How far in advance should I book a flight from Cleveland to New Windsor?

To save up to 108% on this flight, we recommend booking at least 40 days prior to travel. The price may fluctuate and will likely increase closer to your departure date. Users on Cheapflights have found tickets from Cleveland to New Windsor from $160 1-2 weeks out and tickets from $215 for flights departing within the next 72 hours.

What is the cheapest month to fly from Cleveland to New Windsor?

Our data shows that February tends to be the cheapest month to fly to New Windsor from Cleveland. Users have commonly found prices around $180 for the month, but tickets can be as low as $38. Due to multiple factors, prepare for potentially higher prices in December.

What is the cheapest time of day to fly from CLE to SWF?

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Cleveland to New Windsor as you normally would.

Can I find deals for flights from Cleveland to Stewart that include hotel bookings?

Yes. In addition to deals on Cleveland to Stewart flights, Cheapflights offers vacation packages that include both flights and hotel.

How can I find direct flights from Cleveland to Stewart?

After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Cleveland to Stewart.

Can I find deals for business class flights from Cleveland to Stewart?

Yes. Cheapflights offers flight deals from Cleveland to Stewart by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

$111+ Flights from Cleveland to New Windsor

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1. Tell us where you want to go

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Cheap flight deals from Cleveland to Stewart

Round-trip from	$225 (Mytrip)
One-way from	$111 (Mytrip)
Popular in	December
Cheapest in	February
Average price	$179

From Cleveland Hopkins Intl to New Windsor Stewart

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One-way flight from Cleveland Hopkins Intl to New Windsor Stewart

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Highest demand for flights based on searches. 12% potential increase in price ($25 potential increase over avg. RT price).

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Cheapest flight prices on average. 2% potential price decrease ($5 potential savings vs. average RT price).

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Average for round-trip flights in July 2025

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Find flight deals from Cleveland to Stewart

Cheapest flights from Cleveland to Stewart
Explore the most affordable flight options available from Cleveland to Stewart. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 29, 2025.

Thu 10/27:51 pmCLE - SWF

1 stop15h 30mMultiple Airlines

Sun 10/55:45 pmSWF - CLE

1 stop15h 06mMultiple Airlines

Deal found 7/28

$225

Best flights from Cleveland to Stewart
Discover carefully curated flight deals from Cleveland to Stewart that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 29, 2025.

Thu 10/27:51 pmCLE - SWF

1 stop15h 30mMultiple Airlines

Sun 10/55:45 pmSWF - CLE

1 stop15h 06mMultiple Airlines

Deal found 7/28

$225

Last-minute flights from Cleveland to Stewart
Discover last-minute flight deals from Cleveland to Stewart. Data last updated July 29, 2025 and is based on user searches.

Thu 8/2111:11 amCLE - SWF

1 stop6h 49mMultiple Airlines

Sun 8/246:50 pmSWF - CLE

1 stop15h 26mMultiple Airlines

Deal found 7/29

$349

One-way flights from Cleveland to Stewart
Search for one-way flight options from Cleveland to Stewart. Find affordable one-way fares based on user searches. Data last updated July 29, 2025.

Sun 10/197:51 pmCLE - SWF

1 stop14h 20mMultiple Airlines

Deal found 7/27

$111

Fly from

Fly to

Route

Depart

Return

Price

ClevelandNew Windsor

CLE - SWF

CLESWF

Cleveland Hopkins Intl

Thu 10/2

7:51 pm-11:21 am

1 stop15h 30m

New Windsor Stewart

Sun 10/5

5:45 pm-8:51 am

1 stop15h 06m

$225

ClevelandNew Windsor

CLE - SWF

CLESWF

Cleveland Hopkins Intl

Sun 10/19

7:51 pm-10:11 am

1 stop14h 20m

$111

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/27

Best time to book a flight from Cleveland to Stewart

Have a flexible travel schedule? Discover the best time to fly to Stewart from Cleveland with our price prediction graph.

Estimated round-trip price

Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Cleveland to New Windsor

What is the cheapest month to book a flight from Cleveland to New Windsor?

Currently, October is the cheapest month in which you can book a flight from Cleveland to New Windsor (average of $109). Flying from Cleveland to New Windsor in August is currently the most expensive (average of $206). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

Related info for your journey

Can I find deals for flights from Cleveland to Stewart that include hotel bookings?
Yes. In addition to deals on Cleveland to Stewart flights, Cheapflights offers vacation packages that include both flights and hotel.
How can I find direct flights from Cleveland to Stewart?
After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Cleveland to Stewart.
Can I find deals for business class flights from Cleveland to Stewart?
Yes. Cheapflights offers flight deals from Cleveland to Stewart by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.
What is the cheapest month to book a flight from Cleveland to New Windsor?
Currently, October is the cheapest month in which you can book a flight from Cleveland to New Windsor (average of $109). Flying from Cleveland to New Windsor in August is currently the most expensive (average of $206). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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Complete your trip

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$111+ Cheap flights from Cleveland to New Windsor (CLE - SWF)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/19. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Cleveland to Stewart with Cheapflights

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

Cheap flight deals from Cleveland to Stewart

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Find flight deals from Cleveland to Stewart

Cheapest flights from Cleveland to StewartExplore the most affordable flight options available from Cleveland to Stewart. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 29, 2025.

Explore the most affordable flight options available from Cleveland to Stewart. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 29, 2025.

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Use the filters below to find and compare flights from Cleveland to New Windsor that are best for you.

Best time to book a flight from Cleveland to Stewart

Have a flexible travel schedule? Discover the best time to fly to Stewart from Cleveland with our price prediction graph.

Cheapflights Insights

Everything you need to know about your flight from Cleveland to New Windsor

What is the cheapest month to book a flight from Cleveland to New Windsor?

Related info for your journey

Find useful and relevant information for your journey from Cleveland to Stewart. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

Can I find deals for flights from Cleveland to Stewart that include hotel bookings?

How can I find direct flights from Cleveland to Stewart?

Can I find deals for business class flights from Cleveland to Stewart?

What is the cheapest month to book a flight from Cleveland to New Windsor?

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Cheapest flights from Cleveland to Stewart
Explore the most affordable flight options available from Cleveland to Stewart. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 29, 2025.