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

Atlanta (ATL) was the most common stop: 33% of momondo users choosing 1-stop flights on this route connected there.

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

Flights via Washington, D.C. (IAD) offer the lowest average round-trip price of $447.

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

Air Canada and American 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.

What airlines fly to Simpson Bay?

American Airlines, JetBlue and United 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 53% 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.

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 4 as of September 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.

$133 Cheap Flights from Cleveland to Simpson Bay in 2026/27

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Cleveland to Simpson Bay

Round-trip

One-way

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Enter your travel dates to find the best prices.

6:55 pm - 3:45 pmCLE Cleveland Hopkins Intl-SXM Simpson Bay Princess Juliana

19h 50m1 stop Toronto Pearson Intl

4:45 pm - 6:17 pmSXM Simpson Bay Princess Juliana-CLE Cleveland Hopkins Intl

26h 32m1 stop Toronto Pearson Intl

$357Air Canada

Sun, Nov 1 - Sun, Nov 8

6:55 pm - 3:45 pmCLE Cleveland Hopkins Intl-SXM Simpson Bay Princess Juliana

19h 50m1 stop Toronto Pearson Intl

4:45 pm - 6:17 pmSXM Simpson Bay Princess Juliana-CLE Cleveland Hopkins Intl

26h 32m1 stop Toronto Pearson Intl

$361Air Canada

Sun, Nov 15 - Fri, Nov 20

6:00 am - 2:15 pmCLE Cleveland Hopkins Intl-SXM Simpson Bay Princess Juliana

7h 15m1 stop Miami

2:55 pm - 10:53 pmSXM Simpson Bay Princess Juliana-CLE Cleveland Hopkins Intl

8h 58m1 stop Philadelphia

$447American Airlines

Thu, Nov 26 - Sat, Dec 5

7:05 am - 2:40 pmCLE Cleveland Hopkins Intl-SXM Simpson Bay Princess Juliana

6h 35m1 stop Atlanta Hartsfield-Jackson

4:05 pm - 12:56 amSXM Simpson Bay Princess Juliana-CLE Cleveland Hopkins Intl

9h 51m1 stop Atlanta Hartsfield-Jackson

$447Delta

Mon, Nov 16 - Fri, Nov 20

7:05 am - 2:40 pmCLE Cleveland Hopkins Intl-SXM Simpson Bay Princess Juliana

6h 35m1 stop Atlanta Hartsfield-Jackson

4:05 pm - 12:56 amSXM Simpson Bay Princess Juliana-CLE Cleveland Hopkins Intl

9h 51m1 stop Atlanta Hartsfield-Jackson

$447Delta

Tue, Nov 17 - Thu, Nov 19

6:51 pm - 1:26 pmCLE Cleveland Hopkins Intl-SXM Simpson Bay Princess Juliana

17h 35m1 stop Charlotte Douglas

3:26 pm - 10:55 pmSXM Simpson Bay Princess Juliana-CLE Cleveland Hopkins Intl

8h 29m1 stop Miami

$450American Airlines

Tue, Nov 3 - Sat, Nov 7

4:04 pm - 12:50 pmCLE Cleveland Hopkins Intl-SXM Simpson Bay Princess Juliana

20h 46m1 stop Newark

1:52 pm - 9:33 amSXM Simpson Bay Princess Juliana-CLE Cleveland Hopkins Intl

19h 41m1 stop Newark

$589United Airlines

Sun, Oct 25 - Thu, Oct 29

4:04 pm - 12:50 pmCLE Cleveland Hopkins Intl-SXM Simpson Bay Princess Juliana

20h 46m1 stop Newark

1:52 pm - 9:33 amSXM Simpson Bay Princess Juliana-CLE Cleveland Hopkins Intl

19h 41m1 stop Newark

$600United Airlines

Sun, Oct 25 - Thu, Oct 29

7:00 am - 4:34 pmCLE Cleveland Hopkins Intl-SXM Simpson Bay Princess Juliana

8h 34m1 stop Boston Logan Intl

2:15 pm - 11:49 pmSXM Simpson Bay Princess Juliana-CLE Cleveland Hopkins Intl

10h 34m1 stop Fort Lauderdale

$1,767JetBlue

Sat, Nov 21 - Fri, Nov 27

8:00 am - 2:55 pmCLE Cleveland Hopkins Intl-SXM Simpson Bay Princess Juliana

29h 55m1 stop Fort Lauderdale

2:20 pm - 11:49 pmSXM Simpson Bay Princess Juliana-CLE Cleveland Hopkins Intl

10h 29m1 stop Fort Lauderdale

$11,193JetBlue

Fri, Nov 13 - Sat, Nov 21

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American Airlines flights from Cleveland to Simpson Bay

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

American Airlines

Nov 3

CLE6:51 pmCleveland Hopkins Intl

17h 35m

1 stop

SXM1:26 pmSimpson Bay Princess Juliana

Nov 7

SXM3:26 pmSimpson Bay Princess Juliana

8h 29m

1 stop

CLE10:55 pmCleveland Hopkins Intl

$450

American Airlines

Nov 14

CLE6:52 pmCleveland Hopkins Intl

18h 34m

2 stops

SXM2:26 pmSimpson Bay Princess Juliana

Nov 21

SXM5:29 pmSimpson Bay Princess Juliana

16h 54m

2 stops

CLE9:23 amCleveland Hopkins Intl

$452

American Airlines

Jan 9

CLE6:42 pmCleveland Hopkins Intl

16h 44m

1 stop

SXM12:26 pmSimpson Bay Princess Juliana

Jan 16

SXM1:01 pmSimpson Bay Princess Juliana

11h 37m

1 stop

CLE11:38 pmCleveland Hopkins Intl

$454

Air Canada flights from Cleveland to Simpson Bay

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

Air Canada

Sep 26

CLE10:00 amCleveland Hopkins Intl

7h 00m

1 stop

SXM5:00 pmSimpson Bay Princess Juliana

Oct 3

SXM6:00 pmSimpson Bay Princess Juliana

20h 07m

1 stop

CLE2:07 pmCleveland Hopkins Intl

$329

Air Canada

Nov 1

CLE6:55 pmCleveland Hopkins Intl

19h 50m

1 stop

SXM3:45 pmSimpson Bay Princess Juliana

Nov 8

SXM4:45 pmSimpson Bay Princess Juliana

26h 32m

1 stop

CLE6:17 pmCleveland Hopkins Intl

$357

Air Canada

Nov 14

CLE6:55 pmCleveland Hopkins Intl

19h 50m

1 stop

SXM3:45 pmSimpson Bay Princess Juliana

Nov 20

SXM4:45 pmSimpson Bay Princess Juliana

26h 32m

1 stop

CLE6:17 pmCleveland Hopkins Intl

$361

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ClevelandSimpson Bay

CLE Cleveland Hopkins Intl - SXM Simpson Bay Princess Juliana

CLESXM

Cleveland Hopkins Intl

Sun 11/1

6:55 pm-3:45 pm

1 stop19h 50m

Simpson Bay Princess Juliana

Sun 11/8

4:45 pm-6:17 pm

1 stop26h 32m

$357

ClevelandSimpson Bay

CLE Cleveland Hopkins Intl - SXM Simpson Bay Princess Juliana

CLESXM

Cleveland Hopkins Intl

Sun 11/15

6:55 pm-3:45 pm

1 stop19h 50m

Simpson Bay Princess Juliana

Fri 11/20

4:45 pm-6:17 pm

1 stop26h 32m

$361

Quickest round-trip

ClevelandSimpson Bay

CLE Cleveland Hopkins Intl - SXM Simpson Bay Princess Juliana

CLESXM

Cleveland Hopkins Intl

Thu 11/26

6:00 am-2:15 pm

1 stop7h 15m

Simpson Bay Princess Juliana

Sat 12/5

2:55 pm-10:53 pm

1 stop8h 58m

$447

ClevelandSimpson Bay

CLE Cleveland Hopkins Intl - SXM Simpson Bay Princess Juliana

CLESXM

Cleveland Hopkins Intl

Mon 11/16

7:05 am-2:40 pm

1 stop6h 35m

Simpson Bay Princess Juliana

Fri 11/20

4:05 pm-12:56 am

1 stop9h 51m

$447

ClevelandSimpson Bay

CLE Cleveland Hopkins Intl - SXM Simpson Bay Princess Juliana

CLESXM

Cleveland Hopkins Intl

Tue 11/17

7:05 am-2:40 pm

1 stop6h 35m

Simpson Bay Princess Juliana

Thu 11/19

4:05 pm-12:56 am

1 stop9h 51m

$447

ClevelandSimpson Bay

CLE Cleveland Hopkins Intl - SXM Simpson Bay Princess Juliana

CLESXM

Cleveland Hopkins Intl

Tue 11/3

6:51 pm-1:26 pm

1 stop17h 35m

Simpson Bay Princess Juliana

Sat 11/7

3:26 pm-10:55 pm

1 stop8h 29m

$450

ClevelandSimpson Bay

CLE Cleveland Hopkins Intl - SXM Simpson Bay Princess Juliana

CLESXM

Cleveland Hopkins Intl

Sun 10/25

4:04 pm-12:50 pm

1 stop20h 46m

Simpson Bay Princess Juliana

Thu 10/29

1:52 pm-9:33 am

1 stop19h 41m

$589

ClevelandSimpson Bay

CLE Cleveland Hopkins Intl - SXM Simpson Bay Princess Juliana

CLESXM

Cleveland Hopkins Intl

Sun 10/25

4:04 pm-12:50 pm

1 stop20h 46m

Simpson Bay Princess Juliana

Thu 10/29

1:52 pm-9:33 am

1 stop19h 41m

$600

ClevelandSimpson Bay

CLE Cleveland Hopkins Intl - SXM Simpson Bay Princess Juliana

CLESXM

Cleveland Hopkins Intl

Sat 11/21

7:00 am-4:34 pm

1 stop8h 34m

Simpson Bay Princess Juliana

Fri 11/27

2:15 pm-11:49 pm

1 stop10h 34m

$1,767

ClevelandSimpson Bay

CLE Cleveland Hopkins Intl - SXM Simpson Bay Princess Juliana

CLESXM

Cleveland Hopkins Intl

Fri 11/13

8:00 am-2:55 pm

1 stop29h 55m

Simpson Bay Princess Juliana

Sat 11/21

2:20 pm-11:49 pm

1 stop10h 29m

$11,193

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 13 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 cheapest month to fly to Simpson Bay?

In general, April 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 $499. If you aren’t able to travel to Simpson Bay during the month of April, then flying in July is also cheap. Prices for this month can be found on momondo for an average of $513.

How far in advance should I book a flight from Cleveland 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 $600 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 $509 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

Best Price Found	$133
Fastest flight time	7h 00m
Direct flights	None

The best one-way flight to Simpson Bay from Cleveland in the past 72 hours is $133. The best round-trip flight deal from Cleveland to Simpson Bay found on momondo in the last 72 hours is $357.

The fastest flight from Cleveland to Simpson Bay takes 7h 00m

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

Search flight deals

Frequently asked questions about flying from Cleveland to Simpson Bay

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 7h 00m, 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 4 as of September 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 (64% of total bookings). The next most popular airlines are Delta (17%), United Airlines (12%), and JetBlue (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 $202	Free Cancellation	Rating 7.8 8,585 reviews	Search Delta flights
JetBlue	PriceFrom $276	Free Cancellation	Rating 7.1 3,034 reviews	Search JetBlue flights
American Airlines	PriceFrom $435	Free Cancellation	Rating 7.1 12,077 reviews	Search American Airlines flights
United Airlines	PriceFrom $447	Free Cancellation	Rating 7.4 10,224 reviews	Search United Airlines flights

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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.

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Cheap flights from Cleveland to Simpson Bay from $133

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 12/15. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

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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

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

What is the cheapest month to fly to Simpson Bay?

How far in advance should I book a flight from Cleveland 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

Best Price Found

Fastest flight time

Direct flights

Frequently asked questions about flying from Cleveland to Simpson Bay

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

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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.

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