$101 Find Cheap Flights from Caribbean Islands to Cleveland

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Cleveland departing on 4/13. 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

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Cheap Flights from Caribbean Islands to Cleveland

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Caribbean Islands to Cleveland 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 Caribbean Islands to Cleveland

Sat, May 30 - Tue, Jun 2
Frontier Logo
4:45 pm - 12:38 am
SJU
-
CLE
7h 53m
1 stop
Frontier Logo
3:42 pm - 4:49 am
CLE
-
SJU
13h 07m
1 stop
$192Frontier
Thu, May 14 - Wed, May 27
Frontier Logo
5:39 pm - 12:38 am
SJU
-
CLE
6h 59m
1 stop
Frontier Logo
9:57 pm - 8:04 am
CLE
-
SJU
10h 07m
1 stop
$210Frontier
Thu, May 7 - Sun, May 10
Frontier Logo
8:30 am - 9:25 pm
SJU
-
CLE
12h 55m
1 stop
Frontier Logo
2:14 pm - 2:08 am
CLE
-
SJU
11h 54m
1 stop
$211Frontier
Fri, May 8 - Sun, May 10
United Airlines Logo
2:10 pm - 10:44 pm
STT
-
CLE
8h 34m
1 stop
United Airlines Logo
6:00 am - 12:20 pm
CLE
-
STT
6h 20m
1 stop
$290United Airlines
Thu, Apr 30 - Thu, May 7
United Airlines Logo
4:12 pm - 11:59 pm
MBJ
-
CLE
6h 47m
1 stop
United Airlines Logo
3:06 pm - 3:10 pm
CLE
-
MBJ
25h 04m
1 stop
$312United Airlines
Mon, May 11 - Thu, Aug 20
American Airlines Logo
10:17 am - 12:26 am
MBJ
-
CLE
13h 09m
1 stop
American Airlines Logo
7:36 pm - 9:25 am
CLE
-
MBJ
14h 49m
1 stop
$316American Airlines
Thu, Apr 30 - Thu, May 7
American Airlines Logo
12:56 pm - 12:26 am
MBJ
-
CLE
10h 30m
2 stops
American Airlines Logo
8:45 pm - 11:24 am
CLE
-
MBJ
15h 39m
2 stops
$321American Airlines
Tue, May 12 - Sun, Sep 13
Delta Logo
4:59 pm - 9:17 am
MBJ
-
CLE
15h 18m
1 stop
Delta Logo
6:00 am - 3:34 pm
CLE
-
MBJ
10h 34m
1 stop
$353Delta
Sun, May 10 - Mon, Aug 31
British Airways Logo
10:17 am - 9:15 am
MBJ
-
CLE
21h 58m
1 stop
British Airways Logo
5:00 am - 12:20 pm
CLE
-
MBJ
8h 20m
1 stop
$383British Airways
Wed, May 6 - Thu, Jun 4
Delta Logo
6:00 am - 11:46 pm
STI
-
CLE
17h 46m
1 stop
Delta Logo
7:05 am - 7:28 pm
CLE
-
STI
12h 23m
1 stop
$567Delta
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$101
Best time to beat the crowds with an average 14% drop in price.
Most popular time to fly and prices are also 15% lower on average.
Flight from San Juan Airport to Cleveland

FAQs for booking flights from Caribbean Islands to Cleveland

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

    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 Caribbean Islands to Cleveland.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Cleveland from 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 Caribbean Islands to Cleveland?

    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 to Cleveland with an airline and back to Caribbean Islands with another airline.

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

    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 to Cleveland from 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 3 airlines serving from Caribbean Islands to Cleveland

 
Need help choosing which airline to fly with from Caribbean Islands to Cleveland? 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.
7.9
DeltaOverall score based on 8296 reviews
7.8Entertainment
8.1Boarding
8.5Crew
7.9Comfort
7.2Food
Airline reviews

First class is comfortable. Enjoyed a movie and was able to relax compared to coach.

10.0 ExcellentAnonymous, Mar 2026
ATL - DTW
Read more Delta reviews

First class is comfortable. Enjoyed a movie and was able to relax compared to coach.

Loved flying First Class. Very comfortable. The seat was amazing. Enjoyed a movie and was able to relax so much better than in coach.

No pilots so we were two hours late taking off and then no gate agents when we arrived in Salt Lake.

We landed and sat on the tarmac for 45 minutes because they only have one gate at the airport and there was another plane running late so we had to wait

The WiFi was not working. That made for a long flight.

Absolutely no communication on why there's a delay and multiple flight time reschedules. I would have canceled the flight and drove back home if I known it was going to be rescheduled 3 or 4 times.

Another late night flight and MORE men belligerently drinking and yelling. I had to move from first to economy because they were so obnoxious and disruptive. Crazy to go from a cozy chair to cardboard when you were supposed to be in first. Delta allows was too much drinking which leads to belligerent behavior.

I was in first class and literally the men behind me were so aggressively loud I moved myself to economy. This has become so common on Delta - people using audio without headphones, and men on 12am / late night flights drinking and yelling to talk to each other which prevents anyone around them from resting. Pretty crazy to have to move from first to economy (poorer service, less comfort...). Wild wild. Looking into other airlines.

Love delta smaller commuter plane so no entertainment and paid wifi on MKE-LGA leg was extremely unreliable and slow

Stop changing gates. Stop cancelling flights Stop moving my seat.

Both our flights were delayed. Almost didn’t get in the second flight. Staff was rude to the bone.

Hopped on time for the flight only to get deplaned and delayed another 2.5 hours.

Terrible experience! delay 2 time and say i dont have ticket

Both my flight where delayed Had 25min to make it to my transfer flight

Would've been great if Lufthansa union cockpit pilots didn't strike for 2 days and caused a chaos to my returning plans to USA, and then after rebooking a flight 2 days later tge plane departed 35 min later. So I did not have a good experience.

Everything was on time and service on the flight was great!

The boarding in Buenos Aires (at the on ramp) was not great. They had to check every carry on. Not a United problem but was a Buenos Aires problem.

Staff and aircraft were good. However, weather in Houston lee to a ground stop. We were looking at circling behind three other planes until the stop was lifted. Pilot said we didn’t have enough fuel for that. So we flew on to New Orleans as the closest port with immigration and customs staff. Landed there and sat in the plane for two hours plus while staff was sorted. Turned away by ICE. Waited for pilots to be switched out, but after they were approved by ICE. Then had to wait to get a runway because so many planes were ahead of us. Finally took off and flew back to Houston. We all missed our connecting flights because it took too long. Hotel voucher from United was only a link to booking site. Total BS. Finally got a flight out the next day after a night without sleep because all the Houston hotels were booked by rodeo and spring break crowds.

Wifi Bluetooth features for watching in flight movie was horrible. Screen kept blacking out no connection of sound although it said connected. Other than that smooth trip .

I paid $7,000 to fly round trip to Porto. I thought it was for business class. But on the leg from Miami to Newark, and again from Newark to Miami, i was in coach. One time in the middle seat of coach. From Newark to Porto I was in business class as expected, and it was fine. I fly to Portugal once per month, often paying $5,000 for business class. Usually i fly American Airlines. I'd be happy to fly more with United Airlines. But my experience was disappointing because i was put in the coach for almost half the flights.

Delay after delay with little communication then AA lost my luggage and at airport would not assist just said scan this QR code to track your luggage and submit a claim. However QR code provided did not work so have to go back to airport

After changing the departure gate 5 times making us mo e from one side of the airport to the other and then back the flight was delayed nearly 2 hours. The male flight attendant had a bad attitude with the guest being condescending, disrespectful with people who were already on edge.

Easy boarding. Rows are smaller but that may be an older and bigger me now :)

It would have been nice if American tried to care.

American Airlines did everything they could with the high Spring Break crowd. I was frustrated to be changed from 1st class to a middle seat at the back of the plane. This has happened before, not sure booking 1st class and paying the extra actually works.

I booked 1st class, my flights were changed and I was sitting in the middle at the back of the plane. A far cry from the 1st class I purchased for my flights. I am grateful I arrived on time.

Movie selections were very limited. Meals were not f So good.

Older airplane with worn out seats. No entertainment system at all. Connecting to Wi-Fi was problematic and hit and miss.

AA is flying sub par aging 787's to Tokyo. I fly other 787's long haul and these are at the bottom. Seats don't work well, tray tables don't work well and were dirty. The flight was great, the plane was not.

There was no beverage service and the only time I saw a crew member walk through the cabin is when we were preparing to land.

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