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Simpson Bay

$391+ 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 7/31. Fares are subject to change and may not be available on all flights or dates of travel.
CLE — SXM
août 3 — août 101
dim. 8/3
dim. 8/10
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 juillet 29, 2025.

Round-trip from

$481
(Justfly.com)

Popular in

December

Cheapest in

November

Average price

$624
From Cleveland Hopkins Intl to Simpson Bay Princess Juliana
Search Deals
Highest demand for flights based on searches. 3% potential increase in price ($25 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($13 potential savings vs. average RT price).
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Average for round-trip flights in July 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 juillet 29, 2025.

This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 7/317:26 pmCLE - SXM
2 stops40h 02mFrontier
sam. 8/26:26 pmSXM - CLE
1 stop16h 11mFrontier
Deal found 7/27$391
This Justfly.com deal was found by Cheapflights users on 7/28. 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.
mar. 11/184:52 pmCLE - SXM
1 stop21h 18mMultiple Airlines
sam. 11/223:40 pmSXM - CLE
2 stops26h 56mMultiple Airlines
Deal found 7/28$481
This American Airlines deal was found by Cheapflights users on 7/29. 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.
lun. 12/296:11 amCLE - SXM
1 stop6h 14mAmerican Airlines
mer. 1/73:25 pmSXM - CLE
1 stop7h 30mAmerican Airlines
Deal found 7/29$537
This Air Canada deal was found by Cheapflights users on 7/28. 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.
mer. 11/196:15 pmCLE - SXM
2 stops19h 25mAir Canada
sam. 11/223:40 pmSXM - CLE
2 stops26h 56mAir Canada
Deal found 7/28$553
This JetBlue deal was found by Cheapflights users on 7/29. 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.
dim. 12/2810:15 pmCLE - SXM
1 stop11h 59mJetBlue
dim. 1/412:30 pmSXM - CLE
1 stop9h 50mJetBlue
Deal found 7/29$559
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.
mer. 9/36:00 amCLE - SXM
1 stop7h 45mDelta
dim. 9/73:21 pmSXM - CLE
1 stop9h 19mDelta
Deal found 7/27$562
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 7/317:47 pmCLE - SXM
3 stops18h 13mSpirit Airlines
sam. 8/23:05 pmSXM - CLE
3 stops24h 03mSpirit Airlines
Deal found 7/27$1,032

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 juillet 29, 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

mar. 11/18

4:52 pm-3:10 pm

1 stop21h 18m

Simpson Bay Princess Juliana

sam. 11/22

3:40 pm-5:36 pm

2 stops26h 56m

$481

ClevelandSimpson Bay

CLE - SXM

CLESXM

Cleveland Hopkins Intl

dim. 1/18

12:15 pm-3:10 pm

1 stop25h 55m

Simpson Bay Princess Juliana

mer. 1/21

4:28 pm-11:20 am

1 stop19h 52m

$482

ClevelandSimpson Bay

CLE - SXM

CLESXM

Cleveland Hopkins Intl

lun. 12/29

6:11 am-1:25 pm

1 stop6h 14m

Simpson Bay Princess Juliana

mer. 1/7

3:25 pm-9:55 pm

1 stop7h 30m

$537

ClevelandSimpson Bay

CLE - SXM

CLESXM

Cleveland Hopkins Intl

mer. 11/19

6:15 pm-2:40 pm

2 stops19h 25m

Simpson Bay Princess Juliana

sam. 11/22

3:40 pm-5:36 pm

2 stops26h 56m

$553

ClevelandSimpson Bay

CLE - SXM

CLESXM

Cleveland Hopkins Intl

dim. 12/28

10:15 pm-11:14 am

1 stop11h 59m

Simpson Bay Princess Juliana

dim. 1/4

12:30 pm-9:20 pm

1 stop9h 50m

$559

ClevelandSimpson Bay

CLE - SXM

CLESXM

Cleveland Hopkins Intl

mer. 9/3

6:00 am-1:45 pm

1 stop7h 45m

Simpson Bay Princess Juliana

dim. 9/7

3:21 pm-12:40 am

1 stop9h 19m

$562

ClevelandSimpson Bay

CLE - SXM

CLESXM

Cleveland Hopkins Intl

sam. 11/1

6:05 pm-3:57 pm

1 stop21h 52m

$616

ClevelandSimpson Bay

CLE - SXM

CLESXM

Cleveland Hopkins Intl

sam. 11/1

3:36 pm-2:17 pm

2 stops22h 41m

$776

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/27

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 July 25, 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 March is currently the most expensive (average of $655). 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 juillet 29, 2025.
Peruse reviews from past customers who have flown with Delta, United Airlines, and JetBlue 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
8.0
Very good
7,977 reviews

Crew

8.5

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Food

7.3

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,977 reviews
Delta
8.0
Very good
7,977 reviews

Crew

8.5

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Food

7.3

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
United Airlines
7.4
Good
8,899 reviews
Delta
8.0
Very good
7,977 reviews

Crew

8.5

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Food

7.3

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
JetBlue
7.3
Good
2,913 reviews
Delta
8.0
Very good
7,977 reviews

Crew

8.5

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Food

7.3

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,977 reviews

Crew

8.5

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Food

7.3

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Air Canada
7.1
Good
9,822 reviews
Delta
8.0
Very good
7,977 reviews

Crew

8.5

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Food

7.3

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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, Spirit Airlines ($482), American Airlines ($537), and Air Canada ($553) offers the cheapest pricing from Cleveland to Simpson Bay. Spirit Airlines is priced at 24% 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 March is currently the most expensive (average of $655). 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 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 juillet 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$333Average$594FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$455Average$644FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$456Average$683FlexibilityNo cancel feeOn-time71%

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