HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Simpson Bay

$101+ 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 1/22. Fares are subject to change and may not be available on all flights or dates of travel.
CLE — SXM
jan 8 — jan 151
qui 1/8
qui 1/15
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Cleveland to Simpson Bay with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 dezembro 9, 2025.

This Kiwi.com deal was found by Cheapflights users on 12/9. 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.
ter 12/305:06 pmCLE - SXM
1 stop20h 09mMultiple Airlines
qui 1/111:30 amSXM - CLE
2 stops14h 06mMultiple Airlines
Deal found 12/9$617
This FlightHub deal was found by Cheapflights users on 12/8. 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.
seg 12/226:10 pmCLE - SXM
1 stop20h 50mMultiple Airlines
seg 12/293:45 pmSXM - CLE
2 stops32h 55mMultiple Airlines
Deal found 12/8$623
This Kiwi.com deal was found by Cheapflights users on 12/9. 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.
ter 12/306:00 amCLE - SXM
2 stops31h 15mMultiple Airlines
sex 1/23:20 pmSXM - CLE
1 stop20h 17mMultiple Airlines
Deal found 12/9$672
This Delta deal was found by Cheapflights users on 12/7. 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.
qua 12/246:05 amCLE - SXM
1 stop7h 45mDelta
ter 12/301:45 pmSXM - CLE
1 stop9h 54mDelta
Deal found 12/7$712
This American Airlines deal was found by Cheapflights users on 12/7. 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.
seg 12/227:05 pmCLE - SXM
1 stop16h 31mAmerican Airlines
seg 12/291:39 pmSXM - CLE
1 stop11h 20mAmerican Airlines
Deal found 12/7$722
This American Airlines deal was found by Cheapflights users on 12/7. 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.
qua 12/245:30 amCLE - SXM
1 stop6h 56mAmerican Airlines
ter 12/301:39 pmSXM - CLE
2 stops11h 46mAmerican Airlines
Deal found 12/7$734
This Priceline deal was found by Cheapflights users on 12/7. 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.
sex 12/266:30 amCLE - SXM
1 stop30h 00mMultiple Airlines
qui 1/12:26 pmSXM - CLE
2 stops34h 14mMultiple Airlines
Deal found 12/7$736
This Kiwi.com deal was found by Cheapflights users on 12/9. 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.
dom 12/282:05 pmCLE - SXM
1 stop23h 10mMultiple Airlines
qui 1/111:30 amSXM - CLE
2 stops14h 06mMultiple Airlines
Deal found 12/9$746
This FlightHub deal was found by Cheapflights users on 12/7. 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.
qua 12/246:10 pmCLE - SXM
2 stops19h 30mMultiple Airlines
ter 12/302:26 pmSXM - CLE
2 stops29h 49mMultiple Airlines
Deal found 12/7$777
This Kiwi.com deal was found by Cheapflights users on 12/9. 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.
dom 12/282:05 pmCLE - SXM
1 stop23h 10mMultiple Airlines
sex 1/23:20 pmSXM - CLE
2 stops41h 23mMultiple Airlines
Deal found 12/9$795

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 dezembro 9, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$261
(Kiwi.com)

One-way from

$145
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$793
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.
Search Deals
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. 8% potential increase in price ($64 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($11 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
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 dezembro 9, 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

qua 2/18

8:00 pm-2:10 pm

1 stop17h 10m

Simpson Bay Princess Juliana

ter 2/24

3:15 pm-9:58 am

1 stop19h 43m

$261

ClevelandSimpson Bay

CLE - SXM

CLESXM

Cleveland Hopkins Intl

qui 1/22

3:44 pm-2:10 pm

1 stop21h 26m

Simpson Bay Princess Juliana

seg 1/26

3:15 pm-7:34 am

2 stops17h 19m

$303

ClevelandSimpson Bay

CLE - SXM

CLESXM

Cleveland Hopkins Intl

qui 1/22

3:44 pm-2:10 pm

1 stop21h 26m

Simpson Bay Princess Juliana

dom 1/25

3:15 pm-6:06 pm

1 stop27h 51m

$304

ClevelandSimpson Bay

CLE - SXM

CLESXM

Cleveland Hopkins Intl

ter 2/24

8:00 pm-2:10 pm

1 stop17h 10m

Simpson Bay Princess Juliana

sáb 2/28

3:15 pm-10:33 pm

1 stop8h 18m

$321

ClevelandSimpson Bay

CLE - SXM

CLESXM

Cleveland Hopkins Intl

sáb 1/31

4:19 pm-2:10 pm

1 stop20h 51m

Simpson Bay Princess Juliana

sáb 2/7

3:15 pm-11:11 pm

2 stops32h 56m

$335

ClevelandSimpson Bay

CLE - SXM

CLESXM

Cleveland Hopkins Intl

sex 1/23

3:44 pm-2:10 pm

1 stop21h 26m

Simpson Bay Princess Juliana

sáb 1/31

3:15 pm-7:34 am

2 stops17h 19m

$343

ClevelandSimpson Bay

CLE - SXM

CLESXM

Cleveland Hopkins Intl

qua 1/21

3:59 pm-2:10 pm

1 stop21h 11m

Simpson Bay Princess Juliana

qua 1/28

9:35 am-10:59 pm

2 stops14h 24m

$402

ClevelandSimpson Bay

CLE - SXM

CLESXM

Cleveland Hopkins Intl

dom 3/1

6:10 pm-4:00 pm

1 stop20h 50m

Simpson Bay Princess Juliana

sáb 3/7

4:40 pm-4:13 pm

1 stop24h 33m

$415

ClevelandSimpson Bay

CLE - SXM

CLESXM

Cleveland Hopkins Intl

sáb 2/7

4:19 pm-2:10 pm

1 stop20h 51m

Simpson Bay Princess Juliana

sex 2/13

3:15 pm-5:20 pm

1 stop27h 05m

$420

ClevelandSimpson Bay

CLE - SXM

CLESXM

Cleveland Hopkins Intl

qui 1/22

3:44 pm-2:10 pm

1 stop21h 26m

$101

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/9

Showing 1-10 of 18 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 December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy2 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 eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Cleveland-Simpson Bay flight deals on Cheapflights vs. eDreams >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 eDreams the most. eDreams 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 December 5, 2025.

The best time to book flights from Cleveland to Simpson Bay is 72 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 $192). 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.

How much does it cost to fly round-trip from Cleveland to Simpson Bay?

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 dezembro 9, 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
7.9
Good
8,011 reviews

Crew

8.5

Comfort

7.9

Food

7.3

Entertainment

7.9

Overall

7.9

Boarding

8.1

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
8,011 reviews
Delta
7.9
Good
8,011 reviews

Crew

8.5

Comfort

7.9

Food

7.3

Entertainment

7.9

Overall

7.9

Boarding

8.1

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
9,089 reviews
Delta
7.9
Good
8,011 reviews

Crew

8.5

Comfort

7.9

Food

7.3

Entertainment

7.9

Overall

7.9

Boarding

8.1

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
11,045 reviews
Delta
7.9
Good
8,011 reviews

Crew

8.5

Comfort

7.9

Food

7.3

Entertainment

7.9

Overall

7.9

Boarding

8.1

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.

  • 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 ($537) offers the cheapest pricing from Cleveland to Simpson Bay. United Airlines is priced at 32% 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 $192). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 dezembro 9, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$455Average$677FlexibilityNo cancel feeOn-time69%
DeltaCheapest$460Average$663FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$537Average$708FlexibilityNo cancel feeOn-time71%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.