Which layover airport offers the lowest fares from Cleveland to Simpson Bay?

Flights via Fort Lauderdale (FLL) offer the lowest average round-trip price of $352.

Which layover airport has the shortest connection time from Cleveland to Simpson Bay?

Washington, D.C. (IAD) has the shortest average layover time for this route: 1h 38m.

What airlines fly to Simpson Bay?

American Airlines, Delta and Spirit Airlines are the top three most popular airlines that fly to Simpson Bay from Cleveland according to our data. American Airlines is the first choice among our users, with 57% of people opting to fly with this airline when traveling to Simpson Bay. Keep in mind that there are 5 different airlines that fly to Simpson Bay on a routine basis, so you have a few additional options to choose from.

Which airport is the most popular layover for flights between Cleveland and Simpson Bay?

Fort Lauderdale (FLL) was the most common stop: 60% of momondo users choosing 1-stop flights on this route connected there.

What is the cheapest airline that flies from Cleveland Hopkins Intl to Simpson Bay Princess Juliana?

Delta, American Airlines, and United Airlines are the most popular carriers operating from Cleveland Hopkins Intl to Simpson Bay Princess Juliana

Which layover airport has the shortest travel time from Cleveland to Simpson Bay?

Flights connecting via Washington, D.C. (IAD) have the shortest average one-way travel time: 6h 50m.

When did momondo last update prices for flights from Cleveland Hopkins Intl Airport to Simpson Bay Princess Juliana Airport?

Prices for flights from Cleveland Hopkins Intl Airport to Simpson Bay Princess Juliana Airport are updated daily.

How many operators does momondo search for flights from Cleveland Hopkins Intl Airport to Simpson Bay Princess Juliana Airport?

The number of operators available for flights from Cleveland Hopkins Intl Airport to Simpson Bay Princess Juliana Airport is 3 as of February 2026.

How old do you have to be to fly from Cleveland Hopkins Intl Airport to Simpson Bay Princess Juliana Airport?

The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Cleveland Hopkins Intl Airport to Simpson Bay Princess Juliana Airport.

What documentation or ID do you need to fly to Simpson Bay Princess Juliana Airport?

The travel and health documents you'll need for your trip to Simpson Bay Princess Juliana Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Simpson Bay Princess Juliana Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

$167 Cheap Flights from Cleveland to Simpson Bay in 2026

Q: What is the typical price of a round-trip flight between Cleveland and Simpson Bay?

Prices are currently low for flights on this route. Typical prices usually range from $451 to $999. The lowest price recently found on this route was $327.

1 adult

0 bags

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Not ready to book? to track prices.

Search flight deals

Find the cheapest flights from Cleveland to Simpson Bay

Round-trip

One-way

Last minute

Cheap round-trip flights

Enter your travel dates to find the best prices.

6:31 pm - 1:15 pm

CLE

SXM

18h 44m

1 stop

2:20 pm - 1:42 am

SXM

CLE

11h 22m

1 stop

$327Multiple Airlines

Sat, Mar 14 - Thu, Mar 19

5:59 pm - 1:15 pm

CLE

SXM

19h 16m

2 stops

2:20 pm - 1:42 am

SXM

CLE

11h 22m

1 stop

$334Multiple Airlines

Sat, Mar 14 - Thu, Mar 19

7:38 pm - 1:30 pm

CLE

SXM

17h 52m

1 stop

2:35 pm - 3:16 pm

SXM

CLE

24h 41m

1 stop

$354Multiple Airlines

Wed, Apr 22 - Mon, May 4

8:15 am - 1:30 pm

CLE

SXM

29h 15m

1 stop

2:35 pm - 3:16 pm

SXM

CLE

24h 41m

1 stop

$361Multiple Airlines

Sat, Apr 25 - Mon, May 4

5:22 pm - 1:30 pm

CLE

SXM

20h 08m

1 stop

12:25 pm - 10:03 am

SXM

CLE

21h 38m

2 stops

$365Multiple Airlines

Sat, Apr 11 - Thu, Apr 16

7:38 pm - 1:30 pm

CLE

SXM

17h 52m

1 stop

2:35 pm - 5:55 pm

SXM

CLE

27h 20m

2 stops

$367Multiple Airlines

Wed, Apr 22 - Fri, May 1

8:15 am - 1:30 pm

CLE

SXM

29h 15m

1 stop

2:35 pm - 4:30 pm

SXM

CLE

25h 55m

1 stop

$368Multiple Airlines

Sat, Apr 25 - Mon, May 4

7:38 pm - 1:30 pm

CLE

SXM

17h 52m

1 stop

2:35 pm - 11:55 pm

SXM

CLE

9h 20m

1 stop

$369Multiple Airlines

Wed, Apr 22 - Fri, May 1

8:15 am - 1:30 pm

CLE

SXM

29h 15m

1 stop

2:35 pm - 5:55 pm

SXM

CLE

27h 20m

2 stops

$374Multiple Airlines

Sat, Apr 25 - Fri, May 1

7:38 pm - 1:30 pm

CLE

SXM

17h 52m

1 stop

2:35 pm - 10:43 am

SXM

CLE

20h 08m

2 stops

$376Multiple Airlines

Wed, Apr 22 - Thu, May 7

American Airlines flights from Cleveland to Simpson Bay

Our best American Airlines deals on Cleveland to Simpson Bay flight tickets

American Airlines

Jun 29

CLE7:39 pmCleveland Hopkins Intl

17h 04m

1 stop

SXM12:43 pmSimpson Bay Princess Juliana

Jul 6

SXM1:45 pmSimpson Bay Princess Juliana

9h 56m

1 stop

CLE11:41 pmCleveland Hopkins Intl

$423

American Airlines

Jun 29

CLE7:29 pmCleveland Hopkins Intl

17h 57m

2 stops

SXM1:26 pmSimpson Bay Princess Juliana

Jul 6

SXM1:45 pmSimpson Bay Princess Juliana

9h 56m

1 stop

CLE11:41 pmCleveland Hopkins Intl

$428

American Airlines

May 14

CLE7:15 pmCleveland Hopkins Intl

18h 05m

2 stops

SXM1:20 pmSimpson Bay Princess Juliana

May 17

SXM12:41 pmSimpson Bay Princess Juliana

20h 34m

2 stops

CLE9:15 amCleveland Hopkins Intl

$433

Air Canada flights from Cleveland to Simpson Bay

Our best Air Canada deals on Cleveland to Simpson Bay flight tickets

Air Canada

Apr 3

CLE6:10 pmCleveland Hopkins Intl

19h 25m

2 stops

SXM1:35 pmSimpson Bay Princess Juliana

Apr 6

SXM4:00 pmSimpson Bay Princess Juliana

25h 30m

1 stop

CLE5:30 pmCleveland Hopkins Intl

$412

Air Canada

Mar 1

CLE6:10 pmCleveland Hopkins Intl

20h 50m

1 stop

SXM4:00 pmSimpson Bay Princess Juliana

Mar 5

SXM3:40 pmSimpson Bay Princess Juliana

26h 50m

2 stops

CLE5:30 pmCleveland Hopkins Intl

$429

Air Canada

Mar 1

CLE6:10 pmCleveland Hopkins Intl

43h 30m

2 stops

SXM2:40 pmSimpson Bay Princess Juliana

Mar 5

SXM3:40 pmSimpson Bay Princess Juliana

26h 50m

2 stops

CLE5:30 pmCleveland Hopkins Intl

$643

Fly from

Fly to

Route

Depart

Return

Price

ClevelandSimpson Bay

CLE - SXM

CLESXM

Cleveland Hopkins Intl

Sat 3/14

6:31 pm-1:15 pm

1 stop18h 44m

Simpson Bay Princess Juliana

Thu 3/19

2:20 pm-1:42 am

1 stop11h 22m

$327

ClevelandSimpson Bay

CLE - SXM

CLESXM

Cleveland Hopkins Intl

Sat 3/14

5:59 pm-1:15 pm

2 stops19h 16m

Simpson Bay Princess Juliana

Thu 3/19

2:20 pm-1:42 am

1 stop11h 22m

$334

ClevelandSimpson Bay

CLE - SXM

CLESXM

Cleveland Hopkins Intl

Wed 4/22

7:38 pm-1:30 pm

1 stop17h 52m

Simpson Bay Princess Juliana

Mon 5/4

2:35 pm-3:16 pm

1 stop24h 41m

$354

ClevelandSimpson Bay

CLE - SXM

CLESXM

Cleveland Hopkins Intl

Sat 4/25

8:15 am-1:30 pm

1 stop29h 15m

Simpson Bay Princess Juliana

Mon 5/4

2:35 pm-3:16 pm

1 stop24h 41m

$361

ClevelandSimpson Bay

CLE - SXM

CLESXM

Cleveland Hopkins Intl

Sat 4/11

5:22 pm-1:30 pm

1 stop20h 08m

Simpson Bay Princess Juliana

Thu 4/16

12:25 pm-10:03 am

2 stops21h 38m

$365

ClevelandSimpson Bay

CLE - SXM

CLESXM

Cleveland Hopkins Intl

Wed 4/22

7:38 pm-1:30 pm

1 stop17h 52m

Simpson Bay Princess Juliana

Fri 5/1

2:35 pm-5:55 pm

2 stops27h 20m

$367

ClevelandSimpson Bay

CLE - SXM

CLESXM

Cleveland Hopkins Intl

Sat 4/25

8:15 am-1:30 pm

1 stop29h 15m

Simpson Bay Princess Juliana

Mon 5/4

2:35 pm-4:30 pm

1 stop25h 55m

$368

ClevelandSimpson Bay

CLE - SXM

CLESXM

Cleveland Hopkins Intl

Wed 4/22

7:38 pm-1:30 pm

1 stop17h 52m

Simpson Bay Princess Juliana

Fri 5/1

2:35 pm-11:55 pm

1 stop9h 20m

$369

ClevelandSimpson Bay

CLE - SXM

CLESXM

Cleveland Hopkins Intl

Sat 4/25

8:15 am-1:30 pm

1 stop29h 15m

Simpson Bay Princess Juliana

Fri 5/1

2:35 pm-5:55 pm

2 stops27h 20m

$374

ClevelandSimpson Bay

CLE - SXM

CLESXM

Cleveland Hopkins Intl

Wed 4/22

7:38 pm-1:30 pm

1 stop17h 52m

Simpson Bay Princess Juliana

Thu 5/7

2:35 pm-10:43 am

2 stops20h 08m

$376

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 16 resultsSorted by cheapest first

How to get the cheapest flight ticket from Cleveland to Simpson Bay

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Prices

Airlines

Layovers

What is the typical price of a round-trip flight between Cleveland and Simpson Bay?

What is the cheapest month to fly to Simpson Bay?

In general, May is the cheapest month to fly from Cleveland to Simpson Bay. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $567. If you aren’t able to travel to Simpson Bay during the month of May, then flying in September is also cheap. Prices for this month can be found on momondo for an average of $575.

How far in advance should I book a flight to Simpson Bay?

You are more likely to see cheaper flights to Simpson Bay from Cleveland when booking weeks ahead of your departure date. In general, you can expect to find flights to Simpson Bay for around $674 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Simpson Bay from Cleveland for as low as $568 on momondo.

When to book flights from Cleveland to Simpson Bay

Are you open to changing your travel dates? Check out the ideal times to fly from Cleveland to Simpson Bay according to our flight data. Find out which month and days have the cheapest flights.

Estimated round-trip price

Cheap Cleveland to Simpson Bay (CLE to SXM) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Cleveland to Simpson Bay

Fastest flight time	6h 33m
Direct flights	None

The fastest flight from Cleveland to Simpson Bay takes 6h 33m

There are no direct flights from Cleveland to Simpson Bay. There are no popular flight routes from Cleveland to Simpson Bay.

Search flight deals

How far is Cleveland Hopkins Intl to Simpson Bay Princess Juliana by plane?
Simpson Bay Princess Juliana is 1956.1 mi away from Cleveland Hopkins Intl. Flights usually cover this in 6h 33m, depending on flying conditions and air traffic around both airports.
When did momondo last update prices for flights from Cleveland Hopkins Intl Airport to Simpson Bay Princess Juliana Airport?
Prices for flights from Cleveland Hopkins Intl Airport to Simpson Bay Princess Juliana Airport are updated daily.
How many operators does momondo search for flights from Cleveland Hopkins Intl Airport to Simpson Bay Princess Juliana Airport?
The number of operators available for flights from Cleveland Hopkins Intl Airport to Simpson Bay Princess Juliana Airport is 3 as of February 2026.
How old do you have to be to fly from Cleveland Hopkins Intl Airport to Simpson Bay Princess Juliana Airport?
The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Cleveland Hopkins Intl Airport to Simpson Bay Princess Juliana Airport.
What documentation or ID do you need to fly to Simpson Bay Princess Juliana Airport?
The travel and health documents you'll need for your trip to Simpson Bay Princess Juliana Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Simpson Bay Princess Juliana Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.
What is the most popular airline from Cleveland to Simpson Bay?
Based on momondo bookings for this flight route, the most popular airline on flight routes from Cleveland to Simpson Bay is American Airlines (62% of total bookings). The next most popular airlines are Delta (31%) and United Airlines (7%).

Best airlines flying from Cleveland to Simpson Bay

Compare and see reviews for airlines that fly from Cleveland to Simpson Bay with momondo

Airline	Rating	Free Cancellation	Price
Delta	PriceFrom $465	Free Cancellation	Rating 7.9 8,237 reviews	Search Delta flights
United Airlines	PriceFrom $488	Free Cancellation	Rating 7.4 9,348 reviews	Search United Airlines flights
American Airlines	PriceFrom $499	Free Cancellation	Rating 7.2 11,352 reviews	Search American Airlines flights

Philipsburg

Why use momondo?

Why should I use momondo to find a flight deal from Cleveland to Simpson Bay?

It is quick and easy to find Cleveland to Simpson Bay flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Simpson Bay that suits you.

Can I find flights from Cleveland to Simpson Bay with flexible booking policies on momondo?

All flight searches from Cleveland to Simpson Bay on momondo can be filtered to show those which offer flexible booking policies.

How can momondo help me find flights from Cleveland to Simpson Bay?

Once you have performed a search for Cleveland to Simpson Bay flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

I’m not ready to book a flight from Cleveland to Simpson Bay right now. Can momondo alert me if prices change?

Price alerts on flights to Simpson Bay from Cleveland are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

An easier way to manage your Simpson Bay trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Start using Trips

Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

1 adult

Sat 3/28

Sat 4/4

Email me momondo's favorite deals

By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to St. Maarten

Airlines

Cabin classes

Other flights from Cleveland

Complete your trip

Feeling lucky

Fly your favorite airline to Simpson Bay

Cheap flights from Cleveland to Simpson Bay from $167

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Cleveland to Simpson Bay departing on 3/18. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

Big names and deals

Big names and deals

Filter for what you want

Filter for what you want

Trusted and free

Trusted and free

Price Alerts

Price Alerts

Find the cheapest flights from Cleveland to Simpson Bay

Cheap round-trip flights

Cheap one-way flights

Cheap last minute flights

American Airlines flights from Cleveland to Simpson Bay

Our best American Airlines deals on Cleveland to Simpson Bay flight tickets

Air Canada flights from Cleveland to Simpson Bay

Our best Air Canada deals on Cleveland to Simpson Bay flight tickets

momondo Fare Finder

Use the filters below to find and compare flights from Cleveland to Simpson Bay that are best for you.

See travel insights to Simpson Bay from

How to get the cheapest flight ticket from Cleveland to Simpson Bay

What is the typical price of a round-trip flight between Cleveland and Simpson Bay?

What is the cheapest month to fly to Simpson Bay?

How far in advance should I book a flight to Simpson Bay?

What is the cheapest airline that flies from Cleveland Hopkins Intl to Simpson Bay Princess Juliana?

What airlines fly to Simpson Bay?

Which airport is the most popular layover for flights between Cleveland and Simpson Bay?

Which layover airport offers the lowest fares from Cleveland to Simpson Bay?

Which layover airport has the shortest travel time from Cleveland to Simpson Bay?

Which layover airport has the shortest connection time from Cleveland to Simpson Bay?

When to book flights from Cleveland to Simpson Bay

Cheap Cleveland to Simpson Bay (CLE to SXM) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Cleveland to Simpson Bay

Fastest flight time

Direct flights

Best airlines flying from Cleveland to Simpson Bay

Compare and see reviews for airlines that fly from Cleveland to Simpson Bay with momondo

Traveling to a place near Simpson Bay?

Why use momondo?

An easier way to manage your Simpson Bay trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to St. Maarten

Fly your favorite airline to Simpson Bay

Airlines are sorted and displayed according to clicks in the past 7 days on momondo

Cabin classes currently available on flights to Simpson Bay

List of cabin classes available on flights landing in Simpson Bay. Availability may vary depending on flight origin and airline.

Fly to other destinations from Cleveland

According to popular flight searches on momondo this year

Complete your trip to Simpson Bay

Explore popular destinations other users love

According to popular flight searches on momondo this year