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Westchester County

$105+ Cheap flights from Cleveland (CLE) to Westchester County

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 1/20. Fares are subject to change and may not be available on all flights or dates of travel.
CLE — HPN
Jan 31 — Feb 71
Sat 1/31
Sat 2/7
1 adult, Economy
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Cheap flight deals from Cleveland to Westchester County

Cheapest flights from Cleveland to Westchester County
Explore the most affordable flight options available from Cleveland to Westchester County. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 1, 2026.

This American Airlines deal was found by Cheapflights users on 12/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/318:00 amCLE - HPN
1 stop5h 05mAmerican Airlines
Fri 1/26:56 pmHPN - CLE
1 stop5h 29mAmerican Airlines
Deal found 12/29$487
This Kiwi.com deal was found by Cheapflights users on 12/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/319:30 pmCLE - HPN
2 stops15h 09mMultiple Airlines
Fri 1/212:10 pmHPN - CLE
1 stop10h 01mMultiple Airlines
Deal found 12/29$603
This American Airlines deal was found by Cheapflights users on 12/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/307:58 pmCLE - HPN
1 stop15h 31mAmerican Airlines
Fri 1/26:56 pmHPN - CLE
1 stop5h 29mAmerican Airlines
Deal found 12/29$712
This Kiwi.com deal was found by Cheapflights users on 12/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/309:30 pmCLE - HPN
2 stops37h 59mMultiple Airlines
Fri 1/212:10 pmHPN - CLE
1 stop10h 01mMultiple Airlines
Deal found 12/29$953
This Delta deal was found by Cheapflights users on 12/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/306:05 amCLE - HPN
1 stop5h 55mDelta
Fri 1/212:45 pmHPN - CLE
1 stop6h 01mDelta
Deal found 12/29$1,014
This Delta deal was found by Cheapflights users on 12/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/302:20 pmCLE - HPN
1 stop7h 49mDelta
Thu 1/16:03 amHPN - CLE
1 stop7h 32mDelta
Deal found 12/29$1,190

Find flight deals from Cleveland to Westchester County

Keep the following information in mind while searching for Cleveland to Westchester County flight deals. Data was last updated January 1, 2026.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$209
(American Airlines)

One-way from

$105
(Delta)

Popular in

November

Cheapest in

February

Average price

$189
Provider with most accurate pricing for Cleveland Hopkins Intl-New York (NYC) flight deals.
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Provider most trusted by Cheapflights users for Cleveland Hopkins Intl-New York (NYC) flights.
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From Cleveland Hopkins Intl to Westchester County
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One-way flight from Cleveland Hopkins Intl to Westchester County
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Highest demand for flights based on searches. 21% potential increase in price ($52 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($6 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Cleveland to Westchester County 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, Cheapflights users made 2,558,603 searches. Data last updated January 1, 2026.
Use the filters below to find and compare flights from Cleveland to Westchester County that are best for you.

Fly from

Cleveland

Fly to

Westchester County

Route

Depart

Return

Price

ClevelandWhite Plains

CLE - HPN

CLEHPN

Cleveland Hopkins Intl

Wed 1/28

10:20 am-3:49 pm

1 stop5h 29m

White Plains Westchester County

Sat 1/31

5:15 pm-12:36 am

1 stop7h 21m

$209

ClevelandWhite Plains

CLE - HPN

CLEHPN

Cleveland Hopkins Intl

Mon 1/26

10:30 am-2:39 pm

1 stop4h 09m

White Plains Westchester County

Mon 2/2

3:09 pm-7:17 pm

1 stop4h 08m

$209

ClevelandWhite Plains

CLE - HPN

CLEHPN

Cleveland Hopkins Intl

Mon 1/12

7:24 pm-11:28 am

2 stops16h 04m

White Plains Westchester County

Mon 1/19

12:08 pm-12:07 am

1 stop11h 59m

$219

ClevelandWhite Plains

CLE - HPN

CLEHPN

Cleveland Hopkins Intl

Sat 1/17

6:30 am-11:56 am

1 stop5h 26m

White Plains Westchester County

Tue 1/20

12:59 pm-7:26 pm

1 stop6h 27m

$227

ClevelandWhite Plains

CLE - HPN

CLEHPN

Cleveland Hopkins Intl

Mon 1/26

6:00 am-2:26 pm

1 stop8h 26m

White Plains Westchester County

Mon 2/2

12:38 pm-8:41 pm

2 stops8h 03m

$234

ClevelandWhite Plains

CLE - HPN

CLEHPN

Cleveland Hopkins Intl

Sat 1/17

4:54 pm-11:28 am

2 stops18h 34m

White Plains Westchester County

Mon 1/19

12:08 pm-12:07 am

1 stop11h 59m

$238

ClevelandWhite Plains

CLE - HPN

CLEHPN

Cleveland Hopkins Intl

Thu 1/15

6:00 am-12:06 pm

1 stop6h 06m

White Plains Westchester County

Tue 1/20

4:29 pm-10:41 pm

1 stop6h 12m

$244

ClevelandWhite Plains

CLE - HPN

CLEHPN

Cleveland Hopkins Intl

Fri 1/16

6:00 am-12:06 pm

1 stop6h 06m

White Plains Westchester County

Thu 1/22

10:29 am-6:27 pm

1 stop7h 58m

$244

ClevelandWhite Plains

CLE - HPN

CLEHPN

Cleveland Hopkins Intl

Fri 1/16

6:00 am-12:06 pm

1 stop6h 06m

White Plains Westchester County

Tue 1/20

6:00 am-1:22 pm

1 stop7h 22m

$244

ClevelandWhite Plains

CLE - HPN

CLEHPN

Cleveland Hopkins Intl

Wed 1/14

7:45 am-2:26 pm

1 stop6h 41m

White Plains Westchester County

Fri 1/23

3:10 pm-10:54 pm

1 stop7h 44m

$244

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/30

Showing 1-10 of 19 results
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Best time to book a flight from Cleveland to Westchester County

Have a flexible travel schedule? Discover the best time to fly to Westchester County 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 Westchester County

What is the cheapest month to book a flight from Cleveland to Westchester County?

Currently, March is the cheapest month in which you can book a flight from Cleveland to Westchester County (average of $134). Flying from Cleveland to Westchester County in November is currently the most expensive (average of $249). 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.

Reviews of airlines servicing Westchester County

Get insights into the airlines that provide service to Westchester County. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Westchester County. Reviews last updated January 1, 2026.
Peruse reviews from past customers who have flown with American Airlines from Cleveland to Westchester County to help guide your decision. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.2
Good
11,069 reviews

Food

6.4

Entertainment

6.9

Comfort

7.2

Overall

7.2

Crew

8.0

Boarding

7.5

Reviews

1 / 20
10.0
Excellent

Jeremy,Dec 2025

OKC - CLT

Was an okay flight. Had extra seat empty beside me so was able to stretch a bit
American Airlines
7.2
Good
11,069 reviews
American Airlines
7.2
Good
11,069 reviews

Food

6.4

Entertainment

6.9

Comfort

7.2

Overall

7.2

Crew

8.0

Boarding

7.5

Reviews

1 / 20
10.0
Excellent

Jeremy,Dec 2025

OKC - CLT

Was an okay flight. Had extra seat empty beside me so was able to stretch a bit

Related info for your journey

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

  • What airport do you fly from for flights from Cleveland to Westchester County?

    If you book a flight to Westchester County from Cleveland, you will be flying from Hopkins Intl, which is the city’s only airport. Cleveland Hopkins Intl (CLE) is located 10.1 mi from the center of Cleveland.

  • How long is the flight from Cleveland to Westchester County?

    There are many flights that can get you from Cleveland to Westchester County in 4h 09m. Fly via Delta or American Airlines to get the fastest option. Cleveland and Westchester County are separated by a distance of 423 mi. This flight may include one or multiple stops.

  • Can I find deals for flights from Cleveland to Westchester County that include hotel bookings?

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

  • How can I find direct flights from Cleveland to Westchester County?

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

  • Can I find deals for business class flights from Cleveland to Westchester County?

    Yes. Cheapflights offers flight deals from Cleveland to Westchester County 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 Westchester County?

    Currently, March is the cheapest month in which you can book a flight from Cleveland to Westchester County (average of $134). Flying from Cleveland to Westchester County in November is currently the most expensive (average of $249). 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.

See more FAQs

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Alternative routes for Cleveland to Westchester County

See prices for flight routes from nearby airports that may be better suited for you.
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Top airline flying from Cleveland to Westchester County

Discover the top airline that operate flights from Cleveland to Westchester County. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated January 1, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$199Average$257FlexibilityNo cancel feeOn-time71%

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