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Westchester County

$140+ Cheap flights from Chicago (CHI) 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 11/20. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — HPN
Nov 19 — Nov 261
1 adult
Tue 11/19
Tue 11/26
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Cheap flight deals from Chicago to Westchester County

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Westchester County (zzREU). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated November 14, 2024.

Find flight deals from Chicago to Westchester County

Cheapest flights from Chicago to Westchester County
Explore the most affordable flight options available from Chicago to Westchester County. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 14, 2024.

This American Airlines deal was found by Cheapflights users on 11/14. 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.
Thu 11/216:01 amORD - HPN
1 stop3h 58mAmerican Airlines
Sun 11/247:15 amHPN - ORD
Nonstop2h 39mAmerican Airlines
Deal found 11/14$279
This Delta deal was found by Cheapflights users on 11/14. 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.
Thu 11/217:10 amORD - HPN
1 stop7h 32mDelta
Sun 11/243:00 pmHPN - ORD
1 stop7h 15mDelta
Deal found 11/14$288
This Delta deal was found by Cheapflights users on 11/14. 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.
Thu 11/216:00 amMDW - HPN
1 stop7h 14mDelta
Sun 11/246:00 amHPN - MDW
1 stop6h 58mDelta
Deal found 11/14$288
This Mytrip deal was found by Cheapflights users on 11/14. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/84:19 pmORD - HPN
2 stops19h 11mMultiple Airlines
Wed 12/118:00 amHPN - ORD
2 stops17h 34mMultiple Airlines
Deal found 11/14$356

Find flights from Chicago to Westchester County within your budget

Customize your flight search to find flights from Chicago 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 2,752,363 searches. Data last updated November 14, 2024.

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Depart

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Price

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Tue 12/24

6:00 am-10:59 am

1 stop3h 59m

White Plains Westchester County

Sat 12/28

7:15 am-8:49 am

Nonstop2h 34m

$349

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Sun 12/8

4:19 pm-12:30 pm

2 stops19h 11m

White Plains Westchester County

Wed 12/11

8:00 am-12:34 am

2 stops17h 34m

$356

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Tue 12/3

10:15 am-4:30 pm

1 stop5h 15m

White Plains Westchester County

Tue 12/17

4:29 pm-11:58 pm

1 stop8h 29m

$383

ChicagoWhite Plains

MDW - HPN

MDWHPN

Chicago Midway

Thu 12/12

10:38 am-6:06 pm

1 stop6h 28m

White Plains Westchester County

Wed 12/18

12:30 pm-5:01 pm

1 stop5h 31m

$415

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Thu 11/21

6:00 am-12:04 pm

1 stop5h 04m

$144

ChicagoWhite Plains

MDW - HPN

MDWHPN

Chicago Midway

Thu 11/21

6:00 am-2:14 pm

1 stop7h 14m

$144

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Wed 1/1

6:00 am-2:40 pm

1 stop7h 40m

$210

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Mon 12/2

11:51 am-8:30 pm

3 stops31h 39m

$212

ChicagoWhite Plains

MDW - HPN

MDWHPN

Chicago Midway

Wed 1/1

11:48 am-11:50 am

3 stops23h 02m

$1,162

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/14

Best time to book a flight from Chicago to Westchester County

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

Travel insights for flights from Chicago to Westchester County

Get recent, data-driven insights about flights from Chicago to Westchester County including ideal travel times, pricing trends, and more.

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

Currently, January is the cheapest month in which you can book a flight from Chicago to Westchester County (average of $275). Flying from Chicago to Westchester County in June is currently the most expensive (average of $330). 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.

What is the cheapest time of day to fly from CHI to REU?

Find hourly flight availability from Chicago to Westchester County. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated November 14, 2024.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago to Westchester County as you normally would.

Weekly flight availability from Chicago to Westchester County

Explore weekly flight availability from Chicago to Westchester County. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated November 14, 2024.

The most flights from CHI to zzREU are scheduled on a Monday (6 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (5 on average).

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 November 14, 2024.
Read through reviews of airlines operating flights from Chicago to Westchester County, such as Delta and American Airlines. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
8,788 reviews

Crew

8.5

Food

7.3

Overall

8.0

Comfort

7.9

Boarding

8.2

Entertainment

7.9

Reviews

1 / 10

On time flights; courteous staff; efficient boarding system! Thank you!

Delta
8.0
Very good
8,788 reviews
Delta
8.0
Very good
8,788 reviews

Crew

8.5

Food

7.3

Overall

8.0

Comfort

7.9

Boarding

8.2

Entertainment

7.9

Reviews

1 / 10

On time flights; courteous staff; efficient boarding system! Thank you!

WestJet
7.3
Good
2,804 reviews
Delta
8.0
Very good
8,788 reviews

Crew

8.5

Food

7.3

Overall

8.0

Comfort

7.9

Boarding

8.2

Entertainment

7.9

Reviews

1 / 10

On time flights; courteous staff; efficient boarding system! Thank you!

American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
8,788 reviews

Crew

8.5

Food

7.3

Overall

8.0

Comfort

7.9

Boarding

8.2

Entertainment

7.9

Reviews

1 / 10

On time flights; courteous staff; efficient boarding system! Thank you!

Related info for your journey

Find useful and relevant information for your journey from Chicago 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 are the cheapest airlines to fly from Chicago to Westchester County one-way?

    One-way options have recently been found by users for as low as $144 on American Airlines. Other airlines that offer cheap prices include Delta from $144 and WestJet from $604 one-way.

  • What are the most reliable airlines from Chicago to Westchester County?

    No one likes to see their flight delayed. When booking a flight from Chicago to Westchester County consider choosing Qatar Airways (87%), American Airlines (86%) or Envoy Air (86%) as they are the most reliable in getting you off to your destination on time.

  • What are the cheapest flights from Chicago to Westchester County?

    While on average a flight from Chicago to Westchester County is generally $535, our data shows the cheapest flight currently is $207. When looking at the most popular route, (Chicago O'Hare Intl - White Plains Westchester County), you can expect to pay $279 for that flight.

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

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

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

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

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

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

    Currently, January is the cheapest month in which you can book a flight from Chicago to Westchester County (average of $275). Flying from Chicago to Westchester County in June is currently the most expensive (average of $330). 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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Alternative routes for Chicago to Westchester County

See prices for flight routes from nearby airports that may be better suited for you.
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Top 2 airlines flying from Chicago to Westchester County

Discover the top 2 airlines that operate flights from Chicago 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 2,752,363 searches. Data last updated November 14, 2024.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$159Average$373FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$234Average$439FlexibilityNo cancel feeOn-time71%
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