$420 Find Cheap Flights from Evansville to Caribbean Islands

This is the cheapest round-trip flight price found by a KAYAK user in the last 72 hours by searching for a flight from Evansville to Caribbean Islands departing on 9/18. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Caribbean Islands

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Evansville to Caribbean Islands, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Evansville to Caribbean Islands, as well as popular online travel agencies
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Flight Deals

Cheap Flights from Evansville to Caribbean Islands

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana2 stops$573
Santo Domingo
Santo Domingo1 stop$625
Montego Bay
Montego Bay2 stops$3,690
Saint Thomas Island
Saint Thomas Island2 stops$420
Punta Cana
Punta Cana2 stops$573
Santo Domingo
Santo Domingo1 stop$625
Montego Bay
Montego Bay2 stops$3,690
Saint Thomas Island
Saint Thomas Island2 stops$420

Book Cheap Evansville to Caribbean Islands Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Evansville to Caribbean Islands that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Evansville to Caribbean Islands

Fri, Sep 18 - Wed, Sep 23
American Airlines Logo
7:29 am - 12:50 pm
EVV
-
STT
28h 21m
2 stops
American Airlines Logo
1:50 pm - 12:06 pm
STT
-
EVV
23h 16m
2 stops
$420American Airlines
Mon, Sep 28 - Sun, Oct 4
American Airlines Logo
6:04 pm - 12:50 pm
EVV
-
STT
17h 46m
2 stops
American Airlines Logo
1:50 pm - 9:54 am
STT
-
EVV
21h 04m
2 stops
$485American Airlines
Sat, Jun 13 - Thu, Jun 18
American Airlines Logo
4:34 pm - 11:02 am
EVV
-
SJU
17h 28m
2 stops
American Airlines Logo
12:57 am - 6:05 pm
SJU
-
EVV
18h 08m
1 stop
$499American Airlines
Sat, Jun 13 - Fri, Jun 19
American Airlines Logo
4:34 pm - 11:02 am
EVV
-
SJU
17h 28m
2 stops
American Airlines Logo
7:00 am - 6:05 pm
SJU
-
EVV
12h 05m
2 stops
$571American Airlines
Wed, Jul 8 - Tue, Jul 14
Delta Logo
6:22 am - 1:17 pm
EVV
-
SDQ
5h 55m
1 stop
Delta Logo
2:42 pm - 9:49 pm
SDQ
-
EVV
8h 07m
1 stop
$625Delta
Mon, Sep 28 - Sun, Oct 4
Delta Logo
6:00 am - 1:44 pm
EVV
-
STT
6h 44m
1 stop
Delta Logo
2:54 pm - 10:03 pm
STT
-
EVV
8h 09m
1 stop
$645Delta
Thu, Jul 23 - Fri, Jul 31
Multiple Airlines Logo
8:16 pm - 8:25 pm
EVV
-
PUJ
23h 09m
1 stop
Multiple Airlines Logo
3:44 pm - 3:49 pm
PUJ
-
EVV
25h 05m
2 stops
$724Multiple Airlines
Thu, Jul 23 - Sat, Aug 1
Multiple Airlines Logo
8:16 pm - 8:25 pm
EVV
-
PUJ
23h 09m
1 stop
Multiple Airlines Logo
7:10 pm - 10:51 am
PUJ
-
EVV
40h 41m
2 stops
$1,001Multiple Airlines
Tue, Sep 1 - Sat, Sep 5
WestJet Logo
5:45 pm - 11:45 am
EVV
-
MBJ
42h 00m
2 stops
WestJet Logo
7:30 pm - 10:03 pm
MBJ
-
EVV
26h 33m
2 stops
$3,690WestJet
Tue, Sep 1 - Sat, Sep 5
WestJet Logo
6:00 am - 11:45 am
EVV
-
MBJ
29h 45m
2 stops
WestJet Logo
7:30 pm - 12:51 pm
MBJ
-
EVV
17h 21m
2 stops
$3,744WestJet
Booking Insights

KAYAK's insights & trends for Evansville to Caribbean Islands flights

Get data-powered insights and trends into flights from Evansville to Caribbean Islands to help you find the cheapest flights, the best time to fly and much more.

Can I save money by flying with a layover from Evansville to Caribbean Islands?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $489, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Evansville to Caribbean Islands?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Evansville to Caribbean Islands, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Evansville to Caribbean Islands is November, when tickets cost $0 (return) on average. On the other hand, the most expensive months are May and February, when the average cost of round-trip tickets is $806 and $729 respectively.

Find deals

Good to know

Low seasonAugust
Cheapest flight$420
Best time to beat the crowds with an average 5% drop in price.
Most popular time to fly and prices are also 16% lower on average.
Flight from Evansville to Saint Thomas Island

FAQs - booking Caribbean Islands flights

  • How does KAYAK find such low prices on flights from Evansville to Caribbean Islands?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Evansville to Caribbean Islands.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Evansville to Caribbean Islands?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Evansville to Caribbean Islands is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Evansville to Caribbean Islands?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from Evansville to Caribbean Islands with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Evansville to Caribbean Islands?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Evansville to Caribbean Islands up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airline flying from Evansville to Caribbean Islands

 
See real verified KAYAK customer reviews for airlines flying from Evansville to Caribbean Islands. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Evansville to Caribbean Islands? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.1
American AirlinesOverall score based on 11664 reviews
7.9Crew
7.2Comfort
6.9Entertainment
6.4Food
7.5Boarding
Airline reviews

Seat comfort was poor (no lumbar or lower back support).

8.0 ExcellentAnonymous, May 2026
PIT - DFW
Read more American Airlines reviews

Seat comfort was poor (no lumbar or lower back support).

The airplane seats were spacious and comfortable, and the flight attendants were friendly and attentive. The food was delicious like never before. The blankets and toiletries were thoughtfully provided. The captain's navigation was steady and reliable. In short, having flown with Starlux, I won't consider any other airline next time.

STOP MAKING THE SEATING SO CRAMPED. WE NEED A PASSENGER BILL OF RIGHTS!

The passenger in front of of me reclined their seat back all the way the entire flight. Their headrest was in my face the entire flight! I barely had room for the little plastic cup of water to fit on my tray table; can you make the seats and space between the rows any smaller??? You can’t even get up to use the restroom! Worst flight I’ve had in a very long time!

We had several flights and they were all on-time and flawless

My Frequent Flyer nber wasn't put on as I was told it was..... This resulted in a last group boarding and no priority tags on My bags.

Premium Economy Good crew, good service, excellent food. Seat back screen just not bright enough.

Terrible steward... Plane was quite empty... I asked to move "back" in the plane and the steward said no... Unnecessary power trip of mediocre people.

Flight was delayed an no one cares, or try to help passengers to get the conexión.

Our flight was cancelled while we are on our way to the airport. So, no notice. We were rescheduled to another airline with a 2 hour later takeoff and so arrived at our destination on time. We pre-paid American Airlines $190 to upgrade our seats. No refund. So no use for AA or Kayak.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports

Evansville (EVV)