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Cheap flights from Cleveland to New York from $97

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 New York departing on 4/29. 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

Find the cheapest flights from Cleveland to New York

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
9:57 pm - 8:51 am
CLE
-
SWF
10h 54m
1 stop
Multiple Airlines Logo
9:41 am - 8:52 pm
SWF
-
CLE
11h 11m
1 stop
$257Multiple Airlines
Thu, May 28 - Mon, Jun 1
Multiple Airlines Logo
10:00 pm - 10:50 am
CLE
-
SWF
12h 50m
1 stop
Multiple Airlines Logo
9:38 am - 8:52 pm
SWF
-
CLE
11h 14m
1 stop
$262Multiple Airlines
Thu, Apr 30 - Thu, May 7
Multiple Airlines Logo
8:49 pm - 11:25 am
CLE
-
SWF
14h 36m
2 stops
Multiple Airlines Logo
12:05 pm - 5:27 pm
SWF
-
CLE
5h 22m
1 stop
$278Multiple Airlines
Tue, May 26 - Wed, Jun 3
Multiple Airlines Logo
9:57 pm - 8:58 am
CLE
-
SWF
11h 01m
1 stop
Multiple Airlines Logo
12:05 pm - 5:27 pm
SWF
-
CLE
5h 22m
1 stop
$280Multiple Airlines
Sat, May 23 - Sat, May 30
Multiple Airlines Logo
9:57 pm - 11:25 am
CLE
-
SWF
13h 28m
2 stops
Multiple Airlines Logo
9:38 am - 8:52 pm
SWF
-
CLE
11h 14m
1 stop
$288Multiple Airlines
Tue, May 5 - Thu, May 7
Multiple Airlines Logo
9:57 pm - 11:25 am
CLE
-
SWF
13h 28m
2 stops
Multiple Airlines Logo
9:38 am - 8:52 pm
SWF
-
CLE
11h 14m
1 stop
$293Multiple Airlines
Tue, May 5 - Thu, May 7
Multiple Airlines Logo
9:42 pm - 8:58 am
CLE
-
SWF
11h 16m
1 stop
Multiple Airlines Logo
12:05 pm - 5:03 pm
SWF
-
CLE
4h 58m
1 stop
$300Multiple Airlines
Wed, Jun 17 - Sat, Jun 20
Multiple Airlines Logo
7:38 pm - 10:55 am
CLE
-
SWF
15h 17m
1 stop
Multiple Airlines Logo
11:40 am - 11:59 pm
SWF
-
CLE
12h 19m
1 stop
$314Multiple Airlines
Wed, Apr 29 - Mon, May 4
Multiple Airlines Logo
3:46 pm - 9:38 am
CLE
-
SWF
17h 52m
2 stops
Multiple Airlines Logo
12:05 pm - 5:05 pm
SWF
-
CLE
5h 00m
1 stop
$322Multiple Airlines
Sat, Jul 18 - Wed, Jul 22
Multiple Airlines Logo
7:45 am - 5:03 pm
CLE
-
SWF
33h 18m
2 stops
Multiple Airlines Logo
9:38 am - 8:52 pm
SWF
-
CLE
11h 14m
1 stop
$325Multiple Airlines
Thu, May 21 - Thu, May 28

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Customize your flight search to find flights from Cleveland to New Windsor 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 April 25, 2026.
Use the filters below to find and compare flights from Cleveland to New Windsor that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ClevelandNew Windsor

CLE - SWF

CLESWF

Cleveland Hopkins Intl

Thu 5/28

9:57 pm-8:51 am

1 stop10h 54m

New Windsor Stewart

Mon 6/1

9:41 am-8:52 pm

1 stop11h 11m

$257

ClevelandNew Windsor

CLE - SWF

CLESWF

Cleveland Hopkins Intl

Thu 4/30

10:00 pm-10:50 am

1 stop12h 50m

New Windsor Stewart

Thu 5/7

9:38 am-8:52 pm

1 stop11h 14m

$262

ClevelandNew Windsor

CLE - SWF

CLESWF

Cleveland Hopkins Intl

Tue 5/26

8:49 pm-11:25 am

2 stops14h 36m

New Windsor Stewart

Wed 6/3

12:05 pm-5:27 pm

1 stop5h 22m

$278

ClevelandNew Windsor

CLE - SWF

CLESWF

Cleveland Hopkins Intl

Sat 5/23

9:57 pm-8:58 am

1 stop11h 01m

New Windsor Stewart

Sat 5/30

12:05 pm-5:27 pm

1 stop5h 22m

$280

ClevelandNew Windsor

CLE - SWF

CLESWF

Cleveland Hopkins Intl

Tue 5/5

9:57 pm-11:25 am

2 stops13h 28m

New Windsor Stewart

Thu 5/7

9:38 am-8:52 pm

1 stop11h 14m

$288

ClevelandNew Windsor

CLE - SWF

CLESWF

Cleveland Hopkins Intl

Tue 5/5

9:57 pm-11:25 am

2 stops13h 28m

New Windsor Stewart

Thu 5/7

9:38 am-8:52 pm

1 stop11h 14m

$293
Quickest round-trip

ClevelandNew Windsor

CLE - SWF

CLESWF

Cleveland Hopkins Intl

Wed 6/17

9:42 pm-8:58 am

1 stop11h 16m

New Windsor Stewart

Sat 6/20

12:05 pm-5:03 pm

1 stop4h 58m

$300

ClevelandNew Windsor

CLE - SWF

CLESWF

Cleveland Hopkins Intl

Wed 4/29

7:38 pm-10:55 am

1 stop15h 17m

New Windsor Stewart

Mon 5/4

11:40 am-11:59 pm

1 stop12h 19m

$314

ClevelandNew Windsor

CLE - SWF

CLESWF

Cleveland Hopkins Intl

Sat 7/18

3:46 pm-9:38 am

2 stops17h 52m

New Windsor Stewart

Wed 7/22

12:05 pm-5:05 pm

1 stop5h 00m

$322

ClevelandNew Windsor

CLE - SWF

CLESWF

Cleveland Hopkins Intl

Thu 5/21

7:45 am-5:03 pm

2 stops33h 18m

New Windsor Stewart

Thu 5/28

9:38 am-8:52 pm

1 stop11h 14m

$325

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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How to get the cheapest flight ticket from Cleveland to New Windsor

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 airlines fly to New Windsor?

Spirit Airlines, Delta and American Airlines are the top three most popular airlines that fly to New Windsor from Cleveland according to our data. Spirit Airlines is the first choice among our users, with 35% of people opting to fly with this airline when traveling to New Windsor. Keep in mind that there are 7 different airlines that fly to New Windsor on a routine basis, so you have a few additional options to choose from.

When to book flights from Cleveland to New Windsor

Are you open to changing your travel dates? Check out the ideal times to fly from Cleveland to New Windsor according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Cleveland to New Windsor (CLE to SWF) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Cleveland to New Windsor

Fastest flight time

10h 54m

Direct flights

None
The fastest flight from Cleveland to New Windsor takes 10h 54m
There are no direct flights from Cleveland to New Windsor. There are no popular flight routes from Cleveland to New Windsor.
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Frequently asked questions about flying from Cleveland to New Windsor

  • How far is Cleveland Hopkins Intl to New Windsor Stewart by plane?

    A flight from Cleveland Hopkins Intl to New Windsor Stewart will travel around 396.6 mi. Flights usually cover this in 10h 54m, depending on flying conditions and air traffic around both airports.

  • When did momondo last update prices for flights from Cleveland Hopkins Intl Airport to New Windsor Stewart Airport?

    Prices for flights from Cleveland Hopkins Intl Airport to New Windsor Stewart Airport are updated daily.

  • How old do you have to be to fly from Cleveland Hopkins Intl Airport to New Windsor Stewart 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 New Windsor Stewart Airport.

  • What documentation or ID do you need to fly to New Windsor Stewart Airport?

    The travel and health documents you'll need for your trip to New Windsor Stewart 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 New Windsor Stewart Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

Traveling to a place near New York?

Book flights to New York if you plan to visit one of these locations
Newburgh
Kingston
Woodstock
Saugerties

Why use momondo?

Why should I use momondo to find a flight deal from Cleveland to New Windsor?

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Cleveland to New Windsor. Millions of users trust and use momondo every year so you are in good hands.

Can I find flights from Cleveland to New Windsor with flexible booking policies on momondo?

Flights from Cleveland to New Windsor with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

How can momondo help me find flights from Cleveland to New Windsor?

momondo provides multiple filters to help you find the best flight to New Windsor from Cleveland. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Cleveland to New Windsor right now. Can momondo alert me if prices change?

Of course. momondo tracks the price of Cleveland to New Windsor flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

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