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Simpson Bay

$97+ 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 2/23. Fares are subject to change and may not be available on all flights or dates of travel.
CLE — SXM
Feb 25 — Mar 41
Wed 2/25
Wed 3/4
1 adult, Economy
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Cheap 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 January 26, 2026.

This Priceline deal was found by Cheapflights users on 1/24. 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.
Sun 2/17:21 pm
CLE
-
SXM
1 stop17h 54m
Multiple Airlines
Sat 2/73:10 pm
SXM
-
CLE
1 stop9h 01m
Multiple Airlines
Deal found 1/24$266
This Kiwi.com deal was found by Cheapflights users on 1/26. 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.
Sat 4/185:35 pm
CLE
-
SXM
1 stop19h 41m
Multiple Airlines
Wed 4/222:11 pm
SXM
-
CLE
1 stop23h 03m
Multiple Airlines
Deal found 1/26$354
This Kiwi.com deal was found by Cheapflights users on 1/25. 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.
Sat 4/185:35 pm
CLE
-
SXM
1 stop19h 41m
Spirit Airlines
Tue 4/212:11 pm
SXM
-
CLE
1 stop26h 29m
Spirit Airlines
Deal found 1/25$365
This Kiwi.com deal was found by Cheapflights users on 1/24. 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 5/115:35 pm
CLE
-
SXM
1 stop19h 41m
Spirit Airlines
Fri 5/152:11 pm
SXM
-
CLE
1 stop26h 29m
Spirit Airlines
Deal found 1/24$371
This Kiwi.com deal was found by Cheapflights users on 1/25. 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.
Wed 3/117:30 am
CLE
-
SXM
1 stop29h 38m
Multiple Airlines
Wed 3/182:14 pm
SXM
-
CLE
1 stop24h 13m
Multiple Airlines
Deal found 1/25$386
This Kiwi.com deal was found by Cheapflights users on 1/25. 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.
Wed 4/158:15 am
CLE
-
SXM
1 stop29h 01m
Multiple Airlines
Sun 4/192:11 pm
SXM
-
CLE
1 stop26h 29m
Multiple Airlines
Deal found 1/25$387
This JetBlue deal was found by Cheapflights users on 1/24. 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 5/96:00 am
CLE
-
SXM
1 stop9h 20m
JetBlue
Sat 5/1612:30 pm
SXM
-
CLE
1 stop11h 25m
JetBlue
Deal found 1/24$393
This Trip.com deal was found by Cheapflights users on 1/24. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/25:44 pm
CLE
-
SXM
1 stop19h 31m
Multiple Airlines
Sun 3/82:20 pm
SXM
-
CLE
1 stop11h 05m
Multiple Airlines
Deal found 1/24$398
This American Airlines deal was found by Cheapflights users on 1/24. 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 3/76:22 pm
CLE
-
SXM
1 stop16h 07m
American Airlines
Wed 3/1112:29 pm
SXM
-
CLE
1 stop11h 29m
American Airlines
Deal found 1/24$417

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 January 26, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$354
(Kiwi.com)

One-way from

$97
(Kiwi.com)

Popular in

December

Cheapest in

May

Average price

$622
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
One-way flight from Cleveland Hopkins Intl to Simpson Bay Princess Juliana
Search Deals
Highest demand for flights based on searches. 5% potential increase in price ($38 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($9 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

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 January 26, 2026.
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

Sun 2/1

7:21 pm-2:15 pm

1 stop17h 54m

Simpson Bay Princess Juliana

Sat 2/7

3:10 pm-11:11 pm

1 stop9h 01m

$266

ClevelandSimpson Bay

CLE - SXM

CLESXM

Cleveland Hopkins Intl

Sat 4/18

5:35 pm-1:16 pm

1 stop19h 41m

Simpson Bay Princess Juliana

Wed 4/22

2:11 pm-1:14 pm

1 stop23h 03m

$354

ClevelandSimpson Bay

CLE - SXM

CLESXM

Cleveland Hopkins Intl

Sat 4/18

5:35 pm-1:16 pm

1 stop19h 41m

Simpson Bay Princess Juliana

Tue 4/21

2:11 pm-4:40 pm

1 stop26h 29m

$365

ClevelandSimpson Bay

CLE - SXM

CLESXM

Cleveland Hopkins Intl

Wed 4/15

8:15 am-1:16 pm

1 stop29h 01m

Simpson Bay Princess Juliana

Sun 4/19

2:11 pm-4:40 pm

1 stop26h 29m

$387

ClevelandSimpson Bay

CLE - SXM

CLESXM

Cleveland Hopkins Intl

Mon 3/2

5:44 pm-2:15 pm

1 stop19h 31m

Simpson Bay Princess Juliana

Sun 3/8

2:20 pm-1:25 am

1 stop11h 05m

$398

ClevelandSimpson Bay

CLE - SXM

CLESXM

Cleveland Hopkins Intl

Sat 3/7

6:22 pm-11:29 am

1 stop16h 07m

Simpson Bay Princess Juliana

Wed 3/11

12:29 pm-11:58 pm

1 stop11h 29m

$417

ClevelandSimpson Bay

CLE - SXM

CLESXM

Cleveland Hopkins Intl

Wed 3/11

10:00 pm-1:08 pm

2 stops15h 08m

Simpson Bay Princess Juliana

Wed 3/18

2:14 pm-2:27 pm

1 stop24h 13m

$417

ClevelandSimpson Bay

CLE - SXM

CLESXM

Cleveland Hopkins Intl

Sat 4/18

6:49 pm-1:16 pm

2 stops18h 27m

Simpson Bay Princess Juliana

Tue 4/21

4:35 pm-12:19 pm

2 stops19h 44m

$422

ClevelandSimpson Bay

CLE - SXM

CLESXM

Cleveland Hopkins Intl

Mon 2/23

6:55 am-2:15 pm

1 stop30h 20m

$97

ClevelandSimpson Bay

CLE - SXM

CLESXM

Cleveland Hopkins Intl

Sun 2/22

8:48 pm-2:15 pm

2 stops16h 27m

$100

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/24

Showing 1-10 of 14 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 January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy2 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 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.
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 January 23, 2026.

The best time to book flights from Cleveland to Simpson Bay is 47 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 $194). 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 January 26, 2026.
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
8,113 reviews

Boarding

8.1

Food

7.2

Entertainment

7.8

Comfort

7.9

Overall

7.9

Crew

8.5

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Delta
7.9
Good
8,113 reviews
Delta
7.9
Good
8,113 reviews

Boarding

8.1

Food

7.2

Entertainment

7.8

Comfort

7.9

Overall

7.9

Crew

8.5

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
United Airlines
7.4
Good
9,200 reviews
Delta
7.9
Good
8,113 reviews

Boarding

8.1

Food

7.2

Entertainment

7.8

Comfort

7.9

Overall

7.9

Crew

8.5

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
American Airlines
7.2
Good
11,189 reviews
Delta
7.9
Good
8,113 reviews

Boarding

8.1

Food

7.2

Entertainment

7.8

Comfort

7.9

Overall

7.9

Crew

8.5

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Frontier
5.7
Fair
3,058 reviews
Delta
7.9
Good
8,113 reviews

Boarding

8.1

Food

7.2

Entertainment

7.8

Comfort

7.9

Overall

7.9

Crew

8.5

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

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 $365, Spirit Airlines can have you in Simpson Bay from Cleveland in 19h 41m. Airlines will cover a distance of 1957 mi.

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

    According to our current data, Frontier ($185), Delta ($486), and United Airlines ($488) offers the cheapest pricing from Cleveland to Simpson Bay. Frontier is priced at 72% 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 $194). 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 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 January 26, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$185Average$313FlexibilityNo cancel feeOn-time62%
DeltaCheapest$486Average$665FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$488Average$706FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$499Average$712FlexibilityNo cancel feeOn-time71%

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