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Cheap flights from Cleveland to Simpson Bay from $281

This is the cheapest round-trip flight price found by a momondo user in the last 72 hours by searching for a flight from Cleveland to Simpson Bay departing on 1/2. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Find the cheapest flights from Cleveland to Simpson Bay

Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
6:30 am - 1:30 pm
CLE
-
SXM
30h 00m1 stop
Frontier Logo
4:11 pm - 5:13 pm
SXM
-
CLE
26h 02m1 stop
$281Frontier
Fri, Jan 2 - Sat, Jan 10
Multiple Airlines Logo
6:30 am - 2:10 pm
CLE
-
SXM
30h 40m1 stop
Multiple Airlines Logo
3:15 pm - 10:44 pm
SXM
-
CLE
8h 29m1 stop
$283Multiple Airlines
Sun, Jan 18 - Fri, Jan 23
Multiple Airlines Logo
3:59 pm - 2:10 pm
CLE
-
SXM
21h 11m1 stop
Multiple Airlines Logo
3:15 pm - 7:43 pm
SXM
-
CLE
29h 28m1 stop
$288Multiple Airlines
Wed, Feb 4 - Mon, Feb 9
Multiple Airlines Logo
3:45 pm - 2:10 pm
CLE
-
SXM
21h 25m1 stop
Multiple Airlines Logo
3:15 pm - 11:11 pm
SXM
-
CLE
32h 56m2 stops
$301Multiple Airlines
Sun, Jan 18 - Fri, Jan 23
Multiple Airlines Logo
7:01 pm - 2:10 pm
CLE
-
SXM
18h 09m1 stop
Multiple Airlines Logo
3:15 pm - 7:34 am
SXM
-
CLE
17h 19m2 stops
$304Multiple Airlines
Wed, Feb 4 - Mon, Feb 9
Multiple Airlines Logo
8:46 pm - 2:10 pm
CLE
-
SXM
16h 24m2 stops
Multiple Airlines Logo
3:15 pm - 7:43 pm
SXM
-
CLE
29h 28m1 stop
$318Multiple Airlines
Thu, Feb 19 - Mon, Feb 23
Multiple Airlines Logo
9:30 am - 2:28 pm
CLE
-
SXM
27h 58m2 stops
Multiple Airlines Logo
3:10 pm - 11:11 pm
SXM
-
CLE
9h 01m1 stop
$347Multiple Airlines
Sat, Jan 24 - Sat, Jan 31
Multiple Airlines Logo
7:10 pm - 2:15 pm
CLE
-
SXM
18h 05m1 stop
Multiple Airlines Logo
3:20 pm - 11:59 pm
SXM
-
CLE
9h 39m1 stop
$351Multiple Airlines
Sat, Feb 21 - Sat, Feb 28
Multiple Airlines Logo
7:30 am - 2:10 pm
CLE
-
SXM
29h 40m1 stop
Multiple Airlines Logo
3:15 pm - 7:43 pm
SXM
-
CLE
29h 28m1 stop
$357Multiple Airlines
Thu, Feb 19 - Mon, Feb 23
Multiple Airlines Logo
6:16 pm - 2:10 pm
CLE
-
SXM
18h 54m1 stop
Multiple Airlines Logo
3:15 pm - 11:59 pm
SXM
-
CLE
9h 44m1 stop
$376Multiple Airlines
Sat, Feb 21 - Sat, Feb 28

Air Canada flights from Cleveland to Simpson Bay

Our best Air Canada deals on Cleveland to Simpson Bay flight tickets
Air Canada
Mar 28
CLE6:10 pmCleveland Hopkins Intl
19h 25m
2 stops
SXM1:35 pmSimpson Bay Princess Juliana
Apr 4
SXM4:00 pmSimpson Bay Princess Juliana
25h 30m
1 stop
CLE5:30 pmCleveland Hopkins Intl
$450
Find similar
Air Canada
Mar 28
CLE6:10 pmCleveland Hopkins Intl
19h 25m
2 stops
SXM1:35 pmSimpson Bay Princess Juliana
Apr 4
SXM2:40 pmSimpson Bay Princess Juliana
26h 50m
2 stops
CLE5:30 pmCleveland Hopkins Intl
$454
Find similar
Air Canada
Feb 2
CLE6:10 pmCleveland Hopkins Intl
20h 50m
1 stop
SXM4:00 pmSimpson Bay Princess Juliana
Feb 5
SXM3:40 pmSimpson Bay Princess Juliana
26h 50m
2 stops
CLE5:30 pmCleveland Hopkins Intl
$478
Find similar

American Airlines flights from Cleveland to Simpson Bay

Our best American Airlines deals on Cleveland to Simpson Bay flight tickets
American Airlines
Mar 7
CLE6:11 pmCleveland Hopkins Intl
16h 18m
1 stop
SXM11:29 amSimpson Bay Princess Juliana
Mar 11
SXM4:01 pmSimpson Bay Princess Juliana
18h 28m
1 stop
CLE10:29 amCleveland Hopkins Intl
$461
Find similar
American Airlines
Mar 7
CLE6:56 pmCleveland Hopkins Intl
17h 25m
2 stops
SXM1:21 pmSimpson Bay Princess Juliana
Mar 11
SXM12:29 pmSimpson Bay Princess Juliana
12h 05m
2 stops
CLE12:34 amCleveland Hopkins Intl
$466
Find similar
American Airlines
Feb 21
CLE3:40 pmCleveland Hopkins Intl
19h 58m
2 stops
SXM12:38 pmSimpson Bay Princess Juliana
Feb 28
SXM5:28 pmSimpson Bay Princess Juliana
19h 22m
2 stops
CLE11:50 amCleveland Hopkins Intl
$496
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 December 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

Fri 1/2

6:30 am-1:30 pm

1 stop30h 00m

Simpson Bay Princess Juliana

Sat 1/10

4:11 pm-5:13 pm

1 stop26h 02m

$281

ClevelandSimpson Bay

CLE - SXM

CLESXM

Cleveland Hopkins Intl

Sun 1/18

6:30 am-2:10 pm

1 stop30h 40m

Simpson Bay Princess Juliana

Fri 1/23

3:15 pm-10:44 pm

1 stop8h 29m

$283

ClevelandSimpson Bay

CLE - SXM

CLESXM

Cleveland Hopkins Intl

Wed 2/4

3:59 pm-2:10 pm

1 stop21h 11m

Simpson Bay Princess Juliana

Mon 2/9

3:15 pm-7:43 pm

1 stop29h 28m

$288

ClevelandSimpson Bay

CLE - SXM

CLESXM

Cleveland Hopkins Intl

Sun 1/18

3:45 pm-2:10 pm

1 stop21h 25m

Simpson Bay Princess Juliana

Fri 1/23

3:15 pm-11:11 pm

2 stops32h 56m

$301

ClevelandSimpson Bay

CLE - SXM

CLESXM

Cleveland Hopkins Intl

Wed 2/4

7:01 pm-2:10 pm

1 stop18h 09m

Simpson Bay Princess Juliana

Mon 2/9

3:15 pm-7:34 am

2 stops17h 19m

$304

ClevelandSimpson Bay

CLE - SXM

CLESXM

Cleveland Hopkins Intl

Thu 2/19

8:46 pm-2:10 pm

2 stops16h 24m

Simpson Bay Princess Juliana

Mon 2/23

3:15 pm-7:43 pm

1 stop29h 28m

$318

ClevelandSimpson Bay

CLE - SXM

CLESXM

Cleveland Hopkins Intl

Sat 1/24

9:30 am-2:28 pm

2 stops27h 58m

Simpson Bay Princess Juliana

Sat 1/31

3:10 pm-11:11 pm

1 stop9h 01m

$347

ClevelandSimpson Bay

CLE - SXM

CLESXM

Cleveland Hopkins Intl

Sat 2/21

7:10 pm-2:15 pm

1 stop18h 05m

Simpson Bay Princess Juliana

Sat 2/28

3:20 pm-11:59 pm

1 stop9h 39m

$351

ClevelandSimpson Bay

CLE - SXM

CLESXM

Cleveland Hopkins Intl

Thu 2/19

7:30 am-2:10 pm

1 stop29h 40m

Simpson Bay Princess Juliana

Mon 2/23

3:15 pm-7:43 pm

1 stop29h 28m

$357

ClevelandSimpson Bay

CLE - SXM

CLESXM

Cleveland Hopkins Intl

Sat 2/21

6:16 pm-2:10 pm

1 stop18h 54m

Simpson Bay Princess Juliana

Sat 2/28

3:15 pm-11:59 pm

1 stop9h 44m

$376

Flights are sorted by cheapest round-trip flights first.

Sorted by cheapest first

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, September 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 $582. If you aren’t able to travel to Simpson Bay during the month of September, then flying in May is also cheap. Prices for this month can be found on momondo for an average of $587.

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 $673 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 $528 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

7h 12m

Direct flights

None
The fastest flight from Cleveland to Simpson Bay takes 7h 12m
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 7h 12m, 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
9,091 reviews
Search United Airlines flights
DeltaPriceFrom $481Free CancellationRating
7.9
8,005 reviews
Search Delta flights
American AirlinesPriceFrom $528Free CancellationRating
7.2
11,054 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.

An easier way to manage your Simpson Bay trip

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