$202+ Cheap flights from Cleveland (CLE) to Simpson Bay (SXM)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 7/18. Fares are subject to change and may not be available on all flights or dates of travel.
CLE — SXM
Jul 12 — Jul 191
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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Best
Last-minute
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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 June 12, 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 June 12, 2026.
This Air Canada deal was found by Cheapflights users on 6/7. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/1310:10 am
CLE
- SXM
1 stop6h 50m
Air Canada
Sat 6/206:00 pm
SXM
- CLE
1 stop20h 05m
Air Canada
Deal found 6/7![Air Canada logo]()
$420
This Travelocity deal was found by Cheapflights users on 6/8. 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.
Sat 6/1310:10 am
CLE
- SXM
1 stop6h 50m
Multiple Airlines
Sat 6/2012:43 pm
SXM
- CLE
1 stop9h 52m
Multiple Airlines
Deal found 6/8![Multiple Airlines logo]()
$470
This Super.com deal was found by Cheapflights users on 6/8. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/306:25 am
CLE
- SXM
1 stop7h 17m
JetBlue
Thu 9/31:42 pm
SXM
- CLE
1 stop10h 17m
JetBlue
Deal found 6/8![JetBlue logo]()
$479
This American Airlines deal was found by Cheapflights users on 6/10. 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 8/36:01 am
CLE
- SXM
1 stop9h 43m
American Airlines
Thu 8/132:42 pm
SXM
- CLE
1 stop8h 56m
American Airlines
Deal found 6/10![American Airlines logo]()
$493
This Cheapflightsfares deal was found by Cheapflights users on 6/8. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/196:25 am
CLE
- SXM
1 stop7h 17m
JetBlue
Wed 8/261:42 pm
SXM
- CLE
1 stop10h 17m
JetBlue
Deal found 6/8![JetBlue logo]()
$496
This American Airlines deal was found by Cheapflights users on 6/9. 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 7/411:39 am
CLE
- SXM
1 stop26h 12m
American Airlines
Tue 7/72:51 pm
SXM
- CLE
1 stop9h 38m
American Airlines
Deal found 6/9![American Airlines logo]()
$501
This American Airlines deal was found by Cheapflights users on 6/8. 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.
Sun 8/96:15 am
CLE
- SXM
1 stop9h 24m
American Airlines
Sun 8/164:39 pm
SXM
- CLE
2 stops19h 07m
American Airlines
Deal found 6/8![American Airlines logo]()
$503
This American Airlines deal was found by Cheapflights users on 6/10. 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 11/261:23 pm
CLE
- SXM
1 stop23h 37m
American Airlines
Sat 12/55:25 pm
SXM
- CLE
2 stops18h 05m
American Airlines
Deal found 6/10![American Airlines logo]()
$505
This American Airlines deal was found by Cheapflights users on 6/10. 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 8/56:15 am
CLE
- SXM
1 stop9h 24m
American Airlines
Sun 8/92:22 pm
SXM
- CLE
2 stops19h 13m
American Airlines
Deal found 6/10![American Airlines logo]()
$508
This American Airlines deal was found by Cheapflights users on 6/11. 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 7/237:08 pm
CLE
- SXM
1 stop20h 36m
American Airlines
Mon 7/274:45 pm
SXM
- CLE
2 stops18h 27m
American Airlines
Deal found 6/11![American Airlines logo]()
$509
This United Airlines deal was found by Cheapflights users on 6/8. 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 7/186:00 am
CLE
- SXM
1 stop6h 33m
United Airlines
Sat 7/253:50 pm
SXM
- CLE
1 stop7h 54m
United Airlines
Deal found 6/8![United Airlines logo]()
$518
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 June 12, 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 June 12, 2026.
This American Airlines deal was found by Cheapflights users on 6/12. 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 8/36:01 am
CLE
- SXM
1 stop9h 43m
American Airlines
Thu 8/132:42 pm
SXM
- CLE
1 stop8h 56m
American Airlines
Deal found 6/12![American Airlines logo]()
$493
This Delta deal was found by Cheapflights users on 6/8. 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.
Thu 9/35:26 am
CLE
- SXM
1 stop8h 27m
Delta
Mon 9/73:18 pm
SXM
- CLE
1 stop9h 11m
Delta
Deal found 6/8![Delta logo]()
$493
This American Airlines deal was found by Cheapflights users on 6/9. 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 7/177:31 pm
CLE
- SXM
1 stop16h 02m
American Airlines
Fri 7/242:51 pm
SXM
- CLE
1 stop9h 38m
American Airlines
Deal found 6/9![American Airlines logo]()
$493
This Delta deal was found by Cheapflights users on 6/8. 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.
Wed 8/265:26 am
CLE
- SXM
1 stop8h 27m
Delta
Thu 9/33:18 pm
SXM
- CLE
1 stop9h 11m
Delta
Deal found 6/8![Delta logo]()
$493
This American Airlines deal was found by Cheapflights users on 6/7. 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.
Sun 8/96:15 am
CLE
- SXM
1 stop9h 24m
American Airlines
Sun 8/162:22 pm
SXM
- CLE
1 stop9h 28m
American Airlines
Deal found 6/7![American Airlines logo]()
$498
This American Airlines deal was found by Cheapflights users on 6/11. 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 7/46:11 pm
CLE
- SXM
2 stops19h 40m
American Airlines
Tue 7/72:19 pm
SXM
- CLE
2 stops18h 52m
American Airlines
Deal found 6/11![American Airlines logo]()
$498
This American Airlines deal was found by Cheapflights users on 6/12. 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 8/156:00 am
CLE
- SXM
1 stop6h 44m
American Airlines
Sat 8/224:39 pm
SXM
- CLE
2 stops19h 57m
American Airlines
Deal found 6/12![American Airlines logo]()
$498
Last-minute flights from Cleveland to Simpson BayDiscover last-minute flight deals from Cleveland to Simpson Bay. Data last updated June 12, 2026 and is based on user searches.
Discover last-minute flight deals from Cleveland to Simpson Bay. Data last updated June 12, 2026 and is based on user searches.
This Air Canada deal was found by Cheapflights users on 6/7. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/1310:10 am
CLE
- SXM
1 stop6h 50m
Air Canada
Sat 6/206:00 pm
SXM
- CLE
1 stop20h 05m
Air Canada
Deal found 6/7![Air Canada logo]()
$420
This Travelocity deal was found by Cheapflights users on 6/8. 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.
Sat 6/1310:10 am
CLE
- SXM
1 stop6h 50m
Multiple Airlines
Sat 6/2012:43 pm
SXM
- CLE
1 stop9h 52m
Multiple Airlines
Deal found 6/8![Multiple Airlines logo]()
$470
This American Airlines deal was found by Cheapflights users on 6/10. 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 6/275:45 am
CLE
- SXM
1 stop8h 05m
American Airlines
Thu 7/22:51 pm
SXM
- CLE
1 stop9h 38m
American Airlines
Deal found 6/10![American Airlines logo]()
$524
This American Airlines deal was found by Cheapflights users on 6/8. 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 6/296:01 am
CLE
- SXM
1 stop7h 21m
American Airlines
Mon 7/62:46 pm
SXM
- CLE
1 stop9h 04m
American Airlines
Deal found 6/8![American Airlines logo]()
$551
This American Airlines deal was found by Cheapflights users on 6/9. 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 7/46:11 pm
CLE
- SXM
2 stops19h 40m
American Airlines
Tue 7/72:19 pm
SXM
- CLE
2 stops18h 52m
American Airlines
Deal found 6/9![American Airlines logo]()
$498
This JetBlue deal was found by Cheapflights users on 6/7. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/116:25 am
CLE
- SXM
1 stop9h 57m
JetBlue
Wed 7/151:42 pm
SXM
- CLE
1 stop10h 13m
JetBlue
Deal found 6/7![JetBlue logo]()
$549
This United Airlines deal was found by Cheapflights users on 6/8. 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 7/186:00 am
CLE
- SXM
1 stop6h 33m
United Airlines
Sat 7/253:50 pm
SXM
- CLE
1 stop7h 54m
United Airlines
Deal found 6/8![United Airlines logo]()
$518
This Delta deal was found by Cheapflights users on 6/8. 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.
Tue 7/215:35 am
CLE
- SXM
1 stop8h 20m
Delta
Wed 7/293:20 pm
SXM
- CLE
1 stop17h 50m
Delta
Deal found 6/8![Delta logo]()
$493
This American Airlines deal was found by Cheapflights users on 6/11. 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 7/237:08 pm
CLE
- SXM
1 stop20h 36m
American Airlines
Mon 7/274:45 pm
SXM
- CLE
2 stops18h 27m
American Airlines
Deal found 6/11![American Airlines logo]()
$509
One-way flights from Cleveland to Simpson BaySearch for one-way flight options from Cleveland to Simpson Bay. Find affordable one-way fares based on user searches. Data last updated June 12, 2026.
Search for one-way flight options from Cleveland to Simpson Bay. Find affordable one-way fares based on user searches. Data last updated June 12, 2026.
This United Airlines deal was found by Cheapflights users on 6/9. 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 7/187:55 pm
CLE
- SXM
1 stop16h 38m
United Airlines
Deal found 6/9![United Airlines logo]()
$202
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 June 12, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $479 (Super.com) |
One-way from | $202 (United Airlines) |
Popular in | December |
Cheapest in | July |
Average price | $589 |
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 2,558,603 searches. Data last updated June 12, 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 - SXM
CLESXM
Cleveland Hopkins Intl
Mon 8/3
6:01 am-3:44 pm
1 stop9h 43m
Simpson Bay Princess Juliana
Thu 8/13
2:42 pm-11:38 pm
1 stop8h 56m
$493
Quickest round-trip
ClevelandSimpson Bay
CLE - SXM
CLESXM
Cleveland Hopkins Intl
Thu 9/3
5:26 am-1:53 pm
1 stop8h 27m
Simpson Bay Princess Juliana
Mon 9/7
3:18 pm-12:29 am
1 stop9h 11m
$493
ClevelandSimpson Bay
CLE - SXM
CLESXM
Cleveland Hopkins Intl
Fri 7/17
7:31 pm-11:33 am
1 stop16h 02m
Simpson Bay Princess Juliana
Fri 7/24
2:51 pm-12:29 am
1 stop9h 38m
$493
ClevelandSimpson Bay
CLE - SXM
CLESXM
Cleveland Hopkins Intl
Wed 8/26
5:26 am-1:53 pm
1 stop8h 27m
Simpson Bay Princess Juliana
Thu 9/3
3:18 pm-12:29 am
1 stop9h 11m
$493
ClevelandSimpson Bay
CLE - SXM
CLESXM
Cleveland Hopkins Intl
Sun 8/9
6:15 am-3:39 pm
1 stop9h 24m
Simpson Bay Princess Juliana
Sun 8/16
2:22 pm-11:50 pm
1 stop9h 28m
$498
ClevelandSimpson Bay
CLE - SXM
CLESXM
Cleveland Hopkins Intl
Sat 7/4
6:11 pm-1:51 pm
2 stops19h 40m
Simpson Bay Princess Juliana
Tue 7/7
2:19 pm-9:11 am
2 stops18h 52m
$498
ClevelandSimpson Bay
CLE - SXM
CLESXM
Cleveland Hopkins Intl
Sat 8/15
6:00 am-12:44 pm
1 stop6h 44m
Simpson Bay Princess Juliana
Sat 8/22
4:39 pm-12:36 pm
2 stops19h 57m
$498
Cheapest one-way
Quickest one-way
ClevelandSimpson Bay
CLE - SXM
CLESXM
Cleveland Hopkins Intl
Sat 7/18
7:55 pm-12:33 pm
1 stop16h 38m
$202
ClevelandSimpson Bay
CLE - SXM
CLESXM
Cleveland Hopkins Intl
Sat 7/18
7:34 pm-3:44 pm
2 stops20h 10m
$202
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 June.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | 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, July is the cheapest month in which you can book a flight from Cleveland to Simpson Bay (average of $498). Flying from Cleveland to Simpson Bay in December is currently the most expensive (average of $775). 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?
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 June 12, 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.
Overall
7.9
Food
7.2
Entertainment
7.8
Boarding
8.1
Comfort
7.8
Crew
8.5
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Overall
7.9
Food
7.2
Entertainment
7.8
Boarding
8.1
Comfort
7.8
Crew
8.5
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Overall
7.9
Food
7.2
Entertainment
7.8
Boarding
8.1
Comfort
7.8
Crew
8.5
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Overall
7.9
Food
7.2
Entertainment
7.8
Boarding
8.1
Comfort
7.8
Crew
8.5
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
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 June 12, 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 June 12, 2026.
Popular flight searches
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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 June 12, 2026.
Top 3 airlines flying from Cleveland to Simpson Bay
Discover the top 3 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 2,558,603 searches. Data last updated June 12, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$338 | Average$723 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$447 | Average$653 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$461 | Average$718 | FlexibilityNo cancel fee | On-time71% |