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Westchester County

$119+ 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 1/23. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — HPN
Dec 29 — Jan 51
Sun 12/29
Sun 1/5
1 adult, Economy
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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 December 24, 2024.

Round-trip from

$330
(American Airlines)

One-way from

$119
(Mytrip)
From Chicago (CHI) to Westchester County
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One-way flight from Chicago (CHI) to Westchester County
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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 December 24, 2024.

This American Airlines deal was found by Cheapflights users on 12/24. 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.
Fri 12/276:35 pmORD - HPN
Nonstop2h 24mAmerican Airlines
Tue 12/317:15 amHPN - ORD
Nonstop2h 34mAmerican Airlines
Deal found 12/24$421
This Delta deal was found by Cheapflights users on 12/24. 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.
Fri 12/277:00 amORD - HPN
1 stop3h 50mDelta
Tue 12/3112:30 pmHPN - ORD
1 stop7h 22mDelta
Deal found 12/24$425
This Delta deal was found by Cheapflights users on 12/23. 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.
Mon 12/309:30 amMDW - HPN
1 stop6h 04mDelta
Wed 1/112:30 pmHPN - MDW
1 stop4h 40mDelta
Deal found 12/23$618
This United deal was found by Cheapflights users on 12/23. 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 United is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/246:25 pmORD - HPN
2 stops21h 27mMultiple Airlines
Sat 12/289:20 amHPN - ORD
2 stops23h 40mMultiple Airlines
Deal found 12/23$784

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 2,558,603 searches. Data last updated December 24, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Sat 1/25

6:32 pm-9:52 pm

Nonstop2h 20m

White Plains Westchester County

Sun 2/9

7:15 am-9:00 am

Nonstop2h 45m

$330

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Tue 1/14

5:55 pm-9:46 am

1 stop14h 51m

White Plains Westchester County

Sat 1/18

5:24 pm-9:15 pm

1 stop4h 51m

$331

ChicagoWhite Plains

MDW - HPN

MDWHPN

Chicago Midway

Tue 1/14

10:57 am-10:13 pm

1 stop10h 16m

White Plains Westchester County

Sat 1/18

4:29 pm-10:20 pm

1 stop6h 51m

$331

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Fri 5/9

4:57 pm-12:30 pm

2 stops18h 33m

White Plains Westchester County

Sun 5/11

12:10 pm-7:40 am

2 stops20h 30m

$365

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Thu 1/23

12:25 pm-12:30 pm

2 stops23h 05m

$119

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Tue 1/21

5:45 am-2:12 pm

1 stop7h 27m

$144

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Fri 1/24

8:25 pm-2:59 pm

1 stop17h 34m

$207

ChicagoWhite Plains

MDW - HPN

MDWHPN

Chicago Midway

Sat 2/1

9:34 am-4:44 pm

1 stop6h 10m

$403

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Wed 1/1

7:07 pm-8:03 pm

2 stops23h 56m

$1,003

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/24

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 $276). Flying from Chicago to Westchester County in March is currently the most expensive (average of $338). 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 December 24, 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 December 24, 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 (2 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 December 24, 2024.
Read through reviews of airlines operating flights from Chicago to Westchester County, such as American Airlines and Delta. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
9,555 reviews

Comfort

7.9

Food

7.2

Entertainment

7.1

Boarding

8.2

Crew

8.5

Overall

8.0

Reviews

1 / 10

Things were good, crew was good. It was just the flight itself was very rough. Lots of turbulence, probably one of the shakiest flights I've been on. Kids throwing up, kids crying everywhere because of it.

Alaska Airlines
8.0
Very good
9,555 reviews
Alaska Airlines
8.0
Very good
9,555 reviews

Comfort

7.9

Food

7.2

Entertainment

7.1

Boarding

8.2

Crew

8.5

Overall

8.0

Reviews

1 / 10

Things were good, crew was good. It was just the flight itself was very rough. Lots of turbulence, probably one of the shakiest flights I've been on. Kids throwing up, kids crying everywhere because of it.

Delta
8.0
Very good
8,580 reviews
Alaska Airlines
8.0
Very good
9,555 reviews

Comfort

7.9

Food

7.2

Entertainment

7.1

Boarding

8.2

Crew

8.5

Overall

8.0

Reviews

1 / 10

Things were good, crew was good. It was just the flight itself was very rough. Lots of turbulence, probably one of the shakiest flights I've been on. Kids throwing up, kids crying everywhere because of it.

American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
9,555 reviews

Comfort

7.9

Food

7.2

Entertainment

7.1

Boarding

8.2

Crew

8.5

Overall

8.0

Reviews

1 / 10

Things were good, crew was good. It was just the flight itself was very rough. Lots of turbulence, probably one of the shakiest flights I've been on. Kids throwing up, kids crying everywhere because of it.

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 Delta. Other airlines that offer cheap prices include American Airlines from $207 and Alaska Airlines from $1,003 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 American Airlines (82%), Envoy Air (82%) or Qatar Airways (70%) 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 $559, our data shows the cheapest flight currently is $203. When looking at the most popular route, (Chicago O'Hare Intl - White Plains Westchester County), you can expect to pay $332 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 $276). Flying from Chicago to Westchester County in March is currently the most expensive (average of $338). 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 2,558,603 searches. Data last updated December 24, 2024.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$159Average$356FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$240Average$438FlexibilityNo cancel feeOn-time71%
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