HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Simpson Bay

$354+ 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 5/18. Fares are subject to change and may not be available on all flights or dates of travel.
CLE — SXM
May 6 — May 131
Tue 5/6
Tue 5/13
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

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 May 1, 2025.

Most accurate provider

AranGrant
3 stars

Most trusted provider

AranGrant
3 stars

Round-trip from

$364
(Booking.com)

Popular in

January

Cheapest in

September

Average price

$567
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
Highest demand for flights based on searches. 4% potential increase in price ($30 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($9 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2025
Search Deals

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 May 1, 2025.

This Flightnetwork deal was found by Cheapflights users on 4/30. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/189:30 pmCLE - SXM
1 stop19h 31mFrontier
Sat 5/2412:34 pmSXM - CLE
1 stop10h 53mFrontier
Deal found 4/30$354
This Kiwi.com deal was found by Cheapflights users on 4/30. 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.
Thu 6/124:21 pmCLE - SXM
1 stop21h 39mMultiple Airlines
Sun 6/159:14 amSXM - CLE
2 stops24h 34mMultiple Airlines
Deal found 4/30$506
This Delta deal was found by Cheapflights users on 4/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/157:05 amCLE - SXM
1 stop6h 51mDelta
Tue 7/293:21 pmSXM - CLE
1 stop9h 32mDelta
Deal found 4/29$537
This American Airlines deal was found by Cheapflights users on 4/30. 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 7/158:00 pmCLE - SXM
2 stops19h 05mAmerican Airlines
Tue 7/292:45 pmSXM - CLE
1 stop9h 28mAmerican Airlines
Deal found 4/30$542
This Mytrip deal was found by Cheapflights users on 4/30. 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.
Sun 5/185:41 pmCLE - SXM
3 stops20h 19mSpirit Airlines
Sat 5/243:05 pmSXM - CLE
3 stops25h 31mSpirit Airlines
Deal found 4/30$563
This WestJet deal was found by Cheapflights users on 4/29. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/295:30 amCLE - SXM
2 stops32h 47mWestJet
Fri 11/144:10 pmSXM - CLE
2 stops22h 25mWestJet
Deal found 4/29$4,647

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 May 1, 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

Sun 5/18

9:30 pm-5:01 pm

1 stop19h 31m

Simpson Bay Princess Juliana

Sat 5/24

12:34 pm-11:27 pm

1 stop10h 53m

$354

ClevelandSimpson Bay

CLE - SXM

CLESXM

Cleveland Hopkins Intl

Thu 6/12

4:21 pm-2:00 pm

1 stop21h 39m

Simpson Bay Princess Juliana

Sun 6/15

9:14 am-9:48 am

2 stops24h 34m

$506

ClevelandSimpson Bay

CLE - SXM

CLESXM

Cleveland Hopkins Intl

Tue 7/15

7:05 am-1:56 pm

1 stop6h 51m

Simpson Bay Princess Juliana

Tue 7/29

3:21 pm-12:53 am

1 stop9h 32m

$537

ClevelandSimpson Bay

CLE - SXM

CLESXM

Cleveland Hopkins Intl

Tue 7/15

8:00 pm-3:05 pm

2 stops19h 05m

Simpson Bay Princess Juliana

Tue 7/29

2:45 pm-12:13 am

1 stop9h 28m

$542

ClevelandSimpson Bay

CLE - SXM

CLESXM

Cleveland Hopkins Intl

Sun 5/18

5:41 pm-2:00 pm

3 stops20h 19m

Simpson Bay Princess Juliana

Sat 5/24

3:05 pm-4:36 pm

3 stops25h 31m

$563

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/30

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 May.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*2 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy3 starsTrust Score*3 stars
CheapflightsfaresPrice Accuracy3 starsTrust Score*2 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 AranGrant to be most consistent on Cheapflights vs. AranGrant Users can find the same prices on Cleveland-Simpson Bay flight deals on Cheapflights vs. AranGrant >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 AranGrant the most. AranGrant 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 April 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 July is currently the most expensive (average of $669). 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.

What is the cheapest time of day to fly from CLE to SXM?

Find hourly flight availability from Cleveland to Simpson Bay. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated May 1, 2025.

A simple way to save on the total cost of your ticket is to fly from Cleveland to Simpson Bay at noon. If you’re flexible enough to do this you can expect to save up to 21% on your trip compared to booking a flight in the morning.

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 May 1, 2025.
Read through reviews of airlines operating flights from Cleveland to Simpson Bay, such as Delta, American Airlines and Frontier. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,934 reviews

Overall

8.0

Entertainment

7.9

Crew

8.5

Boarding

8.2

Food

7.3

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Delta
8.0
Very good
7,934 reviews
Delta
8.0
Very good
7,934 reviews

Overall

8.0

Entertainment

7.9

Crew

8.5

Boarding

8.2

Food

7.3

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,934 reviews

Overall

8.0

Entertainment

7.9

Crew

8.5

Boarding

8.2

Food

7.3

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Frontier
6.0
Okay
3,287 reviews
Delta
8.0
Very good
7,934 reviews

Overall

8.0

Entertainment

7.9

Crew

8.5

Boarding

8.2

Food

7.3

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

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 ($364), Delta ($537), and American Airlines ($542) offers the cheapest pricing from Cleveland to Simpson Bay. Frontier is priced at 39% 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 July is currently the most expensive (average of $669). 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

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 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 May 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$269Average$410FlexibilityNo cancel feeOn-time65%
DeltaCheapest$333Average$589FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$455Average$645FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$456Average$657FlexibilityNo 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.