$350+ 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 11/7. Fares are subject to change and may not be available on all flights or dates of travel.
CLE — SXM
Nov 6 — Nov 131
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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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 October 7, 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 7, 2026.
This American Airlines deal was found by Cheapflights users on 10/6. 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 11/113:26 pm -
1 stop8h 29m
Deal found 10/6![American Airlines logo]()
$350
This American Airlines deal was found by Cheapflights users on 10/5. 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 stop7h 15m
Wed 12/25:33 pm -
2 stops17h 02m
Deal found 10/5![American Airlines logo]()
$387
This American Airlines deal was found by Cheapflights users on 10/5. 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.
Mon 10/266:00 am -
1 stop9h 39m
Mon 11/22:26 pm -
1 stop10h 21m
Deal found 10/5![American Airlines logo]()
$396
This American Airlines deal was found by Cheapflights users on 10/6. 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 11/146:55 pm -
2 stops18h 31m
Sat 11/211:44 pm -
1 stop11h 55m
Deal found 10/6![American Airlines logo]()
$401
This Air Canada deal was found by Cheapflights users on 10/5. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/226:55 pm -
1 stop19h 50m
Tue 12/14:45 pm -
1 stop26h 34m
Deal found 10/5![Air Canada logo]()
$411
This American Airlines deal was found by Cheapflights users on 10/5. 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 10/286:00 am -
1 stop7h 23m
Fri 11/63:26 pm -
1 stop8h 29m
Deal found 10/5![American Airlines logo]()
$450
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 7, 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 7, 2026.
This American Airlines deal was found by Cheapflights users on 10/7. 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 -
2 stops16h 57m
Sat 1/163:04 pm -
1 stop9h 34m
Deal found 10/7![American Airlines logo]()
$428
This Delta deal was found by Cheapflights users on 10/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/306:00 am -
1 stop7h 40m
Fri 11/64:05 pm -
1 stop9h 52m
Deal found 10/2![Delta logo]()
$447
This United Airlines deal was found by Cheapflights users on 10/2. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/97:43 pm -
1 stop17h 07m
Sat 1/165:00 pm -
1 stop17h 47m
Deal found 10/2![United Airlines logo]()
$455
This American Airlines deal was found by Cheapflights users on 10/3. 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 11/145:15 am -
1 stop9h 05m
Sat 11/211:44 pm -
1 stop9h 35m
Deal found 10/3![American Airlines logo]()
$447
This American Airlines deal was found by Cheapflights users on 10/2. 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.
Mon 10/266:00 am -
1 stop9h 39m
Mon 11/25:33 pm -
2 stops16h 59m
Deal found 10/2![American Airlines logo]()
$452
This Delta deal was found by Cheapflights users on 10/5. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/237:05 am -
1 stop6h 35m
Wed 12/24:05 pm -
1 stop10h 02m
Deal found 10/5![Delta logo]()
$519
This American Airlines deal was found by Cheapflights users on 10/4. 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 11/113:26 pm -
1 stop8h 29m
Deal found 10/4![American Airlines logo]()
$452
This American Airlines deal was found by Cheapflights users on 10/4. 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 11/267:32 am -
2 stops29h 25m
Sat 12/55:33 pm -
2 stops18h 15m
Deal found 10/4![American Airlines logo]()
$466
This American Airlines deal was found by Cheapflights users on 10/6. 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 10/285:00 am -
2 stops10h 39m
Fri 11/65:33 pm -
2 stops19h 01m
Deal found 10/6![American Airlines logo]()
$475
This American Airlines deal was found by Cheapflights users on 10/7. 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 12/308:37 pm -
2 stops18h 53m
Wed 1/64:02 pm -
1 stop8h 37m
Deal found 10/7![American Airlines logo]()
$533
Last-minute flights from Cleveland to Simpson BayDiscover last-minute flight deals from Cleveland to Simpson Bay. Data last updated October 7, 2026 and is based on user searches.
Discover last-minute flight deals from Cleveland to Simpson Bay. Data last updated October 7, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 10/5. 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.
Mon 10/266:00 am -
1 stop9h 39m
Mon 11/22:26 pm -
1 stop10h 21m
Deal found 10/5![American Airlines logo]()
$396
This American Airlines deal was found by Cheapflights users on 10/5. 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 10/286:00 am -
1 stop7h 23m
Fri 11/63:26 pm -
1 stop8h 29m
Deal found 10/5![American Airlines logo]()
$450
This American Airlines deal was found by Cheapflights users on 10/6. 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 11/113:26 pm -
1 stop8h 29m
Deal found 10/6![American Airlines logo]()
$350
This American Airlines deal was found by Cheapflights users on 10/6. 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 11/146:55 pm -
2 stops18h 31m
Sat 11/211:44 pm -
1 stop11h 55m
Deal found 10/6![American Airlines logo]()
$401
This Air Canada deal was found by Cheapflights users on 10/5. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/226:55 pm -
1 stop19h 50m
Tue 12/14:45 pm -
1 stop26h 34m
Deal found 10/5![Air Canada logo]()
$411
This American Airlines deal was found by Cheapflights users on 10/5. 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 stop7h 15m
Wed 12/25:33 pm -
2 stops17h 02m
Deal found 10/5![American Airlines logo]()
$387
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 7, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $350 (American Airlines) |
Popular in | November |
Cheapest in | April |
Average price | $511 |
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 7, 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
Sat 1/9
6:37 pm-12:34 pm
2 stops16h 57m
Simpson Bay Princess Juliana
Sat 1/16
3:04 pm-11:38 pm
1 stop9h 34m
$428
ClevelandSimpson Bay
CLE Cleveland Hopkins Intl - SXM Simpson Bay Princess Juliana
CLESXM
Cleveland Hopkins Intl
Fri 10/30
6:00 am-1:40 pm
1 stop7h 40m
Simpson Bay Princess Juliana
Fri 11/6
4:05 pm-12:57 am
1 stop9h 52m
$447
ClevelandSimpson Bay
CLE Cleveland Hopkins Intl - SXM Simpson Bay Princess Juliana
CLESXM
Cleveland Hopkins Intl
Sat 11/14
5:15 am-3:20 pm
1 stop9h 05m
Simpson Bay Princess Juliana
Sat 11/21
1:44 pm-10:19 pm
1 stop9h 35m
$447
ClevelandSimpson Bay
CLE Cleveland Hopkins Intl - SXM Simpson Bay Princess Juliana
CLESXM
Cleveland Hopkins Intl
Mon 10/26
6:00 am-3:39 pm
1 stop9h 39m
Simpson Bay Princess Juliana
Mon 11/2
5:33 pm-9:32 am
2 stops16h 59m
$452
ClevelandSimpson Bay
CLE Cleveland Hopkins Intl - SXM Simpson Bay Princess Juliana
CLESXM
Cleveland Hopkins Intl
Sat 11/7
6:52 pm-2:26 pm
2 stops18h 34m
Simpson Bay Princess Juliana
Wed 11/11
3:26 pm-10:55 pm
1 stop8h 29m
$452
ClevelandSimpson Bay
CLE Cleveland Hopkins Intl - SXM Simpson Bay Princess Juliana
CLESXM
Cleveland Hopkins Intl
Sat 1/9
7:43 pm-1:50 pm
1 stop17h 07m
Simpson Bay Princess Juliana
Sat 1/16
5:00 pm-9:47 am
1 stop17h 47m
$455
ClevelandSimpson Bay
CLE Cleveland Hopkins Intl - SXM Simpson Bay Princess Juliana
CLESXM
Cleveland Hopkins Intl
Thu 11/26
7:32 am-1:57 pm
2 stops29h 25m
Simpson Bay Princess Juliana
Sat 12/5
5:33 pm-10:48 am
2 stops18h 15m
$466
ClevelandSimpson Bay
CLE Cleveland Hopkins Intl - SXM Simpson Bay Princess Juliana
CLESXM
Cleveland Hopkins Intl
Wed 10/28
5:00 am-3:39 pm
2 stops10h 39m
Simpson Bay Princess Juliana
Fri 11/6
5:33 pm-11:34 am
2 stops19h 01m
$475
Quickest round-trip
ClevelandSimpson Bay
CLE Cleveland Hopkins Intl - SXM Simpson Bay Princess Juliana
CLESXM
Cleveland Hopkins Intl
Mon 11/23
7:05 am-2:40 pm
1 stop6h 35m
Simpson Bay Princess Juliana
Wed 12/2
4:05 pm-1:07 am
1 stop10h 02m
$519
ClevelandSimpson Bay
CLE Cleveland Hopkins Intl - SXM Simpson Bay Princess Juliana
CLESXM
Cleveland Hopkins Intl
Wed 12/30
8:37 pm-4:30 pm
2 stops18h 53m
Simpson Bay Princess Juliana
Wed 1/6
4:02 pm-11:39 pm
1 stop8h 37m
$533
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 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
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 October 7, 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.
Entertainment
7.8
Comfort
7.8
Crew
8.5
Boarding
8.1
Food
7.2
Overall
7.8
Reviews
1 / 20
4.0
OkayJennifer,Sep 2026
ORD - LGA
Entertainment
7.8
Comfort
7.8
Crew
8.5
Boarding
8.1
Food
7.2
Overall
7.8
Reviews
1 / 20
4.0
OkayJennifer,Sep 2026
ORD - LGA
Entertainment
7.8
Comfort
7.8
Crew
8.5
Boarding
8.1
Food
7.2
Overall
7.8
Reviews
1 / 20
4.0
OkayJennifer,Sep 2026
ORD - LGA
Entertainment
7.8
Comfort
7.8
Crew
8.5
Boarding
8.1
Food
7.2
Overall
7.8
Reviews
1 / 20
4.0
OkayJennifer,Sep 2026
ORD - LGA
Entertainment
7.8
Comfort
7.8
Crew
8.5
Boarding
8.1
Food
7.2
Overall
7.8
Reviews
1 / 20
4.0
OkayJennifer,Sep 2026
ORD - LGA
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 7, 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 7, 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 7, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$202 | Average$691 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$276 | Average$486 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$435 | Average$672 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$447 | Average$708 | FlexibilityNo cancel fee | On-time69% |