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Cheap flights from Cleveland to Simpson Bay from $192

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 1/31. 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.
Spirit Airlines Logo
10:54 am - 2:15 pmCLE-SXM
26h 21m1 stop
Spirit Airlines Logo
3:20 pm - 9:49 amSXM-CLE
19h 29m1 stop
$324Spirit Airlines
Find Deal
Sun, Dec 7 - Wed, Dec 10
Multiple Airlines Logo
3:40 pm - 2:15 pmCLE-SXM
21h 35m1 stop
Multiple Airlines Logo
3:20 pm - 9:49 amSXM-CLE
19h 29m1 stop
$335Multiple Airlines
Find Deal
Thu, Nov 27 - Sat, Dec 6
Multiple Airlines Logo
6:45 am - 2:15 pmCLE-SXM
30h 30m1 stop
Multiple Airlines Logo
3:20 pm - 1:45 pmSXM-CLE
23h 25m1 stop
$349Multiple Airlines
Find Deal
Sun, Dec 7 - Fri, Dec 12
Multiple Airlines Logo
6:45 am - 2:15 pmCLE-SXM
30h 30m1 stop
Multiple Airlines Logo
3:20 pm - 11:52 pmSXM-CLE
33h 32m2 stops
$370Multiple Airlines
Find Deal
Sun, Dec 7 - Fri, Dec 12
Air Canada Logo
6:10 pm - 4:00 pmCLE-SXM
20h 50m1 stop
Air Canada Logo
5:00 pm - 5:30 pmSXM-CLE
25h 30m1 stop
$463Air Canada
Find Deal
Tue, Jan 20 - Wed, Jan 28
Air Canada Logo
6:15 pm - 2:50 pmCLE-SXM
20h 35m1 stop
Air Canada Logo
4:00 pm - 5:30 pmSXM-CLE
25h 30m1 stop
$493Air Canada
Find Deal
Mon, Mar 30 - Fri, Apr 3
JetBlue Logo
9:00 am - 2:28 pmCLE-SXM
28h 28m2 stops
JetBlue Logo
3:43 pm - 8:40 pmSXM-CLE
29h 57m2 stops
$499JetBlue
Find Deal
Tue, Jan 20 - Wed, Jan 28
American Airlines Logo
6:57 pm - 12:50 pmCLE-SXM
16h 53m1 stop
American Airlines Logo
2:15 pm - 10:35 pmSXM-CLE
8h 20m1 stop
$537American Airlines
Find Deal
Sat, Mar 7 - Wed, Mar 11
American Airlines Logo
6:46 pm - 1:10 pmCLE-SXM
17h 24m2 stops
American Airlines Logo
3:07 pm - 8:42 amSXM-CLE
17h 35m2 stops
$542American Airlines
Find Deal
Sat, Mar 7 - Wed, Mar 11
Delta Logo
6:00 am - 2:55 pmCLE-SXM
7h 55m1 stop
Delta Logo
3:25 pm - 12:27 amSXM-CLE
10h 02m1 stop
$661Delta
Find Deal
Thu, Nov 27 - Sat, Dec 6

Air Canada flights from Cleveland to Simpson Bay

Our best Air Canada deals on Cleveland to Simpson Bay flight tickets
Air Canada
Jan 20
CLE6:10 pmCleveland Hopkins Intl
20h 50m
1 stop
SXM4:00 pmSimpson Bay Princess Juliana
Jan 28
SXM5:00 pmSimpson Bay Princess Juliana
25h 30m
1 stop
CLE5:30 pmCleveland Hopkins Intl
$463
Find similar
Air Canada
Mar 30
CLE6:15 pmCleveland Hopkins Intl
20h 35m
1 stop
SXM2:50 pmSimpson Bay Princess Juliana
Apr 3
SXM4:00 pmSimpson Bay Princess Juliana
25h 30m
1 stop
CLE5:30 pmCleveland Hopkins Intl
$493
Find similar
Air Canada
Mar 30
CLE6:15 pmCleveland Hopkins Intl
20h 35m
1 stop
SXM2:50 pmSimpson Bay Princess Juliana
Apr 3
SXM4:00 pmSimpson Bay Princess Juliana
25h 30m
1 stop
CLE5:30 pmCleveland Hopkins Intl
$496
Find similar

JetBlue flights from Cleveland to Simpson Bay

Our best JetBlue deals on Cleveland to Simpson Bay flight tickets
JetBlue
Jan 20
CLE9:00 amCleveland Hopkins Intl
28h 28m
2 stops
SXM2:28 pmSimpson Bay Princess Juliana
Jan 28
SXM3:43 pmSimpson Bay Princess Juliana
29h 57m
2 stops
CLE8:40 pmCleveland Hopkins Intl
$499
Find similar
JetBlue
Nov 9
CLE8:50 pmCleveland Hopkins Intl
16h 39m
2 stops
SXM2:29 pmSimpson Bay Princess Juliana
Nov 16
SXM5:44 pmSimpson Bay Princess Juliana
17h 56m
2 stops
CLE10:40 amCleveland Hopkins Intl
$918
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 November 4, 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 12/7

10:54 am-2:15 pm

1 stop26h 21m

Simpson Bay Princess Juliana

Wed 12/10

3:20 pm-9:49 am

1 stop19h 29m

$324

ClevelandSimpson Bay

CLE - SXM

CLESXM

Cleveland Hopkins Intl

Thu 11/27

3:40 pm-2:15 pm

1 stop21h 35m

Simpson Bay Princess Juliana

Sat 12/6

3:20 pm-9:49 am

1 stop19h 29m

$335

ClevelandSimpson Bay

CLE - SXM

CLESXM

Cleveland Hopkins Intl

Sun 12/7

6:45 am-2:15 pm

1 stop30h 30m

Simpson Bay Princess Juliana

Fri 12/12

3:20 pm-1:45 pm

1 stop23h 25m

$349

ClevelandSimpson Bay

CLE - SXM

CLESXM

Cleveland Hopkins Intl

Sun 12/7

6:45 am-2:15 pm

1 stop30h 30m

Simpson Bay Princess Juliana

Fri 12/12

3:20 pm-11:52 pm

2 stops33h 32m

$370

ClevelandSimpson Bay

CLE - SXM

CLESXM

Cleveland Hopkins Intl

Tue 1/20

6:10 pm-4:00 pm

1 stop20h 50m

Simpson Bay Princess Juliana

Wed 1/28

5:00 pm-5:30 pm

1 stop25h 30m

$463

ClevelandSimpson Bay

CLE - SXM

CLESXM

Cleveland Hopkins Intl

Mon 3/30

6:15 pm-2:50 pm

1 stop20h 35m

Simpson Bay Princess Juliana

Fri 4/3

4:00 pm-5:30 pm

1 stop25h 30m

$493

ClevelandSimpson Bay

CLE - SXM

CLESXM

Cleveland Hopkins Intl

Tue 1/20

9:00 am-2:28 pm

2 stops28h 28m

Simpson Bay Princess Juliana

Wed 1/28

3:43 pm-8:40 pm

2 stops29h 57m

$499

ClevelandSimpson Bay

CLE - SXM

CLESXM

Cleveland Hopkins Intl

Sat 3/7

6:57 pm-12:50 pm

1 stop16h 53m

Simpson Bay Princess Juliana

Wed 3/11

2:15 pm-10:35 pm

1 stop8h 20m

$537

ClevelandSimpson Bay

CLE - SXM

CLESXM

Cleveland Hopkins Intl

Sat 3/7

6:46 pm-1:10 pm

2 stops17h 24m

Simpson Bay Princess Juliana

Wed 3/11

3:07 pm-8:42 am

2 stops17h 35m

$542

ClevelandSimpson Bay

CLE - SXM

CLESXM

Cleveland Hopkins Intl

Thu 11/27

6:00 am-2:55 pm

1 stop7h 55m

Simpson Bay Princess Juliana

Sat 12/6

3:25 pm-12:27 am

1 stop10h 02m

$661

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 14 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, May 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 $567. If you aren’t able to travel to Simpson Bay during the month of May, then flying in September is also cheap. Prices for this month can be found on momondo for an average of $582.

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 $668 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 52m, 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
9,002 reviews
Search United Airlines flights
DeltaPriceFrom $460Free CancellationRating
7.9
8,003 reviews
Search Delta flights
American AirlinesPriceFrom $537Free CancellationRating
7.2
11,040 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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