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Cheap flights from Cleveland to Simpson Bay from $268

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 2/18. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Find the cheapest flights from Cleveland to Simpson Bay

Cheap round-trip flights

Multiple Airlines Logo
5:30 pm - 2:00 pmCLE-SXM
20h 30m1 stop
Multiple Airlines Logo
3:05 pm - 11:49 pmSXM-CLE
8h 44m1 stop
$435Multiple Airlines
Find Deal
Sun, Oct 12 - Sat, Oct 18
American Airlines Logo
6:06 am - 4:22 pmCLE-SXM
9h 16m1 stop
American Airlines Logo
2:51 pm - 11:49 pmSXM-CLE
9h 58m1 stop
$461American Airlines
Find Deal
Wed, Nov 12 - Wed, Nov 19
American Airlines Logo
6:00 am - 4:22 pmCLE-SXM
9h 22m2 stops
American Airlines Logo
2:51 pm - 9:36 pmSXM-CLE
7h 45m1 stop
$466American Airlines
Find Deal
Wed, Nov 12 - Wed, Nov 19
American Airlines Logo
1:23 pm - 2:00 pmCLE-SXM
23h 37m1 stop
American Airlines Logo
2:51 pm - 11:49 pmSXM-CLE
9h 58m1 stop
$469American Airlines
Find Deal
Sat, Nov 29 - Fri, Dec 5
Multiple Airlines Logo
12:15 pm - 3:10 pmCLE-SXM
25h 55m1 stop
Multiple Airlines Logo
4:28 pm - 11:33 amSXM-CLE
20h 05m2 stops
$470Multiple Airlines
Find Deal
Fri, Dec 5 - Mon, Dec 8
Multiple Airlines Logo
7:56 pm - 2:00 pmCLE-SXM
18h 04m1 stop
Multiple Airlines Logo
3:05 pm - 12:47 amSXM-CLE
33h 42m2 stops
$480Multiple Airlines
Find Deal
Sun, Oct 12 - Sat, Oct 18
Air Canada Logo
6:15 pm - 1:40 pmCLE-SXM
18h 25m2 stops
Air Canada Logo
4:00 pm - 5:36 pmSXM-CLE
25h 36m1 stop
$542Air Canada
Find Deal
Sat, Mar 7 - Wed, Mar 11
Air Canada Logo
6:15 pm - 1:40 pmCLE-SXM
18h 25m2 stops
Air Canada Logo
4:00 pm - 5:36 pmSXM-CLE
25h 36m1 stop
$550Air Canada
Find Deal
Sat, Mar 7 - Wed, Mar 11
Spirit Airlines Logo
5:43 pm - 2:00 pmCLE-SXM
20h 17m2 stops
Spirit Airlines Logo
3:05 pm - 4:48 pmSXM-CLE
25h 43m3 stops
$593Spirit Airlines
Find Deal
Sun, Oct 12 - Sat, Oct 18
Spirit Airlines Logo
5:43 pm - 2:00 pmCLE-SXM
20h 17m3 stops
Spirit Airlines Logo
3:05 pm - 4:48 pmSXM-CLE
25h 43m3 stops
$689Spirit Airlines
Find Deal
Sun, Oct 12 - Sat, Oct 18

American Airlines flights from Cleveland to Simpson Bay

Our best American Airlines deals on Cleveland to Simpson Bay flight tickets
American Airlines
Nov 12
CLE6:06 amCleveland Hopkins Intl
9h 16m
1 stop
SXM4:22 pmSimpson Bay Princess Juliana
Nov 19
SXM2:51 pmSimpson Bay Princess Juliana
9h 58m
1 stop
CLE11:49 pmCleveland Hopkins Intl
$461
Find similar
American Airlines
Nov 12
CLE6:00 amCleveland Hopkins Intl
9h 22m
2 stops
SXM4:22 pmSimpson Bay Princess Juliana
Nov 19
SXM2:51 pmSimpson Bay Princess Juliana
7h 45m
1 stop
CLE9:36 pmCleveland Hopkins Intl
$466
Find similar
American Airlines
Nov 29
CLE1:23 pmCleveland Hopkins Intl
23h 37m
1 stop
SXM2:00 pmSimpson Bay Princess Juliana
Dec 5
SXM2:51 pmSimpson Bay Princess Juliana
9h 58m
1 stop
CLE11:49 pmCleveland Hopkins Intl
$469
Find similar

Air Canada flights from Cleveland to Simpson Bay

Our best Air Canada deals on Cleveland to Simpson Bay flight tickets
Air Canada
Mar 7
CLE6:15 pmCleveland Hopkins Intl
18h 25m
2 stops
SXM1:40 pmSimpson Bay Princess Juliana
Mar 11
SXM4:00 pmSimpson Bay Princess Juliana
25h 36m
1 stop
CLE5:36 pmCleveland Hopkins Intl
$542
Find similar
Air Canada
Mar 7
CLE6:15 pmCleveland Hopkins Intl
18h 25m
2 stops
SXM1:40 pmSimpson Bay Princess Juliana
Mar 11
SXM4:00 pmSimpson Bay Princess Juliana
25h 36m
1 stop
CLE5:36 pmCleveland Hopkins Intl
$550
Find similar
Air Canada
Dec 5
CLE6:15 pmCleveland Hopkins Intl
19h 25m
2 stops
SXM2:40 pmSimpson Bay Princess Juliana
Dec 8
SXM5:00 pmSimpson Bay Princess Juliana
26h 16m
3 stops
CLE6:16 pmCleveland Hopkins Intl
$751
Find similar

momondo 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, momondo users made 832,500 searches. Data last updated September 18, 2025.
Use the filters below to find and compare flights from Cleveland to Simpson Bay that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ClevelandSimpson Bay

CLE - SXM

CLESXM

Cleveland Hopkins Intl

Sun 10/12

5:30 pm-2:00 pm

1 stop20h 30m

Simpson Bay Princess Juliana

Sat 10/18

3:05 pm-11:49 pm

1 stop8h 44m

$435

ClevelandSimpson Bay

CLE - SXM

CLESXM

Cleveland Hopkins Intl

Wed 11/12

6:06 am-4:22 pm

1 stop9h 16m

Simpson Bay Princess Juliana

Wed 11/19

2:51 pm-11:49 pm

1 stop9h 58m

$461

ClevelandSimpson Bay

CLE - SXM

CLESXM

Cleveland Hopkins Intl

Wed 11/12

6:00 am-4:22 pm

2 stops9h 22m

Simpson Bay Princess Juliana

Wed 11/19

2:51 pm-9:36 pm

1 stop7h 45m

$466

ClevelandSimpson Bay

CLE - SXM

CLESXM

Cleveland Hopkins Intl

Sat 11/29

1:23 pm-2:00 pm

1 stop23h 37m

Simpson Bay Princess Juliana

Fri 12/5

2:51 pm-11:49 pm

1 stop9h 58m

$469

ClevelandSimpson Bay

CLE - SXM

CLESXM

Cleveland Hopkins Intl

Fri 12/5

12:15 pm-3:10 pm

1 stop25h 55m

Simpson Bay Princess Juliana

Mon 12/8

4:28 pm-11:33 am

2 stops20h 05m

$470

ClevelandSimpson Bay

CLE - SXM

CLESXM

Cleveland Hopkins Intl

Sun 10/12

7:56 pm-2:00 pm

1 stop18h 04m

Simpson Bay Princess Juliana

Sat 10/18

3:05 pm-12:47 am

2 stops33h 42m

$480

ClevelandSimpson Bay

CLE - SXM

CLESXM

Cleveland Hopkins Intl

Sat 3/7

6:15 pm-1:40 pm

2 stops18h 25m

Simpson Bay Princess Juliana

Wed 3/11

4:00 pm-5:36 pm

1 stop25h 36m

$542

ClevelandSimpson Bay

CLE - SXM

CLESXM

Cleveland Hopkins Intl

Sat 3/7

6:15 pm-1:40 pm

2 stops18h 25m

Simpson Bay Princess Juliana

Wed 3/11

4:00 pm-5:36 pm

1 stop25h 36m

$550

ClevelandSimpson Bay

CLE - SXM

CLESXM

Cleveland Hopkins Intl

Sun 10/12

5:43 pm-2:00 pm

2 stops20h 17m

Simpson Bay Princess Juliana

Sat 10/18

3:05 pm-4:48 pm

3 stops25h 43m

$593

ClevelandSimpson Bay

CLE - SXM

CLESXM

Cleveland Hopkins Intl

Sun 10/12

5:43 pm-2:00 pm

3 stops20h 17m

Simpson Bay Princess Juliana

Sat 10/18

3:05 pm-4:48 pm

3 stops25h 43m

$689

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 13 resultsSorted by cheapest first
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See travel insights to Simpson Bay from

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

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, November 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 $511. If you aren’t able to travel to Simpson Bay during the month of November, then flying in May is also cheap. Prices for this month can be found on momondo for an average of $568.

What is the cheapest day to depart on your flight to Simpson Bay?

Our data shows that Monday is the least expensive day to fly to Simpson Bay. Tickets to fly out on this day can be as low as $460. Flights from Cleveland to Simpson Bay on a Friday will generally be more expensive and average around $685. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

What is the cheapest time of day to depart on your flight to Simpson Bay?

According to our data, the cheapest time of day to fly to Simpson Bay is in the afternoon. momondo users have found flights departing from Cleveland to Simpson Bay in the afternoon for as low as $469. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. In contrast, the most expensive time of day to depart to Simpson Bay is in the morning when prices are around $590.

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 $639 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 $506 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

Direct flights

None
There are no direct flights from Cleveland to Simpson Bay. There are no popular flight routes from Cleveland to Simpson Bay.
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  • 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 10m, 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?

  • 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?

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
United AirlinesPriceFrom $455Free CancellationRating
7.4
8,925 reviews
Search United Airlines flights
DeltaPriceFrom $460Free CancellationRating
7.9
7,961 reviews
Search Delta flights
American AirlinesPriceFrom $505Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights

Traveling to a place near Simpson Bay?

Book flights to Simpson Bay if you plan to visit one of these locations
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.

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