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Simpson Bay

$263+ 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 6/26. Fares are subject to change and may not be available on all flights or dates of travel.
CLE — SXM
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
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 June 12, 2025.

Round-trip from

$263
(Priceline)

Popular in

June

Cheapest in

September

Average price

$755
From Cleveland Hopkins Intl to Simpson Bay Princess Juliana
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($45 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($14 potential savings vs. average RT price).
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Average for round-trip flights in June 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 June 12, 2025.

This Priceline deal was found by Cheapflights users on 6/12. 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.
Thu 6/268:25 pmCLE - SXM
1 stop20h 51mFrontier
Sat 7/126:26 pmSXM - CLE
1 stop16h 11mFrontier
Deal found 6/12$263
This FlightHub deal was found by Cheapflights users on 6/11. 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.
Sat 8/168:00 amCLE - SXM
1 stop9h 21mMultiple Airlines
Sat 8/233:27 pmSXM - CLE
1 stop8h 52mMultiple Airlines
Deal found 6/11$345
This Delta deal was found by Cheapflights users on 6/10. 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 stop7h 51mDelta
Deal found 6/10$477
This American Airlines deal was found by Cheapflights users on 6/11. 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.
Thu 9/48:03 pmCLE - SXM
2 stops17h 16mAmerican Airlines
Thu 9/112:45 pmSXM - CLE
1 stop8h 05mAmerican Airlines
Deal found 6/11$482
This Mytrip deal was found by Cheapflights users on 6/12. 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.
Thu 6/268:13 pmCLE - SXM
2 stops17h 47mSpirit Airlines
Sat 7/123:05 pmSXM - CLE
2 stops27h 47mSpirit Airlines
Deal found 6/12$498
This Gotogate deal was found by Cheapflights users on 6/12. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/276:15 pmCLE - SXM
2 stops18h 40mAir Canada
Sat 1/33:05 pmSXM - CLE
2 stops51h 31mAir Canada
Deal found 6/12$1,784

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 June 12, 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

Thu 6/26

8:25 pm-5:16 pm

1 stop20h 51m

Simpson Bay Princess Juliana

Sat 7/12

6:26 pm-10:37 am

1 stop16h 11m

$263

ClevelandSimpson Bay

CLE - SXM

CLESXM

Cleveland Hopkins Intl

Sat 8/16

8:00 am-5:21 pm

1 stop9h 21m

Simpson Bay Princess Juliana

Sat 8/23

3:27 pm-12:19 am

1 stop8h 52m

$345

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-11:06 pm

1 stop7h 51m

$477

ClevelandSimpson Bay

CLE - SXM

CLESXM

Cleveland Hopkins Intl

Thu 9/4

8:03 pm-1:19 pm

2 stops17h 16m

Simpson Bay Princess Juliana

Thu 9/11

2:45 pm-10:50 pm

1 stop8h 05m

$482

ClevelandSimpson Bay

CLE - SXM

CLESXM

Cleveland Hopkins Intl

Thu 6/26

8:13 pm-2:00 pm

2 stops17h 47m

Simpson Bay Princess Juliana

Sat 7/12

3:05 pm-6:52 pm

2 stops27h 47m

$498

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/12

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 June 9, 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 $657). 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 June 12, 2025.
Delta
8.0
Very good
7,946 reviews

Overall

8.0

Food

7.3

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Crew

8.5

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
7,946 reviews
Delta
8.0
Very good
7,946 reviews

Overall

8.0

Food

7.3

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Crew

8.5

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
7,946 reviews

Overall

8.0

Food

7.3

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Crew

8.5

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!
Spirit Airlines
6.3
Okay
8,052 reviews
Delta
8.0
Very good
7,946 reviews

Overall

8.0

Food

7.3

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Crew

8.5

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!
Frontier
6.0
Okay
3,295 reviews
Delta
8.0
Very good
7,946 reviews

Overall

8.0

Food

7.3

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Crew

8.5

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, Frontier ($263), Delta ($477), and American Airlines ($482) offers the cheapest pricing from Cleveland to Simpson Bay. Frontier is priced at 56% 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 $657). 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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$303Average$397FlexibilityNo cancel feeOn-time65%
DeltaCheapest$333Average$587FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$455Average$645FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$457Average$679FlexibilityNo cancel feeOn-time71%

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