CLE - SXM

$133 Find Cheap Flights from Cleveland to Simpson Bay

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Cleveland to Simpson Bay departing on 12/6. 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

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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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

Wed, Nov 12 - Wed, Nov 19
American Airlines Logo
6:06 am - 4:22 pmCLE-SXM
9h 16m1 stop
American Airlines Logo
2:51 pm - 11:49 pmSXM-CLE
9h 58m1 stop
$461American Airlines
Find Deal
Wed, Nov 12 - Wed, Nov 19
American Airlines Logo
6:00 am - 4:22 pmCLE-SXM
9h 22m2 stops
American Airlines Logo
2:51 pm - 11:49 pmSXM-CLE
9h 58m1 stop
$466American Airlines
Find Deal
Sat, Nov 29 - Fri, Dec 5
American Airlines Logo
1:23 pm - 2:00 pmCLE-SXM
23h 37m1 stop
American Airlines Logo
2:51 pm - 11:49 pmSXM-CLE
9h 58m1 stop
$469American Airlines
Find Deal
Sat, Nov 29 - Sat, Dec 6
American Airlines Logo
8:50 pm - 4:22 pmCLE-SXM
18h 32m2 stops
American Airlines Logo
4:00 pm - 11:54 pmSXM-CLE
8h 54m1 stop
$491American Airlines
Find Deal
Sat, Nov 29 - Sat, Dec 6
American Airlines Logo
1:23 pm - 2:00 pmCLE-SXM
23h 37m1 stop
American Airlines Logo
4:00 pm - 11:54 pmSXM-CLE
8h 54m1 stop
$494American Airlines
Find Deal
Sat, Nov 15 - Sun, Nov 23
United Airlines Logo
6:00 am - 1:50 pmCLE-SXM
6h 50m1 stop
United Airlines Logo
3:00 pm - 3:25 pmSXM-CLE
25h 25m1 stop
$518United Airlines
Find Deal
Wed, Feb 18 - Mon, Feb 23
Multiple Airlines Logo
6:15 pm - 2:40 pmCLE-SXM
19h 25m2 stops
Multiple Airlines Logo
4:28 pm - 11:20 amSXM-CLE
19h 52m1 stop
$524Multiple Airlines
Find Deal
Sat, Mar 7 - Wed, Mar 11
Air Canada Logo
6:15 pm - 1:40 pmCLE-SXM
18h 25m2 stops
Air Canada Logo
4:00 pm - 5:36 pmSXM-CLE
25h 36m1 stop
$550Air Canada
Find Deal
Thu, Oct 30 - Thu, Nov 6
United Airlines Logo
6:12 am - 12:50 pmCLE-SXM
6h 38m1 stop
United Airlines Logo
2:52 pm - 10:18 pmSXM-CLE
8h 26m1 stop
$609United Airlines
Find Deal
Wed, Nov 12 - Wed, Nov 19
Multiple Airlines Logo
2:55 pm - 3:21 pmCLE-SXM
23h 26m3 stops
Multiple Airlines Logo
4:28 pm - 12:21 pmSXM-CLE
20h 53m2 stops
$873Multiple Airlines
Find Deal

Everything you should know

Top airlines
American Airlines
Cheapest • from $461 (round-trip)
Delta
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to book
3 weeks
in advance
Our data shows that travelers who book at least 3 weeks in advance save around 37% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
November
Cheapest • 20% price drop
December
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Cheapest round-trip
$461
Typical prices: $485-587
American Airlines
Wed 11/12Wed 11/19
CLE - SXM • 1 stop
Cheapest one-way
$133
Frontier
Sat 12/6
CLE - SXM • 1 stop
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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!
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?

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 November, where tickets cost $511 (return) on average. On the other hand, the most expensive months are December and June, where the average cost of round-trip tickets is $775 and $760 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 3 weeks before departure, which saves you about 37% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 15 weeks before departure.

Good to know

Low seasonAugust
Cheapest flight$133
Best time to beat the crowds with an average 5% drop in price.
Most popular time to fly with an average 21% 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 3 days, the lowest price for a flight from Cleveland to Simpson Bay was $133 for a one-way ticket and $461 for a round-trip.

  • 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?

    oneworld, and Star Alliance 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 $619 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 $635 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 7954 reviews
7.9Entertainment
8.2Boarding
7.9Comfort
8.5Crew
7.3Food
Airline reviews

Passengers need to check in big baggage instead of bringing on the plane. That cause inconvenience for everyone. Otherwise flight was good.

8.0 ExcellentTarun, Sep 2025MCO - LHR
Read more Delta reviews

Passengers need to check in big baggage instead of bringing on the plane. That cause inconvenience for everyone. Otherwise flight was good.

Perfect flight both ways. On time, courteous staff, plane comfortable and cool. Best domestic flights I’ve had in awhile.

The food was terrible especially for a 15 hour international flight. The crew was unpleasant as well.

Really low quality food especially for an international flight. The crew also was surprisingly unpleasant except couple of ladies. I know we were not in first class but that’s no reason to treat customers as less.

Flight delayed for two and half hours and then canceled altogether due to mechanical issues. No mechanic onsite to fix so had to send one from LAX.

Quick check in. Everything went smooth. I don't know what can be done about airline food.

Crew was good. The reservation got mixed up and they didn't have my TSA number. I am also a Silver Medallion and wasn't able to use Sky Priority.

Delta made it easy, comfortable and timely. The crew was fantastic.

This route with Delta always has delays or is cancelled. Aircrafts seem smaller and older. I fly Delta quite a bit - haven’t had issues with the international flights. But this route has always been the troublesome one

Nothing special. The crew never went out of their way for anything.

We had to deboard 2 times due to maintenance issues. They changed the plane, and then we got deviated to LAX due to maibtenance issues on the other plane, had to sleep at LAX and los a full day.

Everything was good, except the seats in economy were so close together, you could barely get out when the seat in front of your was reclined. If the airlines keep jamming in more and more seats, it will become intolerable. I will look for another airline that considers customer comfort and does not keep adding more rows of seats for more profit.

The newer screen was super cool and had the option to watch many different shows or movies. Crew was polite and helpful. However again, many children screaming bloody murder and kicking my seat, and parents doing nothing about it as usual.

Flight was good and crew was super polite. However, there were around 5 kids screaming the WHOLE 2 hours. I understand kids have to come but parents need to do something to control their children. They make the experience terrible, especially after finishing 16 hour shifts at the hospital I needed some sleep, which I did not get.

IAD with the archaic people movers is just a place to be avoided.

Great service on board. Boarding a bit slow due to process. Food was pretty average.

Tastless food and too obvious lack of enthusiasm for service in the economy vesus business class

All of the United employees I interacted with were professional and courteous. The aircraft was clean, the food on the flight was good. No complaints here.

I had no checked baggage but was required to hand over carry on baggage at the door of the plane. There was a lot of overboard space in the plane and I was one of the last ones. I ran to get my carry on but it was gone. I was given back at the plane door in Toronto, so the wait was not as long as it would have been at the carousel.

Armrest controller on my seat 35D and nextbooennseat 35E did not work right. Hard to press buttons to recognize and 35D had constantnpressure either upmost down somit was nearly impossible to make selections. .

Given it’s a red-eye into Charolotte, we didn’t get any food. The survey does not include “N/A” so the rating will be skewed.

Great. Quick and quiet and east. The breakfast choices were a welcome surprise!

American airlines suck they delay the flights all the time made me sleep in an airport because my flight was delayed and I miss my connecting flight

There's nothing I liked about it. For first off I scheduled this trip two weeks in advance then they delayed my flight which messed up my whole trip. So I scheduled it for the following weekend thinking there won't be a delay and guess what as soon as I got to the airport we said in the airplane on the tarmac for an hour and a half. Not only was it delayed I missed my connecting flight meaning I had to stay the night at Dallas-Fort Worth airport sleeping on the floor. I will tell you this I will never fly American airlines ever again I have had nothing but horrible experience with them and I just throw money at them

The stewardess hit me with the food kart twice on the head and didn't say I'm sorry once. The same stewardess gave me a warm Apple Juice with No ice. The Flight was delayed for Departure 6 times, starting from 2:36pm, finally taking off 7:50pm. I was late picking up my child from the sitter by 3 hours.

Don’t know they cancelled the flight day before I was to leave. They sent a email at 9:00 pm at night saying they cancelled. That is the smooth way to say we don’t want your business! I think they didn’t have enough people booking so they cancelled the flight! It’s all about the money anymore there is no honesty in business.

Having to reschedule flights a day later, they loaded by luggage on the wrong plane from Little rock now I have to HOPE they deliver it to where im staying like they said would. International flight crew was very disgruntled and not very friendly.

We will be writing a long, detailed letter to corporate about our awful experience with American airlines.

It took way too long to diagnose and solve the problem of a broken crew member cabin seat. Though compensation for the volunteer who left the flight was very kind.

The entertainment package was vast and the selections were very current. Keep updating it was great.

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

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