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Simpson Bay

$197+ 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 8/27. Fares are subject to change and may not be available on all flights or dates of travel.
CLE — SXM
Aug 26 — Sep 21
Wed 8/26
Wed 9/2
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 July 27, 2026.

This Delta deal was found by Cheapflights users on 7/22. 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 10/197:05 am
CLE
-
SXM
1 stop6h 44m
Delta
Wed 10/283:14 pm
SXM
-
CLE
1 stop9h 34m
Delta
Deal found 7/22$367
This Delta deal was found by Cheapflights users on 7/27. 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 9/216:00 am
CLE
-
SXM
1 stop7h 53m
Delta
Fri 9/253:18 pm
SXM
-
CLE
1 stop9h 21m
Delta
Deal found 7/27$377
This Cheapflightsfares deal was found by Cheapflights users on 7/25. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/187:00 am
CLE
-
SXM
1 stop7h 00m
JetBlue
Fri 9/253:05 pm
SXM
-
CLE
1 stop8h 27m
JetBlue
Deal found 7/25$424
This JetBlue deal was found by Cheapflights users on 7/27. 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 9/197:00 am
CLE
-
SXM
1 stop7h 00m
JetBlue
Fri 9/253:05 pm
SXM
-
CLE
1 stop8h 27m
JetBlue
Deal found 7/27$427
This Air Canada deal was found by Cheapflights users on 7/24. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/162:45 pm
CLE
-
SXM
2 stops26h 15m
Air Canada
Sun 10/253:45 pm
SXM
-
CLE
1 stop26h 32m
Air Canada
Deal found 7/24$428
This American Airlines deal was found by Cheapflights users on 7/22. 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 9/194:32 pm
CLE
-
SXM
2 stops20h 51m
American Airlines
Wed 9/232:23 pm
SXM
-
CLE
1 stop9h 23m
American Airlines
Deal found 7/22$430
This United Airlines deal was found by Cheapflights users on 7/26. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/77:12 pm
CLE
-
SXM
1 stop17h 38m
United Airlines
Tue 12/152:52 pm
SXM
-
CLE
1 stop22h 06m
United Airlines
Deal found 7/26$436
This Travelocity deal was found by Cheapflights users on 7/22. 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.
Wed 10/217:00 pm
CLE
-
SXM
1 stop22h 00m
Multiple Airlines
Wed 10/281:35 pm
SXM
-
CLE
1 stop10h 24m
Multiple Airlines
Deal found 7/22$438
This American Airlines deal was found by Cheapflights users on 7/26. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/76:01 am
CLE
-
SXM
2 stops9h 24m
American Airlines
Tue 12/155:25 pm
SXM
-
CLE
2 stops20h 26m
American Airlines
Deal found 7/26$440
This Justfly.com deal was found by Cheapflights users on 7/22. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2210:00 am
CLE
-
SXM
1 stop7h 00m
Multiple Airlines
Tue 10/271:35 pm
SXM
-
CLE
1 stop10h 24m
Multiple Airlines
Deal found 7/22$443

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 July 27, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$367
(Delta)

One-way from

$197
(Southwest)

Popular in

November

Cheapest in

April

Average price

$513
Provider with most accurate pricing for Cleveland Hopkins Intl-Simpson Bay Princess Juliana flight deals.
Search Deals
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. 11% potential increase in price ($82 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($12 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 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 July 27, 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

Price

Cheapest round-trip

ClevelandSimpson Bay

CLE - SXM

CLESXM

Cleveland Hopkins Intl

Mon 1/4

6:00 pm-12:15 pm

1 stop17h 15m

Simpson Bay Princess Juliana

Wed 1/13

1:40 pm-12:35 am

1 stop11h 55m

$384

ClevelandSimpson Bay

CLE - SXM

CLESXM

Cleveland Hopkins Intl

Mon 1/4

6:00 pm-12:15 pm

1 stop17h 15m

Simpson Bay Princess Juliana

Sat 1/16

5:25 pm-12:35 am

1 stop8h 10m

$409

ClevelandSimpson Bay

CLE - SXM

CLESXM

Cleveland Hopkins Intl

Fri 10/16

7:00 pm-5:00 pm

1 stop22h 00m

Simpson Bay Princess Juliana

Sun 10/25

3:45 pm-6:17 pm

1 stop26h 32m

$424

ClevelandSimpson Bay

CLE - SXM

CLESXM

Cleveland Hopkins Intl

Mon 12/7

7:12 pm-1:50 pm

1 stop17h 38m

Simpson Bay Princess Juliana

Tue 12/15

2:52 pm-11:58 am

1 stop22h 06m

$436

ClevelandSimpson Bay

CLE - SXM

CLESXM

Cleveland Hopkins Intl

Tue 10/20

6:00 am-1:25 pm

1 stop7h 25m

Simpson Bay Princess Juliana

Mon 10/26

1:35 pm-11:59 pm

1 stop10h 24m

$459

ClevelandSimpson Bay

CLE - SXM

CLESXM

Cleveland Hopkins Intl

Sun 8/30

6:25 am-1:54 pm

1 stop7h 29m

Simpson Bay Princess Juliana

Thu 9/3

1:42 pm-11:54 pm

1 stop10h 12m

$459

ClevelandSimpson Bay

CLE - SXM

CLESXM

Cleveland Hopkins Intl

Mon 10/19

6:00 am-1:25 pm

1 stop7h 25m

Simpson Bay Princess Juliana

Tue 10/27

1:35 pm-11:59 pm

1 stop10h 24m

$459
Quickest round-trip

ClevelandSimpson Bay

CLE - SXM

CLESXM

Cleveland Hopkins Intl

Thu 10/22

6:00 am-1:49 pm

1 stop7h 49m

Simpson Bay Princess Juliana

Thu 10/29

3:14 pm-12:48 am

1 stop9h 34m

$495

ClevelandSimpson Bay

CLE - SXM

CLESXM

Cleveland Hopkins Intl

Tue 11/24

6:00 am-2:45 pm

1 stop7h 45m

Simpson Bay Princess Juliana

Thu 12/3

4:10 pm-9:13 am

1 stop18h 03m

$495
Cheapest one-way

ClevelandSimpson Bay

CLE - SXM

CLESXM

Cleveland Hopkins Intl

Thu 8/27

4:15 pm-2:05 pm

2 stops21h 50m

$197

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/23

Showing 1-10 of 11 resultsSorted by cheapest first
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 July.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy3 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 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?

The best time to book flights from Cleveland to Simpson Bay is 82 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 $751). 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?

Airfare is below average for this route at the moment.

Cleveland to Simpson Bay flights typically cost between $483 and $781 in October.
The cheapest round-trip price found within the last 5 days was $367 on Delta (Oct 19-Oct 28).

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 July 27, 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.
Delta
7.8
Good
8,482 reviews

Overall

7.8

Comfort

7.8

Crew

8.5

Food

7.2

Boarding

8.1

Entertainment

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,May 2026

SEA - KOA

The snacks were not very good, not everyone was very friendly and professional
Delta
7.8
Good
8,482 reviews
Delta
7.8
Good
8,482 reviews

Overall

7.8

Comfort

7.8

Crew

8.5

Food

7.2

Boarding

8.1

Entertainment

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,May 2026

SEA - KOA

The snacks were not very good, not everyone was very friendly and professional
United Airlines
7.4
Good
10,041 reviews
Delta
7.8
Good
8,482 reviews

Overall

7.8

Comfort

7.8

Crew

8.5

Food

7.2

Boarding

8.1

Entertainment

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,May 2026

SEA - KOA

The snacks were not very good, not everyone was very friendly and professional
American Airlines
7.1
Good
11,836 reviews
Delta
7.8
Good
8,482 reviews

Overall

7.8

Comfort

7.8

Crew

8.5

Food

7.2

Boarding

8.1

Entertainment

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,May 2026

SEA - KOA

The snacks were not very good, not everyone was very friendly and professional

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 $384, Delta can have you in Simpson Bay from Cleveland in 17h 15m. 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, Delta ($285), United Airlines ($447), and American Airlines ($461) offers the cheapest pricing from Cleveland to Simpson Bay. Delta is priced at 54% 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, 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 $751). 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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Complete your trip

Complete your trip to Simpson Bay by adding a car rental and/or hotel reservation to your travel itinerary.
Simpson Bay Princess Juliana Airport car rentals

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 July 27, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$225Average$665FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$447Average$653FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$461Average$716FlexibilityNo cancel feeOn-time71%

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