Fri 10/9

12:16 pm-11:16 pm

1 stop11h 00m

$464

EvansvilleMontego Bay

EVV - MBJ

EVVMBJ

Evansville Dress Regional

Thu 9/17

5:56 pm-4:16 pm

1 stop22h 20m

Montego Bay Sangster Intl

Tue 9/22

2:09 pm-11:55 am

2 stops21h 46m

$469

Quickest round-trip

EvansvilleSan Juan

EVV - SJU

EVVSJU

Evansville Dress Regional

Wed 9/30

1:43 pm-10:19 pm

1 stop7h 36m

San Juan Luis Munoz Marin Intl

Wed 10/7

7:30 am-1:10 pm

1 stop6h 40m

$478

EvansvilleSan Juan

EVV - SJU

EVVSJU

Evansville Dress Regional

Thu 9/17

1:43 pm-10:19 pm

1 stop7h 36m

San Juan Luis Munoz Marin Intl

Tue 9/22

7:00 am-1:03 pm

1 stop7h 03m

$518

EvansvillePunta Cana

EVV - PUJ

EVVPUJ

Evansville Dress Regional

Tue 10/27

6:20 am-2:35 pm

2 stops31h 15m

Punta Cana

Thu 10/29

3:30 pm-5:19 pm

2 stops26h 49m

$3,690

EvansvillePunta Cana

EVV - PUJ

EVVPUJ

Evansville Dress Regional

Tue 10/27

10:04 am-2:35 pm

2 stops27h 31m

Punta Cana

Thu 10/29

3:30 pm-5:19 pm

2 stops26h 49m

$3,694

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

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, October 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 $285. If you don’t want to visit Caribbean in October, then you should wait until March to fly from Evansville, when ticket prices are also cheap, with an average price of $446.

Can stopping save me money on Evansville to Caribbean flights?

You could potentially save up to 19% 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

Fastest flight time	6h 00m
Direct flights	None

The fastest flight from Evansville to Caribbean takes 6h 00m

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 July 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 11,818 reviews		Search American Airlines flights
Delta	PriceFrom $326	Free Cancellation	Rating 7.8 8,474 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.