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Simpson Bay

$291+ 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 11/10. Fares are subject to change and may not be available on all flights or dates of travel.
CLE — SXM
Nov 27 — Dec 41
Thu 11/27
Thu 12/4
1 adult, Economy
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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 October 28, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/26. 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 11/105:45 amCLE - SXM
1 stop7h 30mMultiple Airlines
Fri 11/143:20 pmSXM - CLE
1 stop8h 51mMultiple Airlines
Deal found 10/26$291
This Kiwi.com deal was found by Cheapflights users on 10/26. 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 11/105:45 amCLE - SXM
1 stop7h 30mMultiple Airlines
Thu 11/2011:30 amSXM - CLE
2 stops12h 00mMultiple Airlines
Deal found 10/26$341
This Kiwi.com deal was found by Cheapflights users on 10/26. 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.
Sun 11/97:51 pmCLE - SXM
2 stops17h 24mMultiple Airlines
Fri 11/143:20 pmSXM - CLE
1 stop8h 51mMultiple Airlines
Deal found 10/26$344
This Kiwi.com deal was found by Cheapflights users on 10/26. 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 11/105:45 amCLE - SXM
1 stop7h 30mMultiple Airlines
Mon 11/173:20 pmSXM - CLE
2 stops32h 07mMultiple Airlines
Deal found 10/26$353
This Cheapflightsfares deal was found by Cheapflights users on 10/26. 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.
Mon 11/105:45 amCLE - SXM
1 stop7h 30mSpirit Airlines
Mon 11/173:20 pmSXM - CLE
1 stop9h 39mSpirit Airlines
Deal found 10/26$360
This Kiwi.com deal was found by Cheapflights users on 10/26. 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.
Tue 11/111:56 pmCLE - SXM
2 stops28h 56mMultiple Airlines
Fri 11/143:20 pmSXM - CLE
1 stop8h 51mMultiple Airlines
Deal found 10/26$372
This Kiwi.com deal was found by Cheapflights users on 10/26. 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 11/105:45 amCLE - SXM
1 stop7h 30mMultiple Airlines
Sat 11/153:20 pmSXM - CLE
2 stops32h 07mMultiple Airlines
Deal found 10/26$400
This Kiwi.com deal was found by Cheapflights users on 10/26. 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.
Fri 11/147:51 pmCLE - SXM
2 stops17h 24mMultiple Airlines
Fri 11/213:20 pmSXM - CLE
1 stop21h 10mMultiple Airlines
Deal found 10/26$418
This Kiwi.com deal was found by Cheapflights users on 10/26. 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.
Thu 11/137:20 amCLE - SXM
2 stops29h 55mMultiple Airlines
Mon 11/173:20 pmSXM - CLE
1 stop8h 51mMultiple Airlines
Deal found 10/26$426

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 October 28, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$291
(Kiwi.com)

Popular in

December

Cheapest in

May

Average price

$716
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
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($58 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
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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 October 28, 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

Fri 11/7

9:00 pm-2:15 pm

2 stops16h 15m

Simpson Bay Princess Juliana

Fri 11/14

3:20 pm-11:11 pm

1 stop8h 51m

$458

ClevelandSimpson Bay

CLE - SXM

CLESXM

Cleveland Hopkins Intl

Sun 2/1

1:16 pm-3:10 pm

3 stops24h 54m

Simpson Bay Princess Juliana

Sat 2/7

4:28 pm-12:21 pm

2 stops20h 53m

$463

ClevelandSimpson Bay

CLE - SXM

CLESXM

Cleveland Hopkins Intl

Fri 11/14

4:45 pm-2:15 pm

1 stop20h 30m

Simpson Bay Princess Juliana

Fri 11/21

3:20 pm-1:11 pm

1 stop22h 51m

$473

ClevelandSimpson Bay

CLE - SXM

CLESXM

Cleveland Hopkins Intl

Thu 12/11

6:10 pm-4:00 pm

1 stop20h 50m

Simpson Bay Princess Juliana

Thu 12/18

3:40 pm-5:30 pm

2 stops26h 50m

$488

ClevelandSimpson Bay

CLE - SXM

CLESXM

Cleveland Hopkins Intl

Mon 3/30

6:15 pm-1:35 pm

2 stops19h 20m

Simpson Bay Princess Juliana

Fri 4/3

4:00 pm-5:30 pm

1 stop25h 30m

$496

ClevelandSimpson Bay

CLE - SXM

CLESXM

Cleveland Hopkins Intl

Sun 12/21

1:50 pm-2:15 pm

1 stop23h 25m

Simpson Bay Princess Juliana

Wed 12/31

3:20 pm-10:29 am

1 stop20h 09m

$520

ClevelandSimpson Bay

CLE - SXM

CLESXM

Cleveland Hopkins Intl

Sat 2/14

6:10 pm-2:40 pm

2 stops19h 30m

Simpson Bay Princess Juliana

Sat 2/21

4:28 pm-11:20 am

1 stop19h 52m

$525

ClevelandSimpson Bay

CLE - SXM

CLESXM

Cleveland Hopkins Intl

Sat 2/7

6:26 pm-12:58 pm

1 stop17h 32m

Simpson Bay Princess Juliana

Fri 2/13

3:20 pm-12:30 am

1 stop10h 10m

$537

ClevelandSimpson Bay

CLE - SXM

CLESXM

Cleveland Hopkins Intl

Sat 3/7

6:57 pm-12:50 pm

1 stop16h 53m

Simpson Bay Princess Juliana

Wed 3/11

2:15 pm-10:35 pm

1 stop8h 20m

$537

ClevelandSimpson Bay

CLE - SXM

CLESXM

Cleveland Hopkins Intl

Sat 11/1

7:25 am-10:50 am

3 stops51h 25m

$368

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/28

Showing 1-10 of 11 results
1
2

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.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy2 starsTrust Score*3 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 eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Cleveland-Simpson Bay flight deals on Cheapflights vs. eDreams >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 eDreams the most. eDreams 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 October 24, 2025.

The best time to book flights from Cleveland to Simpson Bay is 72 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, March is the cheapest month in which you can book a flight from Cleveland to Simpson Bay (average of $188). Flying from Cleveland to Simpson Bay in December is currently the most expensive (average of $537). 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 28, 2025.
Peruse reviews from past customers who have flown with Delta, United Airlines, and American 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.
Delta
7.9
Good
7,994 reviews

Boarding

8.2

Crew

8.5

Overall

7.9

Comfort

7.9

Food

7.3

Entertainment

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
Delta
7.9
Good
7,994 reviews
Delta
7.9
Good
7,994 reviews

Boarding

8.2

Crew

8.5

Overall

7.9

Comfort

7.9

Food

7.3

Entertainment

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
United Airlines
7.4
Good
9,001 reviews
Delta
7.9
Good
7,994 reviews

Boarding

8.2

Crew

8.5

Overall

7.9

Comfort

7.9

Food

7.3

Entertainment

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
American Airlines
7.2
Good
11,032 reviews
Delta
7.9
Good
7,994 reviews

Boarding

8.2

Crew

8.5

Overall

7.9

Comfort

7.9

Food

7.3

Entertainment

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.

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.

  • How long is the flight from Cleveland to Simpson Bay?

    For as low as $488, Spirit Airlines can have you in Simpson Bay from Cleveland in 20h 50m. Airlines will cover a distance of 1957 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

    According to our current data, United Airlines ($455), Delta ($460), and American Airlines ($537) offers the cheapest pricing from Cleveland to Simpson Bay. United Airlines is priced at 31% 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, March is the cheapest month in which you can book a flight from Cleveland to Simpson Bay (average of $188). Flying from Cleveland to Simpson Bay in December is currently the most expensive (average of $537). 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

Traveling to a place near Simpson Bay?

Book flights to Simpson Bay if you plan to visit one of these locations
Philipsburg

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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 October 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$455Average$677FlexibilityNo cancel feeOn-time69%
DeltaCheapest$460Average$624FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$537Average$691FlexibilityNo cancel feeOn-time71%

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