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

United Airlines 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.

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.

What airlines fly to Simpson Bay?

American Airlines, Delta and JetBlue 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 4 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 connection time from Cleveland to Simpson Bay?

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

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

Atlanta (ATL) was the most common stop: 50% of momondo users choosing 1-stop flights on this route connected there.

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 June 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.

$198 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 $797 to $541. The lowest price recently found on this route was $479.

Discover deals from 900+ travel sites with momondo.

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.

6:25 am - 1:42 pm

CLE

SXM

7h 17m

1 stop

1:42 pm - 11:59 pm

SXM

CLE

10h 17m

1 stop

$479JetBlue

dom., ago. 30 - jue., sep. 3

6:01 am - 3:44 pm

CLE

SXM

9h 43m

1 stop

2:42 pm - 11:38 pm

SXM

CLE

8h 56m

1 stop

$493American Airlines

lun., ago. 3 - jue., ago. 13

6:25 am - 1:42 pm

CLE

SXM

7h 17m

1 stop

1:42 pm - 11:59 pm

SXM

CLE

10h 17m

1 stop

$496JetBlue

mié., ago. 19 - mié., ago. 26

8:47 pm - 3:44 pm

CLE

SXM

18h 57m

2 stops

2:42 pm - 11:38 pm

SXM

CLE

8h 56m

1 stop

$498American Airlines

lun., ago. 3 - jue., ago. 13

5:12 pm - 12:34 pm

CLE

SXM

19h 22m

1 stop

2:51 pm - 10:21 pm

SXM

CLE

7h 30m

1 stop

$501American Airlines

vie., jul. 3 - mar., jul. 7

6:15 am - 3:39 pm

CLE

SXM

9h 24m

1 stop

4:39 pm - 11:46 am

SXM

CLE

19h 07m

2 stops

$503American Airlines

dom., ago. 9 - dom., ago. 16

1:23 pm - 2:00 pm

CLE

SXM

23h 37m

1 stop

5:25 pm - 10:30 am

SXM

CLE

18h 05m

2 stops

$505American Airlines

jue., nov. 26 - sáb., dic. 5

5:29 pm - 2:00 pm

CLE

SXM

19h 31m

1 stop

3:20 pm - 11:55 pm

SXM

CLE

9h 35m

1 stop

$506American Airlines

sáb., nov. 14 - dom., nov. 22

6:15 am - 3:39 pm

CLE

SXM

9h 24m

1 stop

2:22 pm - 9:35 am

SXM

CLE

19h 13m

2 stops

$508American Airlines

mié., ago. 5 - dom., ago. 9

5:09 pm - 4:20 pm

CLE

SXM

22h 11m

1 stop

5:25 pm - 10:30 am

SXM

CLE

18h 05m

2 stops

$509American Airlines

jue., nov. 26 - sáb., dic. 5

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JetBlue flights from Cleveland to Simpson Bay

Our best JetBlue deals on Cleveland to Simpson Bay flight tickets

JetBlue

Aug 30

CLE6:25 amCleveland Hopkins Intl

7h 17m

1 stop

SXM1:42 pmSimpson Bay Princess Juliana

Sep 3

SXM1:42 pmSimpson Bay Princess Juliana

10h 17m

1 stop

CLE11:59 pmCleveland Hopkins Intl

$479

JetBlue

Aug 19

CLE6:25 amCleveland Hopkins Intl

7h 17m

1 stop

SXM1:42 pmSimpson Bay Princess Juliana

Aug 26

SXM1:42 pmSimpson Bay Princess Juliana

10h 17m

1 stop

CLE11:59 pmCleveland Hopkins Intl

$496

JetBlue

Aug 23

CLE6:25 amCleveland Hopkins Intl

7h 17m

1 stop

SXM1:42 pmSimpson Bay Princess Juliana

Aug 27

SXM1:42 pmSimpson Bay Princess Juliana

10h 17m

1 stop

CLE11:59 pmCleveland Hopkins Intl

$521

American Airlines flights from Cleveland to Simpson Bay

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

American Airlines

Aug 3

CLE6:01 amCleveland Hopkins Intl

9h 43m

1 stop

SXM3:44 pmSimpson Bay Princess Juliana

Aug 13

SXM2:42 pmSimpson Bay Princess Juliana

8h 56m

1 stop

CLE11:38 pmCleveland Hopkins Intl

$493

American Airlines

Aug 3

CLE8:47 pmCleveland Hopkins Intl

18h 57m

2 stops

SXM3:44 pmSimpson Bay Princess Juliana

Aug 13

SXM2:42 pmSimpson Bay Princess Juliana

8h 56m

1 stop

CLE11:38 pmCleveland Hopkins Intl

$498

American Airlines

Jul 3

CLE5:12 pmCleveland Hopkins Intl

19h 22m

1 stop

SXM12:34 pmSimpson Bay Princess Juliana

Jul 7

SXM2:51 pmSimpson Bay Princess Juliana

7h 30m

1 stop

CLE10:21 pmCleveland Hopkins Intl

$501

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Quickest round-trip

ClevelandSimpson Bay

CLE - SXM

CLESXM

Cleveland Hopkins Intl

dom. 8/30

6:25 am-1:42 pm

1 stop7h 17m

Simpson Bay Princess Juliana

jue. 9/3

1:42 pm-11:59 pm

1 stop10h 17m

$479

ClevelandSimpson Bay

CLE - SXM

CLESXM

Cleveland Hopkins Intl

lun. 8/3

6:01 am-3:44 pm

1 stop9h 43m

Simpson Bay Princess Juliana

jue. 8/13

2:42 pm-11:38 pm

1 stop8h 56m

$493

ClevelandSimpson Bay

CLE - SXM

CLESXM

Cleveland Hopkins Intl

mié. 8/19

6:25 am-1:42 pm

1 stop7h 17m

Simpson Bay Princess Juliana

mié. 8/26

1:42 pm-11:59 pm

1 stop10h 17m

$496

ClevelandSimpson Bay

CLE - SXM

CLESXM

Cleveland Hopkins Intl

lun. 8/3

8:47 pm-3:44 pm

2 stops18h 57m

Simpson Bay Princess Juliana

jue. 8/13

2:42 pm-11:38 pm

1 stop8h 56m

$498

ClevelandSimpson Bay

CLE - SXM

CLESXM

Cleveland Hopkins Intl

vie. 7/3

5:12 pm-12:34 pm

1 stop19h 22m

Simpson Bay Princess Juliana

mar. 7/7

2:51 pm-10:21 pm

1 stop7h 30m

$501

ClevelandSimpson Bay

CLE - SXM

CLESXM

Cleveland Hopkins Intl

dom. 8/9

6:15 am-3:39 pm

1 stop9h 24m

Simpson Bay Princess Juliana

dom. 8/16

4:39 pm-11:46 am

2 stops19h 07m

$503

ClevelandSimpson Bay

CLE - SXM

CLESXM

Cleveland Hopkins Intl

jue. 11/26

1:23 pm-2:00 pm

1 stop23h 37m

Simpson Bay Princess Juliana

sáb. 12/5

5:25 pm-10:30 am

2 stops18h 05m

$505

ClevelandSimpson Bay

CLE - SXM

CLESXM

Cleveland Hopkins Intl

sáb. 11/14

5:29 pm-2:00 pm

1 stop19h 31m

Simpson Bay Princess Juliana

dom. 11/22

3:20 pm-11:55 pm

1 stop9h 35m

$506

ClevelandSimpson Bay

CLE - SXM

CLESXM

Cleveland Hopkins Intl

mié. 8/5

6:15 am-3:39 pm

1 stop9h 24m

Simpson Bay Princess Juliana

dom. 8/9

2:22 pm-9:35 am

2 stops19h 13m

$508

ClevelandSimpson Bay

CLE - SXM

CLESXM

Cleveland Hopkins Intl

jue. 11/26

5:09 pm-4:20 pm

1 stop22h 11m

Simpson Bay Princess Juliana

sáb. 12/5

5:25 pm-10:30 am

2 stops18h 05m

$509

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 14 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, July 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 $498. If you aren’t able to travel to Simpson Bay during the month of July, then flying in April is also cheap. Prices for this month can be found on momondo for an average of $533.

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 $651 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 $547 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

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 3 as of June 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 (60% of total bookings). The next most popular airlines are Delta (31%) and United Airlines (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 $338	Free Cancellation	Rating 7.9 8,403 reviews	Search Delta flights
United Airlines	PriceFrom $447	Free Cancellation	Rating 7.4 9,805 reviews	Search United Airlines flights
American Airlines	PriceFrom $461	Free Cancellation	Rating 7.1 11,642 reviews	Search American Airlines flights

Philipsburg

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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 $198

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 6/26. 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?

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

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

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

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

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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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