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 50% 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 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.

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

Miami (MIA) was the most common stop: 40% 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?

JetBlue is the most popular carrier operating from Cleveland Hopkins Intl to Simpson Bay Princess Juliana

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.

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 November 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.

$244 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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Cheap round-trip flights

Enter your travel dates to find the best prices.

6:55 pm - 2:35 pmCLE Cleveland Hopkins Intl-SXM Simpson Bay Princess Juliana

18h 40m2 stops Toronto Pearson Intl Montreal Pierre Elliott Trudeau Intl

4:50 pm - 6:19 pmSXM Simpson Bay Princess Juliana-CLE Cleveland Hopkins Intl

26h 29m1 stop Toronto Pearson Intl

$442Air Canada

Wed, Dec 9 - Wed, Dec 16

6:55 pm - 2:45 pmCLE Cleveland Hopkins Intl-SXM Simpson Bay Princess Juliana

42h 50m2 stops Toronto Pearson Intl Montreal Pierre Elliott Trudeau Intl

4:50 pm - 6:19 pmSXM Simpson Bay Princess Juliana-CLE Cleveland Hopkins Intl

26h 29m1 stop Toronto Pearson Intl

$442Air Canada

Thu, Dec 3 - Mon, Dec 7

6:00 am - 3:11 pmCLE Cleveland Hopkins Intl-SXM Simpson Bay Princess Juliana

8h 11m1 stop New York John F Kennedy Intl

3:30 pm - 10:44 pmSXM Simpson Bay Princess Juliana-CLE Cleveland Hopkins Intl

8h 14m1 stop New York John F Kennedy Intl

$464JetBlue

Thu, Nov 26 - Sat, Dec 5

6:00 am - 4:24 pmCLE Cleveland Hopkins Intl-SXM Simpson Bay Princess Juliana

9h 24m1 stop Miami

4:30 pm - 11:56 pmSXM Simpson Bay Princess Juliana-CLE Cleveland Hopkins Intl

8h 26m1 stop Charlotte Douglas

$487American Airlines

Thu, Nov 26 - Sat, Dec 5

8:09 pm - 1:32 pmCLE Cleveland Hopkins Intl-SXM Simpson Bay Princess Juliana

16h 23m1 stop Charlotte Douglas

3:27 pm - 11:23 pmSXM Simpson Bay Princess Juliana-CLE Cleveland Hopkins Intl

8h 56m1 stop Miami

$487American Airlines

Tue, Dec 1 - Tue, Dec 8

5:45 am - 1:50 pmCLE Cleveland Hopkins Intl-SXM Simpson Bay Princess Juliana

7h 05m1 stop Newark

2:10 pm - 10:22 pmSXM Simpson Bay Princess Juliana-CLE Cleveland Hopkins Intl

9h 12m1 stop Chicago O'Hare Intl

$487United Airlines

Tue, Dec 15 - Tue, Dec 22

6:00 am - 2:40 pmCLE Cleveland Hopkins Intl-SXM Simpson Bay Princess Juliana

7h 40m1 stop Atlanta Hartsfield-Jackson

4:05 pm - 1:07 amSXM Simpson Bay Princess Juliana-CLE Cleveland Hopkins Intl

10h 02m1 stop Atlanta Hartsfield-Jackson

$487Delta

Wed, Dec 9 - Wed, Dec 16

7:43 pm - 1:50 pmCLE Cleveland Hopkins Intl-SXM Simpson Bay Princess Juliana

17h 07m1 stop Washington, D.C. Dulles Intl

5:00 pm - 9:47 amSXM Simpson Bay Princess Juliana-CLE Cleveland Hopkins Intl

17h 47m1 stop Washington, D.C. Dulles Intl

$495United Airlines

Sat, Jan 23 - Sat, Jan 30

6:00 pm - 12:10 pmCLE Cleveland Hopkins Intl-SXM Simpson Bay Princess Juliana

18h 10m1 stop New York John F Kennedy Intl

1:35 pm - 11:06 pmSXM Simpson Bay Princess Juliana-CLE Cleveland Hopkins Intl

9h 31m1 stop Atlanta Hartsfield-Jackson

$495Delta

Mon, Apr 12 - Wed, Apr 14

6:00 am - 3:11 pmCLE Cleveland Hopkins Intl-SXM Simpson Bay Princess Juliana

8h 11m1 stop New York John F Kennedy Intl

1:41 pm - 9:29 pmSXM Simpson Bay Princess Juliana-CLE Cleveland Hopkins Intl

8h 48m1 stop Boston Logan Intl

$510JetBlue

Wed, Dec 16 - Wed, Dec 23

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JetBlue flights from Cleveland to Simpson Bay

Our best JetBlue deals on Cleveland to Simpson Bay flight tickets

JetBlue

Nov 26

CLE6:00 amCleveland Hopkins Intl

8h 11m

1 stop

SXM3:11 pmSimpson Bay Princess Juliana

Dec 5

SXM3:30 pmSimpson Bay Princess Juliana

8h 14m

1 stop

CLE10:44 pmCleveland Hopkins Intl

$464

JetBlue

Dec 16

CLE6:00 amCleveland Hopkins Intl

8h 11m

1 stop

SXM3:11 pmSimpson Bay Princess Juliana

Dec 23

SXM1:41 pmSimpson Bay Princess Juliana

8h 48m

1 stop

CLE9:29 pmCleveland Hopkins Intl

$510

JetBlue

Dec 16

CLE6:00 amCleveland Hopkins Intl

8h 11m

1 stop

SXM3:11 pmSimpson Bay Princess Juliana

Dec 23

SXM1:41 pmSimpson Bay Princess Juliana

8h 48m

1 stop

CLE9:29 pmCleveland Hopkins Intl

$517

American Airlines flights from Cleveland to Simpson Bay

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

American Airlines

Nov 26

CLE6:00 amCleveland Hopkins Intl

9h 24m

1 stop

SXM4:24 pmSimpson Bay Princess Juliana

Dec 5

SXM4:30 pmSimpson Bay Princess Juliana

8h 26m

1 stop

CLE11:56 pmCleveland Hopkins Intl

$487

American Airlines

Nov 26

CLE6:00 amCleveland Hopkins Intl

7h 15m

1 stop

SXM2:15 pmSimpson Bay Princess Juliana

Dec 5

SXM4:30 pmSimpson Bay Princess Juliana

18h 05m

2 stops

CLE9:35 amCleveland Hopkins Intl

$492

American Airlines

Dec 9

CLE5:16 amCleveland Hopkins Intl

10h 10m

2 stops

SXM4:26 pmSimpson Bay Princess Juliana

Dec 16

SXM3:27 pmSimpson Bay Princess Juliana

19h 09m

2 stops

CLE9:36 amCleveland Hopkins Intl

$497

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

Wed 12/9

6:55 pm-2:35 pm

2 stops18h 40m

Simpson Bay Princess Juliana

Wed 12/16

4:50 pm-6:19 pm

1 stop26h 29m

$442

ClevelandSimpson Bay

CLE Cleveland Hopkins Intl - SXM Simpson Bay Princess Juliana

CLESXM

Cleveland Hopkins Intl

Thu 12/3

6:55 pm-2:45 pm

2 stops42h 50m

Simpson Bay Princess Juliana

Mon 12/7

4:50 pm-6:19 pm

1 stop26h 29m

$442

ClevelandSimpson Bay

CLE Cleveland Hopkins Intl - SXM Simpson Bay Princess Juliana

CLESXM

Cleveland Hopkins Intl

Thu 11/26

6:00 am-3:11 pm

1 stop8h 11m

Simpson Bay Princess Juliana

Sat 12/5

3:30 pm-10:44 pm

1 stop8h 14m

$464

ClevelandSimpson Bay

CLE Cleveland Hopkins Intl - SXM Simpson Bay Princess Juliana

CLESXM

Cleveland Hopkins Intl

Thu 11/26

6:00 am-4:24 pm

1 stop9h 24m

Simpson Bay Princess Juliana

Sat 12/5

4:30 pm-11:56 pm

1 stop8h 26m

$487

ClevelandSimpson Bay

CLE Cleveland Hopkins Intl - SXM Simpson Bay Princess Juliana

CLESXM

Cleveland Hopkins Intl

Tue 12/1

8:09 pm-1:32 pm

1 stop16h 23m

Simpson Bay Princess Juliana

Tue 12/8

3:27 pm-11:23 pm

1 stop8h 56m

$487

Quickest round-trip

ClevelandSimpson Bay

CLE Cleveland Hopkins Intl - SXM Simpson Bay Princess Juliana

CLESXM

Cleveland Hopkins Intl

Tue 12/15

5:45 am-1:50 pm

1 stop7h 05m

Simpson Bay Princess Juliana

Tue 12/22

2:10 pm-10:22 pm

1 stop9h 12m

$487

ClevelandSimpson Bay

CLE Cleveland Hopkins Intl - SXM Simpson Bay Princess Juliana

CLESXM

Cleveland Hopkins Intl

Wed 12/9

6:00 am-2:40 pm

1 stop7h 40m

Simpson Bay Princess Juliana

Wed 12/16

4:05 pm-1:07 am

1 stop10h 02m

$487

ClevelandSimpson Bay

CLE Cleveland Hopkins Intl - SXM Simpson Bay Princess Juliana

CLESXM

Cleveland Hopkins Intl

Sat 1/23

7:43 pm-1:50 pm

1 stop17h 07m

Simpson Bay Princess Juliana

Sat 1/30

5:00 pm-9:47 am

1 stop17h 47m

$495

ClevelandSimpson Bay

CLE Cleveland Hopkins Intl - SXM Simpson Bay Princess Juliana

CLESXM

Cleveland Hopkins Intl

Mon 4/12

6:00 pm-12:10 pm

1 stop18h 10m

Simpson Bay Princess Juliana

Wed 4/14

1:35 pm-11:06 pm

1 stop9h 31m

$495

ClevelandSimpson Bay

CLE Cleveland Hopkins Intl - SXM Simpson Bay Princess Juliana

CLESXM

Cleveland Hopkins Intl

Wed 12/16

6:00 am-3:11 pm

1 stop8h 11m

Simpson Bay Princess Juliana

Wed 12/23

1:41 pm-9:29 pm

1 stop8h 48m

$510

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 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 $655 to $803.
The lowest price recently found on this route was $442.

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 October is also cheap. Prices for this month can be found on momondo for an average of $511.

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	$244
Fastest flight time	6h 33m
Direct flights	None

The best one-way flight to Simpson Bay from Cleveland in the past 72 hours is $244. The best round-trip flight deal from Cleveland to Simpson Bay found on momondo in the last 72 hours is $442.

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

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 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 4 as of November 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 United Airlines (15%), Delta (14%), and JetBlue (10%).

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 8,696 reviews	Search Delta flights
JetBlue	PriceFrom $276	Free Cancellation	Rating 7.1 3,065 reviews	Search JetBlue flights
American Airlines	PriceFrom $435	Free Cancellation	Rating 7.0 12,229 reviews	Search American Airlines flights
United Airlines	PriceFrom $447	Free Cancellation	Rating 7.3 10,460 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 $244

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 11/19. 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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JetBlue flights from Cleveland to Simpson Bay

Our best JetBlue deals on Cleveland to Simpson Bay flight tickets

American Airlines flights from Cleveland to Simpson Bay

Our best American Airlines 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 typical price of a round-trip flight between Cleveland and Simpson Bay?

What is the cheapest month to fly 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.

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

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Fly your favorite airline to Simpson Bay

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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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