$402+ Cheap flights from Cleveland (CLE) to Simpson Bay (SXM)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/22. Fares are subject to change and may not be available on all flights or dates of travel.
CLE — SXM
Nov 20 — Nov 271
Round-trip
1 adult, Economy
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Find cheap flights from Cleveland to Simpson Bay with Cheapflights
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Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Cheapest flights from Cleveland to Simpson BayExplore the most affordable flight options available from Cleveland to Simpson Bay. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 21, 2026.
Explore the most affordable flight options available from Cleveland to Simpson Bay. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 21, 2026.
This Air Canada deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2210:00 am -
1 stop7h 00m
Fri 10/303:45 pm -
1 stop26h 32m
Deal found 10/16![Air Canada logo]()
$402
This Air Canada deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/26:55 pm -
2 stops18h 50m
Mon 12/144:45 pm -
1 stop26h 34m
Deal found 10/18![Air Canada logo]()
$404
This Booking.com deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/36:55 pm -
1 stop19h 50m
Thu 12/103:45 pm -
2 stops27h 34m
Deal found 10/19![Air Canada logo]()
$453
This Air Canada deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/297:00 pm -
1 stop19h 45m
Thu 12/33:45 pm -
2 stops27h 34m
Deal found 10/19![Air Canada logo]()
$454
This Booking.com deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/76:55 pm -
1 stop19h 50m
Thu 12/103:45 pm -
2 stops27h 34m
Deal found 10/21![Air Canada logo]()
$473
This American Airlines deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/145:15 am -
1 stop9h 05m
Sat 11/213:26 pm -
1 stop8h 18m
Deal found 10/21![American Airlines logo]()
$485
Best flights from Cleveland to Simpson BayDiscover carefully curated flight deals from Cleveland to Simpson Bay that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 21, 2026.
Discover carefully curated flight deals from Cleveland to Simpson Bay that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 21, 2026.
This Air Canada deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/297:00 pm -
1 stop19h 45m
Thu 12/33:30 pm -
2 stops27h 49m
Deal found 10/20![Air Canada logo]()
$474
This United Airlines deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/167:35 pm -
1 stop19h 22m
Wed 12/235:00 pm -
1 stop7h 59m
Deal found 10/20![United Airlines logo]()
$494
This American Airlines deal was found by Cheapflights users on 10/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/207:58 pm -
2 stops17h 23m
Sat 2/275:42 pm -
2 stops18h 03m
Deal found 10/17![American Airlines logo]()
$499
This United Airlines deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/266:00 am -
1 stop6h 50m
Thu 3/44:55 pm -
1 stop7h 26m
Deal found 10/21![United Airlines logo]()
$494
This American Airlines deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/96:37 pm -
1 stop19h 22m
Sat 1/163:57 pm -
1 stop18h 35m
Deal found 10/19![American Airlines logo]()
$500
This American Airlines deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/296:00 am -
1 stop7h 21m
Sun 4/44:01 pm -
1 stop25h 23m
Deal found 10/19![American Airlines logo]()
$507
This United Airlines deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/56:00 am -
1 stop6h 50m
Sat 12/125:00 pm -
1 stop17h 38m
Deal found 10/21![United Airlines logo]()
$515
This United Airlines deal was found by Cheapflights users on 10/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/207:51 pm -
1 stop16h 59m
Sat 2/272:10 pm -
1 stop8h 59m
Deal found 10/17![United Airlines logo]()
$562
This American Airlines deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/135:20 pm -
2 stops18h 07m
Sun 2/215:22 pm -
1 stop25h 13m
Deal found 10/16![American Airlines logo]()
$649
This United Airlines deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/196:00 am -
1 stop6h 50m
Sun 2/285:00 pm -
1 stop17h 27m
Deal found 10/18![United Airlines logo]()
$608
This United Airlines deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/77:00 am -
1 stop7h 57m
Wed 11/112:52 pm -
1 stop22h 56m
Deal found 10/21![United Airlines logo]()
$674
Last-minute flights from Cleveland to Simpson BayDiscover last-minute flight deals from Cleveland to Simpson Bay. Data last updated October 21, 2026 and is based on user searches.
Discover last-minute flight deals from Cleveland to Simpson Bay. Data last updated October 21, 2026 and is based on user searches.
This Air Canada deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2210:00 am -
1 stop7h 00m
Fri 10/303:45 pm -
1 stop26h 32m
Deal found 10/16![Air Canada logo]()
$402
This American Airlines deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/76:55 pm -
2 stops18h 31m
Wed 11/115:33 pm -
2 stops16h 58m
Deal found 10/21![American Airlines logo]()
$541
This American Airlines deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/145:15 am -
1 stop9h 05m
Sat 11/213:26 pm -
1 stop8h 18m
Deal found 10/21![American Airlines logo]()
$485
This American Airlines deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/268:32 am -
2 stops28h 25m
Sat 12/54:30 pm -
2 stops19h 18m
Deal found 10/21![American Airlines logo]()
$504
This Air Canada deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/297:00 pm -
1 stop19h 45m
Thu 12/33:45 pm -
2 stops27h 34m
Deal found 10/19![Air Canada logo]()
$454
Find flight deals from Cleveland to Simpson Bay
Discover tips and strategies to find the most affordable flight options for your journey from Cleveland (CLE) to Simpson Bay (SXM). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated October 21, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $404 (Air Canada) |
Popular in | November |
Cheapest in | April |
Average price | $578 |
Cheapflights Fare Finder
Customize your flight search to find flights from Cleveland to Simpson Bay that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated October 21, 2026.
Use the filters below to find and compare flights from Cleveland to Simpson Bay that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ClevelandSimpson Bay
CLE Cleveland Hopkins Intl - SXM Simpson Bay Princess Juliana
CLESXM
Cleveland Hopkins Intl
Sun 11/29
7:00 pm-3:45 pm
1 stop19h 45m
Simpson Bay Princess Juliana
Thu 12/3
3:30 pm-6:19 pm
2 stops27h 49m
$474
ClevelandSimpson Bay
CLE Cleveland Hopkins Intl - SXM Simpson Bay Princess Juliana
CLESXM
Cleveland Hopkins Intl
Wed 12/16
7:35 pm-3:57 pm
1 stop19h 22m
Simpson Bay Princess Juliana
Wed 12/23
5:00 pm-11:59 pm
1 stop7h 59m
$494
Quickest round-trip
ClevelandSimpson Bay
CLE Cleveland Hopkins Intl - SXM Simpson Bay Princess Juliana
CLESXM
Cleveland Hopkins Intl
Fri 2/26
6:00 am-1:50 pm
1 stop6h 50m
Simpson Bay Princess Juliana
Thu 3/4
4:55 pm-11:21 pm
1 stop7h 26m
$494
ClevelandSimpson Bay
CLE Cleveland Hopkins Intl - SXM Simpson Bay Princess Juliana
CLESXM
Cleveland Hopkins Intl
Sat 2/20
7:58 pm-2:21 pm
2 stops17h 23m
Simpson Bay Princess Juliana
Sat 2/27
5:42 pm-10:45 am
2 stops18h 03m
$499
ClevelandSimpson Bay
CLE Cleveland Hopkins Intl - SXM Simpson Bay Princess Juliana
CLESXM
Cleveland Hopkins Intl
Sat 1/9
6:37 pm-2:59 pm
1 stop19h 22m
Simpson Bay Princess Juliana
Sat 1/16
3:57 pm-9:32 am
1 stop18h 35m
$500
ClevelandSimpson Bay
CLE Cleveland Hopkins Intl - SXM Simpson Bay Princess Juliana
CLESXM
Cleveland Hopkins Intl
Mon 3/29
6:00 am-1:21 pm
1 stop7h 21m
Simpson Bay Princess Juliana
Sun 4/4
4:01 pm-5:24 pm
1 stop25h 23m
$507
ClevelandSimpson Bay
CLE Cleveland Hopkins Intl - SXM Simpson Bay Princess Juliana
CLESXM
Cleveland Hopkins Intl
Sat 12/5
6:00 am-1:50 pm
1 stop6h 50m
Simpson Bay Princess Juliana
Sat 12/12
5:00 pm-9:38 am
1 stop17h 38m
$515
ClevelandSimpson Bay
CLE Cleveland Hopkins Intl - SXM Simpson Bay Princess Juliana
CLESXM
Cleveland Hopkins Intl
Sat 2/20
7:51 pm-1:50 pm
1 stop16h 59m
Simpson Bay Princess Juliana
Sat 2/27
2:10 pm-10:09 pm
1 stop8h 59m
$562
ClevelandSimpson Bay
CLE Cleveland Hopkins Intl - SXM Simpson Bay Princess Juliana
CLESXM
Cleveland Hopkins Intl
Fri 2/19
6:00 am-1:50 pm
1 stop6h 50m
Simpson Bay Princess Juliana
Sun 2/28
5:00 pm-9:27 am
1 stop17h 27m
$608
ClevelandSimpson Bay
CLE Cleveland Hopkins Intl - SXM Simpson Bay Princess Juliana
CLESXM
Cleveland Hopkins Intl
Sat 2/13
5:20 pm-12:27 pm
2 stops18h 07m
Simpson Bay Princess Juliana
Sun 2/21
5:22 pm-5:35 pm
1 stop25h 13m
$649
Showing 1-10 of 11 resultsSorted by cheapest first
Compare providers for flights from Cleveland to Simpson Bay
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Cleveland to Simpson Bay in October.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Cleveland-Simpson Bay flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Cleveland-Simpson Bay flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Cleveland-Simpson Bay flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Cleveland-Simpson Bay flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Cleveland-Simpson Bay flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Cleveland to Simpson Bay
Have a flexible travel schedule? Discover the best time to fly to Simpson Bay from Cleveland with our price prediction graph.
CLE-SXM
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Cleveland to Simpson Bay
What is the cheapest month to book a flight from Cleveland to Simpson Bay?
Currently, April is the cheapest month in which you can book a flight from Cleveland to Simpson Bay (average of $499). Flying from Cleveland to Simpson Bay in November is currently the most expensive (average of $754). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
How much does it cost to fly round-trip from Cleveland to Simpson Bay?
Airfare is below average for this route at the moment.
Cleveland to Simpson Bay flights typically cost between $598 and $712 in December.The cheapest round-trip price found within the last 5 days was $404 on Air Canada (Dec 2-Dec 14).
Reviews of airlines servicing Simpson Bay
Get insights into the airlines that provide service to Simpson Bay. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Simpson Bay. Reviews last updated October 21, 2026.
Peruse reviews from past customers who have flown with Delta,United Airlines, andJetBlue from Cleveland to Simpson Bay to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Food
7.2
Boarding
8.1
Entertainment
7.8
Overall
7.8
Crew
8.5
Comfort
7.8
Reviews
1 / 20
6.0
GoodEllen,Oct 2026
GRR - ATL
Food
7.2
Boarding
8.1
Entertainment
7.8
Overall
7.8
Crew
8.5
Comfort
7.8
Reviews
1 / 20
6.0
GoodEllen,Oct 2026
GRR - ATL
Food
7.2
Boarding
8.1
Entertainment
7.8
Overall
7.8
Crew
8.5
Comfort
7.8
Reviews
1 / 20
6.0
GoodEllen,Oct 2026
GRR - ATL
Food
7.2
Boarding
8.1
Entertainment
7.8
Overall
7.8
Crew
8.5
Comfort
7.8
Reviews
1 / 20
6.0
GoodEllen,Oct 2026
GRR - ATL
Food
7.2
Boarding
8.1
Entertainment
7.8
Overall
7.8
Crew
8.5
Comfort
7.8
Reviews
1 / 20
6.0
GoodEllen,Oct 2026
GRR - ATL
Related info for your journey
Find useful and relevant information for your journey from Cleveland to Simpson Bay. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Simpson Bay?
Book flights to Simpson Bay if you plan to visit one of these locationsPhilipsburg
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Cleveland and Simpson Bay flights
Browse other Cleveland and Simpson Bay flight options. Last updated on October 21, 2026.
Other flights from Cleveland
Browse through other flights departing from Cleveland. Flights are based on user searches made on Cheapflights and were last updated on October 21, 2026.
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Other flights to Simpson Bay
Explore flights to Simpson Bay departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on October 21, 2026.
Top 4 airlines flying from Cleveland to Simpson Bay
Discover the top 4 airlines that operate flights from Cleveland to Simpson Bay. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated October 21, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$202 | Average$681 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$276 | Average$486 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$435 | Average$678 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$447 | Average$628 | FlexibilityNo cancel fee | On-time69% |