CLE - SXM

$133 Find Cheap Flights from Cleveland to Simpson Bay - Compare and Save

1 adult
1 adult, Economy, 0 bags

Save 21% or more on flights. Compare deals from all over the web.

Never overpay with our price tracking tools.

Filter searches by price, airline and more to find your best flights.

Everything you should know

Cheapest round-trip
$362
Typical prices: $534-$794
Air Canada
Mon 11/12Fri 11/23
CLE - SXM • 1 stop
Cheapest one-way
$133
Typical prices: $209-$268
Air Canada
Sat 12/15
CLE - SXM • 1 stop
Nonstop flights
Not available
There are currently no direct flights between Cleveland and Simpson Bay. You'll need to take a connecting flight to reach the destination.
Insights
Insights
When to book
12 weeks
in advance
Our data shows that travelers who book at least 12 weeks in advance save around 38% compared to booking last minute.
Insights
Insights
When to travel
April
Cheapest • 27% price drop
November
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Fort Lauderdale (FLL)
Cheapest • Avg $444 (round-trip)
Washington, D.C. Dulles Intl (IAD)
Shortest trip • 7h 13m (one-way)
Insights
Insights
Start a new search
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)

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Cleveland to Simpson Bay

Sat, Dec 5 - Thu, Dec 10
Air Canada Logo
6:55 pm - 3:45 pmCLE  Cleveland Hopkins Intl-SXM Simpson Bay Princess Juliana
19h 50m1 stop Toronto Pearson Intl
Air Canada Logo
3:45 pm - 6:19 pmSXM  Simpson Bay Princess Juliana-CLE Cleveland Hopkins Intl
27h 34m2 stops Montreal Pierre Elliott Trudeau Intl Toronto Pearson Intl
$352Air Canada
Sat, Nov 14 - Mon, Nov 23
Air Canada Logo
6:55 pm - 3:45 pmCLE  Cleveland Hopkins Intl-SXM Simpson Bay Princess Juliana
19h 50m1 stop Toronto Pearson Intl
Air Canada Logo
4:45 pm - 6:17 pmSXM  Simpson Bay Princess Juliana-CLE Cleveland Hopkins Intl
26h 32m1 stop Toronto Pearson Intl
$362Air Canada
Sat, Dec 5 - Thu, Dec 10
United Airlines Logo
7:00 am - 3:57 pmCLE  Cleveland Hopkins Intl-SXM Simpson Bay Princess Juliana
7h 57m1 stop Chicago O'Hare Intl
United Airlines Logo
2:52 pm - 8:25 amSXM  Simpson Bay Princess Juliana-CLE Cleveland Hopkins Intl
18h 33m1 stop Newark
$427United Airlines
Sat, Oct 24 - Sat, Oct 31
Delta Logo
6:00 am - 1:40 pmCLE  Cleveland Hopkins Intl-SXM Simpson Bay Princess Juliana
7h 40m1 stop Atlanta Hartsfield-Jackson
Delta Logo
3:05 pm - 12:57 amSXM  Simpson Bay Princess Juliana-CLE Cleveland Hopkins Intl
9h 52m1 stop Atlanta Hartsfield-Jackson
$430Delta
Sat, Dec 5 - Thu, Dec 10
American Airlines Logo
6:52 pm - 4:31 pmCLE  Cleveland Hopkins Intl-SXM Simpson Bay Princess Juliana
20h 39m2 stops Charlotte Douglas Miami
American Airlines Logo
5:33 pm - 7:48 amSXM  Simpson Bay Princess Juliana-CLE Cleveland Hopkins Intl
15h 15m2 stops Miami Washington, D.C. Reagan-National
$432American Airlines
Sat, Nov 7 - Wed, Nov 11
American Airlines Logo
6:52 pm - 2:26 pmCLE  Cleveland Hopkins Intl-SXM Simpson Bay Princess Juliana
18h 34m2 stops Charlotte Douglas Miami
American Airlines Logo
3:26 pm - 10:55 pmSXM  Simpson Bay Princess Juliana-CLE Cleveland Hopkins Intl
8h 29m1 stop Miami
$432American Airlines
Mon, Nov 16 - Tue, Nov 24
Delta Logo
7:05 am - 2:40 pmCLE  Cleveland Hopkins Intl-SXM Simpson Bay Princess Juliana
6h 35m1 stop Atlanta Hartsfield-Jackson
Delta Logo
4:05 pm - 12:57 amSXM  Simpson Bay Princess Juliana-CLE Cleveland Hopkins Intl
9h 52m1 stop Atlanta Hartsfield-Jackson
$447Delta
Sat, Nov 14 - Sat, Nov 21
United Airlines Logo
7:00 am - 3:57 pmCLE  Cleveland Hopkins Intl-SXM Simpson Bay Princess Juliana
7h 57m1 stop Chicago O'Hare Intl
United Airlines Logo
5:00 pm - 9:38 amSXM  Simpson Bay Princess Juliana-CLE Cleveland Hopkins Intl
17h 38m1 stop Washington, D.C. Dulles Intl
$460United Airlines
Tue, Dec 29 - Wed, Dec 30
JetBlue Logo
6:00 am - 3:11 pmCLE  Cleveland Hopkins Intl-SXM Simpson Bay Princess Juliana
8h 11m1 stop New York John F Kennedy Intl
JetBlue Logo
1:41 pm - 9:56 pmSXM  Simpson Bay Princess Juliana-CLE Cleveland Hopkins Intl
9h 15m1 stop Boston Logan Intl
$690JetBlue
Mon, Dec 28 - Wed, Dec 30
JetBlue Logo
6:00 am - 3:11 pmCLE  Cleveland Hopkins Intl-SXM Simpson Bay Princess Juliana
8h 11m1 stop New York John F Kennedy Intl
JetBlue Logo
1:41 pm - 9:56 pmSXM  Simpson Bay Princess Juliana-CLE Cleveland Hopkins Intl
9h 15m1 stop Boston Logan Intl
$996JetBlue
Booking Insights

Price, demand and travel trends for Cleveland to Simpson Bay flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights from Cleveland to Simpson Bay with more confidence.

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

Round-trip flights from Cleveland to Simpson Bay start at $362. Prices are below average for this route right now, with typical round-trip fares ranging from $534 to $794. The lowest price found in the past 5 days was $362 on Air Canada.

What's the cheapest day of the week to fly from Cleveland to Simpson Bay?

Tuesday is the cheapest day of the week to fly from Cleveland to Simpson Bay, it is 18% cheaper than the average day. Friday is the most expensive day with flight prices 9% higher than average. Based on deals found by KAYAK users in the last 12 months.

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

  • April is the cheapest month to fly from Cleveland to Simpson Bay at $499 round-trip.
  • November ($751) and December ($706) are the most expensive months.
  • The price difference between flying in the cheapest and most expensive months is 50% on average.
This is based on KAYAK aggregated and averaged internal data over the past 12 months.

When are prices from Cleveland to Simpson Bay the cheapest?

Flights from Cleveland to Simpson Bay are cheapest 12 weeks before departure. Booking in this window typically costs about 38% less than the average last-minute fare (within 2 weeks of the flight), based on KAYAK data.

Find deals

Key details for Cleveland to Simpson Bay flights

Low season

August

Cheapest flight

$133
Best time to beat the crowds with an average 10% drop in price.
Most popular time to fly with an average 9% 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

Your Cleveland to Simpson Bay flight questions, answered

Find helpful route details based on KAYAK data, including flight times, airports, airlines and booking questions.

  • Which airports can I use when flying from Cleveland to Simpson Bay?

    Flights from Cleveland to Simpson Bay usually depart from Cleveland Hopkins Intl (CLE) and arrive at Simpson Bay Princess Juliana (SXM).

  • What cabin classes can I book on flights from Cleveland to Simpson Bay?

    Two cabin classes are available on flights from Cleveland to Simpson Bay:

    • Economy Class
    • First Class

  • Which airports do connecting flights from Cleveland to Simpson Bay pass through?

    One-stop flights from Cleveland to Simpson Bay most commonly connect through:

    • Atlanta Hartsfield-Jackson (ATL) - 31% of one-stop connections
    • Charlotte Douglas (CLT) - 29% of one-stop connections
    • Miami (MIA) - 23% of one-stop connections
    • Washington, D.C. Dulles Intl (IAD) - 7% of one-stop connections

    Atlanta Hartsfield-Jackson (ATL) handles the largest share of one-stop connections on this route.

  • Can I save money by using flexible dates for flights from Cleveland to Simpson Bay?

    Yes. Being flexible with your travel dates can save you up to 25% on the Cleveland to Simpson Bay route. Tuesday is the cheapest departure day at $568 round-trip on average, while Friday is the most expensive at $749, a difference of $181. KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

  • How expensive are last-minute Cleveland to Simpson Bay flights?

    Last-minute fares on this route - booked within 2 weeks of departure - run 5% above the route average of $687. Book 12 weeks before departure for the lowest fares.

  • How long is a flight from Cleveland to Simpson Bay?

    A nonstop flight from Cleveland to Simpson Bay takes 0h 00m, covering 1,957 miles.

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

    Yes, a valid passport is required for this international route. Many destinations require at least six months of validity beyond your travel dates. Check your passport expiry well before booking.

  • How are flight prices from Cleveland to Simpson Bay looking right now?

    One-way fares from Cleveland to Simpson Bay are currently higher than usual. Average one-way flight prices are about $274, which is 7% above the typical average for this route.

  • How much time can I save by choosing a different layover airport from Cleveland to Simpson Bay?

    Flying via Washington, D.C. Dulles Intl (IAD) gives the shortest average 1-stop total travel time at 7h 13m, compared with 7h 26m via Philadelphia (PHL) and 7h 57m via Charlotte Douglas (CLT).

  • What car rental options are available at Simpson Bay Princess Juliana Airport (SXM)?

    Simpson Bay Princess Juliana Airport (SXM) hosts 5 major car rental companies, with daily rates starting from around $2 for economy cars. Top options include:
    • Ace
    • Right Cars
    • Europcar
    • Budget
    • Alamo

  • How much should I expect to pay for a Cleveland to Simpson Bay flight?

    Round-trip flights from Cleveland to Simpson Bay range from $534 to $794, with an average of $687 over the past 12 months. Anything below $534 counts as a good deal.

Your guide to booking Cleveland to Simpson Bay flights

Get tips on when to book, when to fly and what to know before your trip.
  • If your dates can be flexible, aim for a Tuesday departure instead of Friday. On this route, Tuesday flights average $568 - about $181 less than Friday (24% savings) based on the last 12 months.
  • For the best chance at a low fare, aim to book around 12 weeks before you fly. On this route, that window historically saves about 38% versus last-minute pricing (KAYAK booking data, last 12 months).
  • If you can choose when to travel, plan your Cleveland to Simpson Bay trip for April. Fares historically average $499 round-trip in that month - typically $252 less than the most expensive month, which is November (based on the last 12 months).
  • If you're arriving late at night and need somewhere to stay, check out these hotels close to Simpson Bay Princess Juliana Airport.
    - Hilton Vacation Club Flamingo Beach St. Maarten
    - Simpson Bay Resort Marina & Spa
    - The Atrium Beach Resort and Spa Sint Maarten, an Ascend Collection Hotel

More options for your flight from Cleveland to Simpson Bay

Complete your trip to Simpson Bay with a hotel stay or car rental

Car rentals in Simpson Bay
Hotels in Simpson Bay
Vacations in Simpson Bay