CLE - SXM

$493 Find Cheap Flights from Cleveland to Simpson Bay - Compare and Save

This is the cheapest round-trip flight price found by a KAYAK user in the last 72 hours by searching for a flight from Cleveland to Simpson Bay departing on 8/3. 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 Simpson Bay

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Cleveland to Simpson Bay, 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 Cleveland to Simpson Bay, as well as popular online travel agencies
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Everything you should know

Cheapest round-trip
$493
Typical prices: $756-$486
American Airlines
Mon 8/3Thu 8/13
CLE - SXM • 1 stop
Top airlines
Cheapest • from $493 (round-trip)
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Not available
There are currently no direct flights between Cleveland and Simpson Bay. You'll need at least 1 connection.
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $481 (round-trip)
Shortest trip • 6h 33m (one-way)
Insights
Insights
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 2 weeks in advance save around 24% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 24% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Simpson Bay!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Cleveland to Simpson Bay (CLE-SXM)

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

Mon, Aug 3 - Thu, Aug 13
American Airlines Logo
6:01 am - 3:44 pm
CLE
-
SXM
9h 43m
1 stop
American Airlines Logo
2:42 pm - 11:38 pm
SXM
-
CLE
8h 56m
1 stop
$493American Airlines
Mon, Aug 3 - Thu, Aug 13
American Airlines Logo
8:47 pm - 3:44 pm
CLE
-
SXM
18h 57m
2 stops
American Airlines Logo
2:42 pm - 11:38 pm
SXM
-
CLE
8h 56m
1 stop
$498American Airlines
Sat, Jul 4 - Tue, Jul 7
American Airlines Logo
11:39 am - 1:51 pm
CLE
-
SXM
26h 12m
1 stop
American Airlines Logo
2:51 pm - 12:29 am
SXM
-
CLE
9h 38m
1 stop
$501American Airlines
Wed, Jul 8 - Tue, Jul 14
American Airlines Logo
5:01 am - 1:34 pm
CLE
-
SXM
8h 33m
1 stop
American Airlines Logo
2:51 pm - 8:16 am
SXM
-
CLE
17h 25m
2 stops
$503American Airlines
Sat, Jul 18 - Tue, Jul 21
American Airlines Logo
7:08 pm - 1:19 pm
CLE
-
SXM
18h 11m
1 stop
American Airlines Logo
4:45 pm - 6:38 pm
SXM
-
CLE
25h 53m
1 stop
$504American Airlines
Thu, Nov 26 - Sat, Dec 5
American Airlines Logo
1:23 pm - 2:00 pm
CLE
-
SXM
23h 37m
1 stop
American Airlines Logo
5:25 pm - 10:30 am
SXM
-
CLE
18h 05m
2 stops
$505American Airlines
Wed, Aug 5 - Sun, Aug 9
American Airlines Logo
6:15 am - 3:39 pm
CLE
-
SXM
9h 24m
1 stop
American Airlines Logo
2:22 pm - 9:35 am
SXM
-
CLE
19h 13m
2 stops
$508American Airlines
Thu, Jul 23 - Mon, Jul 27
American Airlines Logo
7:08 pm - 3:44 pm
CLE
-
SXM
20h 36m
1 stop
American Airlines Logo
4:45 pm - 11:12 am
SXM
-
CLE
18h 27m
2 stops
$509American Airlines
Sun, Aug 23 - Thu, Aug 27
JetBlue Logo
6:25 am - 1:42 pm
CLE
-
SXM
7h 17m
1 stop
JetBlue Logo
1:42 pm - 11:59 pm
SXM
-
CLE
10h 17m
1 stop
$521JetBlue
Sat, Jun 27 - Thu, Jul 2
American Airlines Logo
5:45 am - 1:50 pm
CLE
-
SXM
8h 05m
1 stop
American Airlines Logo
2:51 pm - 12:29 am
SXM
-
CLE
9h 38m
1 stop
$524American Airlines
Booking Insights

KAYAK's insights & trends for Cleveland to Simpson Bay flights

Get data-powered insights and trends into flights from Cleveland to Simpson Bay to help you find the cheapest flights, the best time to fly and much more.

How much is a round-trip flight from Cleveland to Simpson Bay?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Cleveland to Simpson Bay departing in August.

What is the cheapest month to fly from Cleveland to Simpson Bay?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Cleveland to Simpson Bay, 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 Cleveland to Simpson Bay is July, where tickets cost $498 (return) on average. On the other hand, the most expensive months are December and February, where the average cost of round-trip tickets is $775 and $755 respectively.

How far in advance should I book a flight from Cleveland to Simpson Bay?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Cleveland to Simpson Bay, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Cleveland to Simpson Bay, you should book around 2 weeks before departure, which saves you about 24% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 12 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$493
Best time to beat the crowds but there is an average 7% increase in price.
Most popular time to fly with an average 15% increase in price.
Flight from Cleveland to Simpson Bay

When to book flights from Cleveland to Simpson Bay

Are your dates flexible? Find out the best times to travel from Cleveland to Simpson Bay based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking flights from Cleveland to Simpson Bay

  • What is the cheapest flight from Cleveland to Simpson Bay?

    In the last 5 days, the lowest price for a flight from Cleveland to Simpson Bay was $493 for a round-trip ticket.

  • Do I need a passport to fly between Cleveland and Simpson Bay?

    Yes, you'll most likely have to show a valid passport before boarding the plane in Cleveland and on arrival in Simpson Bay.

  • Which airports will I be using when flying from Cleveland to Simpson Bay?

    Cleveland and Simpson Bay are both served by 1 main airport. You will leave Cleveland from Cleveland Hopkins Intl and will be arriving at Simpson Bay Princess Juliana.

  • Which aircraft models fly most regularly from Cleveland to Simpson Bay?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Cleveland to Simpson Bay?

    Star Alliance, SkyTeam, and oneworld are the airline alliances operating flights between Cleveland and Simpson Bay, with Star Alliance being the most commonly used for this route.

  • Which is the best airline for flights from Cleveland to Simpson Bay, Delta or United Airlines?

    The two airlines most popular with KAYAK users for flights from Cleveland to Simpson Bay are Delta and United Airlines. With an average price for the route of $723 and an overall rating of 7.9, Delta is the most popular choice. United Airlines is also a great choice for the route, with an average price of $653 and an overall rating of 7.4.

  • How does KAYAK find such low prices on flights from Cleveland to Simpson Bay?

    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 Cleveland to Simpson Bay.

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

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

    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 Simpson Bay with an airline and back to Cleveland with another airline. Booking your flights between Cleveland and SXM can sometimes prove cheaper using this method.

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

    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 Simpson Bay from Cleveland 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 Cleveland to Simpson Bay

 
See real verified KAYAK customer reviews for airlines flying from Cleveland to Simpson Bay. 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 Cleveland to Simpson Bay? 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 8405 reviews
8.5Crew
8.1Boarding
7.8Entertainment
7.8Comfort
7.2Food
Airline reviews

Flight attendants were great. Cheerful, upbeat and friendly. Jet, in particular, was fantastic.

10.0 ExcellentJOSEPH, Jun 2026
RIC - ATL
Read more Delta reviews

Flight attendants were great. Cheerful, upbeat and friendly. Jet, in particular, was fantastic.

I have Precheck. Flew HPN to DEN and return this past weekend. Delta didn't attach my Precheck number to this trip. So it was waiting in general line especially in Denver. Unavailable.

Original flight was delayed, then cancelled and the gate staff did not expedite rebooking. Also, no instructions were given that a ticket number was needed before being called to facilitate rebooking. This could have been much more organized.

Be on time? When not on time a circling for over an hour offer more than 1 bag of chips to the passengers? It was a 7 hour flight by the time we got done.

Five hour delays every hour, I wish it were all at once

Flight delayed four separate times. I’m now one hour hours late to landing.

worst flight ever from Delta, it got delayed and kept on delaying..

Should never have had to go to Detroit from Orlando back to Tennessee!

Got rerouted from a straight flight from Orlando to Atlanta to Knoxville to a flight from Orlando to Detroit to Knoxville! Seriously!! Flight delay out of Detroit! Long day for what should have been a pretty easy travel day!

Two delays on two separate planes with parts they could not easily find and replace.

Horrible! Several delays and then was cancelled! I spent over 24 hours in the airport and was unable to get a hotel or food voucher.

The entertainment they offer could use some games, and maybe they could add some cookies to the snack menu. And the automated messages are a bit repetitive. But it was comfortable temperature wise and the seats were comfortable. The crew is very polite and helpful

The entertainment is a bit limited, it would be better if they added some games to play besides the movies and tv shows. But the seats are comfortable and the crew is polite

This planes staff was top tier. Everything went great and had a great flight home.

Food was great. Staff was phenomenal. Seats were a bit hard and could use a lot more entertainment options as far as movies to choose from. WiFi was good. Overall great trip.

This was an overnight flight, and in the morning they did know coffee service. How you can throw passengers in a San Francisco airport at 5:40 a.m. in the morning and not giving them Coffee is a crime.

I was promised by United Airline (operated by ANA) that I will be seated together with my kids as I am the only adult flying with two minors. We did not get seats together in our 11 hours flight from LA to Tokyo. When asked at the gate, ANA representative said United Airline should have informed them that there is a parent flying with two minors. He said they can’t do anything in the system as the flight is full. He ask me to ask passengers next to me and the kids if they are willing to change seats. This is ridiculous! However, I went in the flight and asked other passages but no one willing to change seats. 11 hours and we were seating separately. I was very disappointed with this. It made things super inconvenient for me.

Our flight was delayed several Times due to mechanical issues. Although I understand this may happen at times, it was very inconvenient and we had to book a hotel for an overnight stay. We were traveling with my 3-yo grandson and waiting at the airport from noon until 6:30pm with no reassurance that our next rescheduled flight would depart, we had to decide what’s best for him. A day later, I found out that I may be able to demand compensation if my flight is delayed more than 4 hours. I will hav to read the fine print next time.

Flight cancelled instead of leaving Friday am now, maybe, leaving Sunday

The pilot had to extend the flight time from san antonio to Houston to burn off fuel. This caused a lot of unnecessary stress since we had a tight connection to Aruba. And with no other flights going to Aruba we were worried about spending a night in Houston. We had to to run to our connection because of the flight crews mistake. Not happy.

Trash. Sat on the runway for 40 mins…missed connecting flight because of it now I’m stuck. Thanks…a whole fkn lot.

The flight was delayed significantly and we sat on runway after landing for awhile. Best thing was the flight attendant, Jenny, in first class, who was very professional and attentive. She was excellent - the rest of the flight was not.

Crew were professional and kind. The flight was smooth. But... The internet, which we paid 35 dollars for, did not work for most of the flight. This made providing media for our child an uncomfortable hassle.

Overall fine. Seemed like one of the older model planes? Crew was mostly very kind, though some of the female attendants were a rather abrupt during the food service.

Awfully rude American worker at door when we started boarding flight. Then, walk into a blazing hot airplane with no air conditioning until twenty minutes into the flight. Free entertainment was non existent! My husband, along with the fellow passenger in our row, and I could not get entertainment to work, no WIFI! Really?? Been flying American a long time. Was very disappointed.

Flight was delayed by 6 hours... the level of incompetence was truly astounding. I won't be flying American Airlines again. I don't care if AA is direct and there is a layover with another airline, I'll take the layover.

Leave on time. We waited on the plane for hour hours and it was hot and smelly

Two hours delay, probably one hour because they didn’t bring catering and they had to bring water in board. There a change of aircraft. But delays galore at CLT so it must be a CLT and/or AA operation issue. The 1 hr additional delays because nobody could bring 2 packs of water sooner is probably the best example of this airline operates

Flight was delayed 5 hours. Initial reason for delay was 'maintenance' - which makes sense. Then, the additional 2 hours continued to say it was maintenance - when I know EWR had a 2 hour delay. AA did not say that. Additionally, when boarding, there was only one agent at the counter for a long time - until another came to help. After boarding, we had to wait another 45 minutes due to 'no catering'. So while we waited for catering, AA continued to board additional passengers - which seemed odd - and raised questions about what really was going on. I sat in First Class. During the flight, the flight crew allowed a significant number of non-First Class passengers to use the front bathroom - which created a very crowded environment in First Class which was uncomfortable. This also delayed First Class passengers from using the bathroom. Overall, horrible experience.

The Charleston, WV airport was cute. Very good staff and small enough to feel comfortable. The plane had more leg room than bigger planes. Much more comfortable.

Everything you need to know for your flight from Cleveland to Simpson Bay

Information on your arrival and departure airports