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Simpson Bay

$372+ 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 12/6. Fares are subject to change and may not be available on all flights or dates of travel.
CLE — SXM
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
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 September 11, 2025.

Round-trip from

$372
(Expedia)

Popular in

December

Cheapest in

November

Average price

$582
From Cleveland Hopkins Intl to Simpson Bay Princess Juliana
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Highest demand for flights based on searches. 0% potential increase in price ($6 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($12 potential savings vs. average RT price).
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Average for round-trip flights in September 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 September 11, 2025.

This Expedia deal was found by Cheapflights users on 9/11. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/65:30 amCLE - SXM
1 stop8h 50mFrontier
Sat 12/134:30 pmSXM - CLE
1 stop19h 03mFrontier
Deal found 9/11$372
This FlightHub deal was found by Cheapflights users on 9/10. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/56:15 pmCLE - SXM
2 stops19h 25mMultiple Airlines
Sat 12/134:30 pmSXM - CLE
1 stop19h 03mMultiple Airlines
Deal found 9/10$421
This Priceline deal was found by Cheapflights users on 9/11. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/65:30 amCLE - SXM
1 stop8h 50mMultiple Airlines
Sat 12/133:40 pmSXM - CLE
2 stops26h 59mMultiple Airlines
Deal found 9/11$424
This American Airlines deal was found by Cheapflights users on 9/11. 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.
Sat 11/298:50 pmCLE - SXM
2 stops18h 32mAmerican Airlines
Fri 12/55:25 pmSXM - CLE
2 stops19h 55mAmerican Airlines
Deal found 9/11$466
This Air Canada deal was found by Cheapflights users on 9/10. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/56:15 pmCLE - SXM
2 stops19h 25mAir Canada
Sat 12/133:40 pmSXM - CLE
2 stops26h 59mAir Canada
Deal found 9/10$473
This American Airlines deal was found by Cheapflights users on 9/10. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/316:04 amCLE - SXM
1 stop9h 11mAmerican Airlines
Fri 11/72:51 pmSXM - CLE
1 stop7h 45mAmerican Airlines
Deal found 9/10$486
This American Airlines deal was found by Cheapflights users on 9/10. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/298:50 pmCLE - SXM
2 stops18h 32mAmerican Airlines
Sat 12/64:00 pmSXM - CLE
1 stop18h 32mAmerican Airlines
Deal found 9/10$491
This American Airlines deal was found by Cheapflights users on 9/10. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/184:34 pmCLE - SXM
2 stops20h 16mAmerican Airlines
Sun 11/235:24 pmSXM - CLE
2 stops18h 01mAmerican Airlines
Deal found 9/10$496
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/256:27 pmCLE - SXM
2 stops40h 23mMultiple Airlines
Sat 11/13:05 pmSXM - CLE
1 stop8h 06mMultiple Airlines
Deal found 9/10$539
This American Airlines deal was found by Cheapflights users on 9/10. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/253:36 pmCLE - SXM
2 stops22h 06mAmerican Airlines
Sat 11/12:40 pmSXM - CLE
2 stops19h 32mAmerican Airlines
Deal found 9/10$587

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 September 11, 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

Sat 12/6

5:30 am-3:20 pm

1 stop8h 50m

Simpson Bay Princess Juliana

Sat 12/13

3:40 pm-5:39 pm

2 stops26h 59m

$424

ClevelandSimpson Bay

CLE - SXM

CLESXM

Cleveland Hopkins Intl

Sat 11/29

8:50 pm-4:22 pm

2 stops18h 32m

Simpson Bay Princess Juliana

Fri 12/5

5:25 pm-12:20 pm

2 stops19h 55m

$466

ClevelandSimpson Bay

CLE - SXM

CLESXM

Cleveland Hopkins Intl

Fri 12/5

6:15 pm-2:40 pm

2 stops19h 25m

Simpson Bay Princess Juliana

Sat 12/13

3:40 pm-5:39 pm

2 stops26h 59m

$473

ClevelandSimpson Bay

CLE - SXM

CLESXM

Cleveland Hopkins Intl

Tue 11/18

6:06 am-4:22 pm

1 stop9h 16m

Simpson Bay Princess Juliana

Sun 11/23

3:20 pm-11:53 pm

1 stop9h 33m

$491

ClevelandSimpson Bay

CLE - SXM

CLESXM

Cleveland Hopkins Intl

Sat 11/29

8:50 pm-4:22 pm

2 stops18h 32m

Simpson Bay Princess Juliana

Sat 12/6

5:25 pm-9:32 am

2 stops17h 07m

$491

ClevelandSimpson Bay

CLE - SXM

CLESXM

Cleveland Hopkins Intl

Fri 10/31

6:04 am-3:15 pm

1 stop9h 11m

Simpson Bay Princess Juliana

Fri 11/7

3:20 pm-8:47 am

2 stops18h 27m

$491

ClevelandSimpson Bay

CLE - SXM

CLESXM

Cleveland Hopkins Intl

Sat 12/6

4:25 pm-2:20 pm

2 stops20h 55m

Simpson Bay Princess Juliana

Sat 12/13

5:25 pm-9:32 am

2 stops17h 07m

$491

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/11

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 August 29, 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 $652). 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 September 11, 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
8.0
Very good
7,960 reviews

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Food

7.3

Crew

8.5

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
7,960 reviews
Delta
8.0
Very good
7,960 reviews

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Food

7.3

Crew

8.5

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
8,937 reviews
Delta
8.0
Very good
7,960 reviews

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Food

7.3

Crew

8.5

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
7,960 reviews

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Food

7.3

Crew

8.5

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.

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

    For as low as $466, American Airlines can have you in Simpson Bay from Cleveland in 18h 32m. 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 ($505) offers the cheapest pricing from Cleveland to Simpson Bay. United Airlines is priced at 29% 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 $652). 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 September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$455Average$635FlexibilityNo cancel feeOn-time69%
DeltaCheapest$460Average$619FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$505Average$689FlexibilityNo cancel feeOn-time71%

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