$374+ 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 11/26. Fares are subject to change and may not be available on all flights or dates of travel.
CLE — SXM
Oct 6 — Oct 131
Round-trip
1 adult, Economy
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Find cheap flights from Cleveland to Simpson Bay with Cheapflights
1. Tell us where you want to go
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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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Cleveland to Simpson Bay
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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 September 6, 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 September 6, 2026.
This Air Canada deal was found by Cheapflights users on 9/3. 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 11/266:55 pm -
1 stop19h 50m
Sat 12/53:45 pm -
2 stops27h 34m
Deal found 9/3![Air Canada logo]()
$374
This Expedia deal was found by Cheapflights users on 9/1. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/2410:00 am -
1 stop28h 45m
Mon 10/263:45 pm -
1 stop26h 32m
Deal found 9/1![Air Canada logo]()
$409
This American Airlines deal was found by Cheapflights users on 9/2. 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 11/76:52 pm -
2 stops18h 34m
Wed 11/115:33 pm -
2 stops19h 32m
Deal found 9/2![American Airlines logo]()
$412
This American Airlines deal was found by Cheapflights users on 9/1. 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.
Fri 10/167:38 pm -
2 stops20h 01m
Fri 10/234:39 pm -
2 stops18h 52m
Deal found 9/1![American Airlines logo]()
$415
This American Airlines deal was found by Cheapflights users on 9/2. 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.
Tue 11/176:00 am -
2 stops9h 31m
Sun 11/225:29 pm -
2 stops18h 57m
Deal found 9/2![American Airlines logo]()
$417
This American Airlines deal was found by Cheapflights users on 9/1. 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.
Wed 11/118:59 pm -
2 stops18h 32m
Sun 11/155:33 pm -
2 stops19h 32m
Deal found 9/1![American Airlines logo]()
$422
This American Airlines deal was found by Cheapflights users on 9/2. 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 11/2610:13 am -
2 stops26h 44m
Sat 12/55:33 pm -
2 stops20h 37m
Deal found 9/2![American Airlines logo]()
$425
This American Airlines deal was found by Cheapflights users on 9/2. 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 11/56:55 pm -
1 stop18h 31m
Sun 11/85:33 pm -
2 stops19h 32m
Deal found 9/2![American Airlines logo]()
$426
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 September 6, 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 September 6, 2026.
This Expedia deal was found by Cheapflights users on 9/1. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/106:55 pm -
1 stop19h 50m
Sun 12/134:45 pm -
1 stop26h 34m
Deal found 9/1![Air Canada logo]()
$409
This American Airlines deal was found by Cheapflights users on 9/1. 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.
Fri 10/167:38 pm -
2 stops20h 01m
Fri 10/234:39 pm -
2 stops18h 52m
Deal found 9/1![American Airlines logo]()
$415
This Justfly.com deal was found by Cheapflights users on 9/5. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/76:55 pm -
1 stop19h 50m
Wed 11/112:09 pm -
1 stop10h 50m
Deal found 9/5![Multiple Airlines logo]()
$495
This Justfly.com deal was found by Cheapflights users on 9/5. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/266:55 pm -
1 stop19h 50m
Sat 12/53:45 pm -
2 stops27h 34m
Deal found 9/5![Air Canada logo]()
$415
This American Airlines deal was found by Cheapflights users on 9/2. 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.
Tue 1/265:05 am -
2 stops10h 28m
Sun 1/315:33 pm -
2 stops16h 51m
Deal found 9/2![American Airlines logo]()
$424
This American Airlines deal was found by Cheapflights users on 9/3. 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 11/76:52 pm -
2 stops20h 39m
Wed 11/113:26 pm -
1 stop8h 29m
Deal found 9/3![American Airlines logo]()
$432
This American Airlines deal was found by Cheapflights users on 9/5. 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 11/266:00 am -
1 stop9h 24m
Sat 12/52:55 pm -
1 stop20h 48m
Deal found 9/5![American Airlines logo]()
$434
This American Airlines deal was found by Cheapflights users on 9/3. 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 1/98:37 pm -
2 stops18h 56m
Sat 1/161:01 pm -
1 stop11h 37m
Deal found 9/3![American Airlines logo]()
$439
This American Airlines deal was found by Cheapflights users on 9/2. 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 11/55:08 pm -
2 stops20h 18m
Sun 11/85:33 pm -
2 stops19h 32m
Deal found 9/2![American Airlines logo]()
$447
Last-minute flights from Cleveland to Simpson BayDiscover last-minute flight deals from Cleveland to Simpson Bay. Data last updated September 6, 2026 and is based on user searches.
Discover last-minute flight deals from Cleveland to Simpson Bay. Data last updated September 6, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 9/2. 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.
Wed 10/76:05 am -
2 stops9h 34m
Mon 10/124:39 pm -
2 stops21h 35m
Deal found 9/2![American Airlines logo]()
$450
This American Airlines deal was found by Cheapflights users on 9/2. 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.
Wed 10/76:05 am -
2 stops9h 34m
Sun 10/114:39 pm -
2 stops20h 20m
Deal found 9/2![American Airlines logo]()
$455
This Travelocity deal was found by Cheapflights users on 9/2. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/77:00 pm -
1 stop22h 00m
Sun 10/111:48 pm -
1 stop10h 11m
Deal found 9/2![Multiple Airlines logo]()
$510
This American Airlines deal was found by Cheapflights users on 9/2. 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 10/85:25 pm -
2 stops22h 14m
Mon 10/124:39 pm -
2 stops24h 06m
Deal found 9/2![American Airlines logo]()
$512
This Priceline deal was found by Cheapflights users on 9/1. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/97:00 pm -
1 stop22h 00m
Sun 10/111:48 pm -
1 stop10h 11m
Deal found 9/1![Multiple Airlines logo]()
$505
This American Airlines deal was found by Cheapflights users on 9/5. 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.
Wed 10/145:00 am -
2 stops10h 39m
Sun 10/184:39 pm -
2 stops20h 33m
Deal found 9/5![American Airlines logo]()
$448
This American Airlines deal was found by Cheapflights users on 9/3. 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 10/157:38 pm -
2 stops17h 45m
Mon 10/194:39 pm -
2 stops18h 49m
Deal found 9/3![American Airlines logo]()
$438
This American Airlines deal was found by Cheapflights users on 9/3. 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 10/157:38 pm -
2 stops20h 01m
Sun 10/184:39 pm -
2 stops20h 33m
Deal found 9/3![American Airlines logo]()
$443
This American Airlines deal was found by Cheapflights users on 9/1. 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.
Fri 10/167:38 pm -
2 stops20h 01m
Fri 10/234:39 pm -
2 stops18h 52m
Deal found 9/1![American Airlines logo]()
$415
This Expedia deal was found by Cheapflights users on 9/1. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/2410:00 am -
1 stop28h 45m
Mon 10/263:45 pm -
1 stop26h 32m
Deal found 9/1![Air Canada logo]()
$409
This American Airlines deal was found by Cheapflights users on 9/1. 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 10/244:28 pm -
2 stops20h 55m
Mon 10/264:39 pm -
2 stops17h 12m
Deal found 9/1![American Airlines logo]()
$412
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 September 6, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $374 (Air Canada) |
Popular in | November |
Cheapest in | April |
Average price | $588 |
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 September 6, 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
Thu 12/10
6:55 pm-3:45 pm
1 stop19h 50m
Simpson Bay Princess Juliana
Sun 12/13
4:45 pm-6:19 pm
1 stop26h 34m
$409
ClevelandSimpson Bay
CLE Cleveland Hopkins Intl - SXM Simpson Bay Princess Juliana
CLESXM
Cleveland Hopkins Intl
Fri 10/16
7:38 pm-3:39 pm
2 stops20h 01m
Simpson Bay Princess Juliana
Fri 10/23
4:39 pm-11:31 am
2 stops18h 52m
$415
ClevelandSimpson Bay
CLE Cleveland Hopkins Intl - SXM Simpson Bay Princess Juliana
CLESXM
Cleveland Hopkins Intl
Thu 11/26
6:55 pm-3:45 pm
1 stop19h 50m
Simpson Bay Princess Juliana
Sat 12/5
3:45 pm-6:19 pm
2 stops27h 34m
$415
Quickest round-trip
ClevelandSimpson Bay
CLE Cleveland Hopkins Intl - SXM Simpson Bay Princess Juliana
CLESXM
Cleveland Hopkins Intl
Tue 1/26
5:05 am-4:33 pm
2 stops10h 28m
Simpson Bay Princess Juliana
Sun 1/31
5:33 pm-9:24 am
2 stops16h 51m
$424
ClevelandSimpson Bay
CLE Cleveland Hopkins Intl - SXM Simpson Bay Princess Juliana
CLESXM
Cleveland Hopkins Intl
Sat 11/7
6:52 pm-4:31 pm
2 stops20h 39m
Simpson Bay Princess Juliana
Wed 11/11
3:26 pm-10:55 pm
1 stop8h 29m
$432
ClevelandSimpson Bay
CLE Cleveland Hopkins Intl - SXM Simpson Bay Princess Juliana
CLESXM
Cleveland Hopkins Intl
Thu 11/26
6:00 am-4:24 pm
1 stop9h 24m
Simpson Bay Princess Juliana
Sat 12/5
2:55 pm-10:43 am
1 stop20h 48m
$434
ClevelandSimpson Bay
CLE Cleveland Hopkins Intl - SXM Simpson Bay Princess Juliana
CLESXM
Cleveland Hopkins Intl
Sat 1/9
8:37 pm-4:33 pm
2 stops18h 56m
Simpson Bay Princess Juliana
Sat 1/16
1:01 pm-11:38 pm
1 stop11h 37m
$439
ClevelandSimpson Bay
CLE Cleveland Hopkins Intl - SXM Simpson Bay Princess Juliana
CLESXM
Cleveland Hopkins Intl
Thu 11/5
5:08 pm-2:26 pm
2 stops20h 18m
Simpson Bay Princess Juliana
Sun 11/8
5:33 pm-12:05 pm
2 stops19h 32m
$447
ClevelandSimpson Bay
CLE Cleveland Hopkins Intl - SXM Simpson Bay Princess Juliana
CLESXM
Cleveland Hopkins Intl
Sat 11/7
6:55 pm-3:45 pm
1 stop19h 50m
Simpson Bay Princess Juliana
Wed 11/11
2:09 pm-11:59 pm
1 stop10h 50m
$495
Sorted 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 September.
| 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
How far ahead should I book a flight from Cleveland to Simpson Bay?
The best time to book flights from Cleveland to Simpson Bay is 11 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
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 $749). 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.
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 September 6, 2026.
Peruse reviews from past customers who have flown with Delta,United Airlines, andAmerican Airlines 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
Overall
7.8
Crew
8.5
Boarding
8.1
Entertainment
7.8
Comfort
7.8
Reviews
1 / 20
8.0
ExcellentJorge,Aug 2026
TPA - ATL
Food
7.2
Overall
7.8
Crew
8.5
Boarding
8.1
Entertainment
7.8
Comfort
7.8
Reviews
1 / 20
8.0
ExcellentJorge,Aug 2026
TPA - ATL
Food
7.2
Overall
7.8
Crew
8.5
Boarding
8.1
Entertainment
7.8
Comfort
7.8
Reviews
1 / 20
8.0
ExcellentJorge,Aug 2026
TPA - ATL
Food
7.2
Overall
7.8
Crew
8.5
Boarding
8.1
Entertainment
7.8
Comfort
7.8
Reviews
1 / 20
8.0
ExcellentJorge,Aug 2026
TPA - ATL
Food
7.2
Overall
7.8
Crew
8.5
Boarding
8.1
Entertainment
7.8
Comfort
7.8
Reviews
1 / 20
8.0
ExcellentJorge,Aug 2026
TPA - 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 September 6, 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 September 6, 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 September 6, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$202 | Average$691 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$276 | Average$466 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$435 | Average$675 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$447 | Average$653 | FlexibilityNo cancel fee | On-time69% |