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Simpson Bay

$537+ 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 7/12. Fares are subject to change and may not be available on all flights or dates of travel.
CLE — SXM
Apr 22 — Apr 291
Tue 4/22
Tue 4/29
1 adult, Economy
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Cheap 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 April 17, 2025.

Most accurate provider

AranGrant
3 stars

Most trusted provider

AranGrant
3 stars

Round-trip from

$537
(American Airlines)

Popular in

January

Cheapest in

September

Average price

$663
Provider with most accurate pricing for Cleveland Hopkins Intl-Simpson Bay Princess Juliana flight deals.
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Provider most trusted by Cheapflights users for Cleveland Hopkins Intl-Simpson Bay Princess Juliana flights.
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From Cleveland Hopkins Intl to Simpson Bay Princess Juliana
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Highest demand for flights based on searches. 5% potential increase in price ($31 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($9 potential savings vs. average RT price).
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Average for round-trip flights in April 2025
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Find flight deals from Cleveland to Simpson Bay

Cheapest flights from Cleveland to Simpson Bay
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 April 17, 2025.

This American Airlines deal was found by Cheapflights users on 4/16. 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 7/127:42 pmCLE - SXM
1 stop17h 43mAmerican Airlines
Wed 7/164:05 pmSXM - CLE
1 stop7h 49mAmerican Airlines
Deal found 4/16$537
This Frontier deal was found by Cheapflights users on 4/17. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/189:56 pmCLE - SXM
1 stop13h 32mFrontier
Sat 7/266:26 pmSXM - CLE
2 stops15h 23mFrontier
Deal found 4/17$568
This Delta deal was found by Cheapflights users on 4/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/196:00 amCLE - SXM
1 stop7h 50mDelta
Sun 9/283:15 pmSXM - CLE
1 stop9h 21mDelta
Deal found 4/17$587
This Kiwi.com deal was found by Cheapflights users on 4/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/216:05 amCLE - SXM
1 stop7h 55mMultiple Airlines
Fri 4/256:26 pmSXM - CLE
1 stop10h 37mMultiple Airlines
Deal found 4/17$681
This United Airlines deal was found by Cheapflights users on 4/17. 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 4/196:00 amCLE - SXM
1 stop10h 49mUnited Airlines
Sat 4/261:25 pmSXM - CLE
1 stop20h 28mUnited Airlines
Deal found 4/17$1,144
This Air Canada deal was found by Cheapflights users on 4/17. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/1910:25 amCLE - SXM
2 stops28h 25mAir Canada
Fri 4/254:15 pmSXM - CLE
2 stops28h 39mAir Canada
Deal found 4/17$1,219

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 April 17, 2025.
Use the filters below to find and compare flights from Cleveland to Simpson Bay that are best for you.

Fly from

Cleveland

Fly to

Simpson Bay

Route

Depart

Return

Price

ClevelandSimpson Bay

CLE - SXM

CLESXM

Cleveland Hopkins Intl

Sat 7/12

7:42 pm-1:25 pm

1 stop17h 43m

Simpson Bay Princess Juliana

Wed 7/16

4:05 pm-11:54 pm

1 stop7h 49m

$537

ClevelandSimpson Bay

CLE - SXM

CLESXM

Cleveland Hopkins Intl

Fri 7/18

9:56 pm-11:28 am

1 stop13h 32m

Simpson Bay Princess Juliana

Sat 7/26

6:26 pm-9:49 am

2 stops15h 23m

$568

ClevelandSimpson Bay

CLE - SXM

CLESXM

Cleveland Hopkins Intl

Fri 9/19

6:00 am-1:50 pm

1 stop7h 50m

Simpson Bay Princess Juliana

Sun 9/28

3:15 pm-12:36 am

1 stop9h 21m

$587

ClevelandSimpson Bay

CLE - SXM

CLESXM

Cleveland Hopkins Intl

Wed 5/21

2:49 pm-1:15 pm

2 stops22h 26m

Simpson Bay Princess Juliana

Mon 5/26

6:15 pm-12:51 pm

1 stop18h 36m

$772

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/16

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 April.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*2 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy3 starsTrust Score*3 stars
CheapflightsfaresPrice Accuracy3 starsTrust Score*2 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Cleveland-Simpson Bay flights, users find the pricing of AranGrant to be most consistent on Cheapflights vs. AranGrant Users can find the same prices on Cleveland-Simpson Bay flight deals on Cheapflights vs. AranGrant >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 AranGrant the most. AranGrant 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.
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?

Use this chart to determine the optimal time to book a round-trip flight from Cleveland to Simpson Bay. Price data was last updated on April 11, 2025.

The best time to book flights from Cleveland to Simpson Bay is 25 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, September is the cheapest month in which you can book a flight from Cleveland to Simpson Bay (average of $459). Flying from Cleveland to Simpson Bay in July is currently the most expensive (average of $675). 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.

What is the cheapest time of day to fly from CLE to SXM?

Find hourly flight availability from Cleveland to Simpson Bay. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated April 17, 2025.

A simple way to save on the total cost of your ticket is to fly from Cleveland to Simpson Bay at noon. If you’re flexible enough to do this you can expect to save up to 21% on your trip compared to booking a flight in the morning.

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 April 17, 2025.
Delta
8.0
Very good
7,917 reviews

Boarding

8.2

Overall

8.0

Food

7.3

Crew

8.5

Comfort

7.9

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Delta
8.0
Very good
7,917 reviews
Delta
8.0
Very good
7,917 reviews

Boarding

8.2

Overall

8.0

Food

7.3

Crew

8.5

Comfort

7.9

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,917 reviews

Boarding

8.2

Overall

8.0

Food

7.3

Crew

8.5

Comfort

7.9

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Frontier
6.0
Okay
3,281 reviews
Delta
8.0
Very good
7,917 reviews

Boarding

8.2

Overall

8.0

Food

7.3

Crew

8.5

Comfort

7.9

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

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.

  • What are the cheapest airlines flying from Cleveland to Simpson Bay round-trip?

    According to our current data, American Airlines ($537), Frontier ($650), and Delta ($800) offers the cheapest pricing from Cleveland to Simpson Bay. American Airlines is priced at 11% lower than the current average price of a flight leaving 3 months from now.

  • Can I find deals for flights from Cleveland to Simpson Bay that include hotel bookings?

    Yes. In addition to deals on Cleveland to Simpson Bay flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Cleveland to Simpson Bay?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Cleveland to Simpson Bay.

  • Can I find deals for business class flights from Cleveland to Simpson Bay?

    Yes. Cheapflights offers flight deals from Cleveland to Simpson Bay by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Cleveland to Simpson Bay?

    Currently, September is the cheapest month in which you can book a flight from Cleveland to Simpson Bay (average of $459). Flying from Cleveland to Simpson Bay in July is currently the most expensive (average of $675). 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.

See more FAQs

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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 2,558,603 searches. Data last updated April 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$269Average$410FlexibilityNo cancel feeOn-time65%
DeltaCheapest$333Average$588FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$455Average$645FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$458Average$651FlexibilityNo cancel feeOn-time71%

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