Cheap flights from Chicago (CHI) to Westchester County

CHI — HPN
Oct 2 — Oct 91

How far in advance should I book a flight from Chicago to Westchester County?

To save on the cost of your flight from Chicago to Westchester County, book at least 44 days before your planned departure. Booking around this time can save you about 73% on the cost of this flight compared to booking a flight leaving this week. We have found prices from $246 if you need a flight within two weeks. For flights within the next 72 hours, you can find tickets from as low as $302.

What is the cheapest month to fly from Chicago to Westchester County?

Our data shows that January tends to be the cheapest month to fly to Westchester County from Chicago. Users have commonly found prices around $216 for the month, but tickets can be as low as $110. Due to multiple factors, prepare for potentially higher prices in June.

When is the cheapest time to fly from Chicago to Westchester County (CHI - REU)?

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.

Cheap flights from Chicago to Westchester County in September, October 2022

The best prices found for CHI to Westchester County flights for September, October
Oct 25 - Oct 29
ORD

Chicago O'Hare Intl

HPN

White Plains Westchester County

Nonstop

2h 08m
HPN

White Plains Westchester County

ORD

Chicago O'Hare Intl

Nonstop

2h 34m
$207

American Airlines

Pick Dates

Deal found 9/26/22

Oct 19 - Oct 23
ORD

Chicago O'Hare Intl

HPN

White Plains Westchester County

Nonstop

2h 06m
HPN

White Plains Westchester County

ORD

Chicago O'Hare Intl

Nonstop

2h 35m
$208

United Airlines

Pick Dates

Deal found 9/25/22

Oct 19 - Oct 22
ORD

Chicago O'Hare Intl

HPN

White Plains Westchester County

Nonstop

2h 08m
HPN

White Plains Westchester County

ORD

Chicago O'Hare Intl

1 stop

5h 04m
$215

American Airlines

Pick Dates

Deal found 9/25/22

Chicago to Westchester County 2022 flight deals

Cheap flights to Westchester County from Chicago found for this year
Oct 25 - Oct 29
ORD

Chicago O'Hare Intl

HPN

White Plains Westchester County

Nonstop

2h 08m
HPN

White Plains Westchester County

ORD

Chicago O'Hare Intl

Nonstop

2h 34m
$207

American Airlines

Pick Dates

Deal found 9/26/22

Oct 19 - Oct 23
ORD

Chicago O'Hare Intl

HPN

White Plains Westchester County

Nonstop

2h 06m
HPN

White Plains Westchester County

ORD

Chicago O'Hare Intl

Nonstop

2h 35m
$208

United Airlines

Pick Dates

Deal found 9/25/22

Dec 7 - Dec 12
ORD

Chicago O'Hare Intl

HPN

White Plains Westchester County

1 stop

4h 54m
HPN

White Plains Westchester County

ORD

Chicago O'Hare Intl

Nonstop

2h 36m
$215

American Airlines

Pick Dates

Deal found 9/26/22

Cheap American Airlines flights from Chicago to Westchester County

Oct 25 - Oct 29
ORD

Chicago O'Hare Intl

HPN

White Plains Westchester County

Nonstop

2h 08m
HPN

White Plains Westchester County

ORD

Chicago O'Hare Intl

Nonstop

2h 34m
$207

American Airlines

Pick Dates

Deal found 9/26/22

Dec 7 - Dec 12
ORD

Chicago O'Hare Intl

HPN

White Plains Westchester County

1 stop

4h 54m
HPN

White Plains Westchester County

ORD

Chicago O'Hare Intl

Nonstop

2h 36m
$215

American Airlines

Pick Dates

Deal found 9/26/22

Oct 26 - Nov 2
ORD

Chicago O'Hare Intl

HPN

White Plains Westchester County

Nonstop

2h 12m
HPN

White Plains Westchester County

ORD

Chicago O'Hare Intl

1 stop

4h 53m
$217

American Airlines

Pick Dates

Deal found 9/26/22

Cheap United Airlines flights from Chicago to Westchester County

Oct 19 - Oct 23
ORD

Chicago O'Hare Intl

HPN

White Plains Westchester County

Nonstop

2h 06m
HPN

White Plains Westchester County

ORD

Chicago O'Hare Intl

Nonstop

2h 35m
$208

United Airlines

Pick Dates

Deal found 9/25/22

Dec 24 - Dec 29
ORD

Chicago O'Hare Intl

HPN

White Plains Westchester County

Nonstop

2h 12m
HPN

White Plains Westchester County

ORD

Chicago O'Hare Intl

Nonstop

2h 44m
$268

United Airlines

Pick Dates

Deal found 9/25/22

Oct 11 - Oct 16
ORD

Chicago O'Hare Intl

HPN

White Plains Westchester County

Nonstop

2h 15m
HPN

White Plains Westchester County

ORD

Chicago O'Hare Intl

Nonstop

2h 35m
$278

United Airlines

Pick Dates

Deal found 9/27/22

Non-stop flights to Westchester County from Chicago

Save time with Chicago to Westchester County direct flight deals
Oct 25 - Oct 29
ORD

Chicago O'Hare Intl

HPN

White Plains Westchester County

Nonstop

2h 08m
HPN

White Plains Westchester County

ORD

Chicago O'Hare Intl

Nonstop

2h 34m
$207

American Airlines

Pick Dates

Deal found 9/26/22

Oct 19 - Oct 23
ORD

Chicago O'Hare Intl

HPN

White Plains Westchester County

Nonstop

2h 06m
HPN

White Plains Westchester County

ORD

Chicago O'Hare Intl

Nonstop

2h 35m
$208

United Airlines

Pick Dates

Deal found 9/25/22

Oct 13 - Oct 17
ORD

Chicago O'Hare Intl

HPN

White Plains Westchester County

Nonstop

2h 08m
HPN

White Plains Westchester County

ORD

Chicago O'Hare Intl

Nonstop

2h 35m
$243

American Airlines

Pick Dates

Deal found 9/25/22

Last minute flights from Chicago to Westchester County

Late deals on return flights to Westchester County from Chicago, departing today and this week
Oct 2 - Nov 5
ORD

Chicago O'Hare Intl

HPN

White Plains Westchester County

Nonstop

2h 06m
HPN

White Plains Westchester County

ORD

Chicago O'Hare Intl

Nonstop

2h 42m
$293

United Airlines

Pick Dates

Deal found 9/25/22

Oct 6 - Oct 10
ORD

Chicago O'Hare Intl

HPN

White Plains Westchester County

Nonstop

2h 06m
HPN

White Plains Westchester County

ORD

Chicago O'Hare Intl

Nonstop

2h 35m
$328

United Airlines

Pick Dates

Deal found 9/25/22

Oct 6 - Oct 11
ORD

Chicago O'Hare Intl

HPN

White Plains Westchester County

1 stop

6h 43m
HPN

White Plains Westchester County

ORD

Chicago O'Hare Intl

Nonstop

2h 34m
$335

American Airlines

Pick Dates

Deal found 9/25/22

One-way flights to Westchester County from Chicago

The cheapest one-way flights from Chicago to Westchester County
Oct 19
MDW

Chicago Midway

HPN

White Plains Westchester County

2 stops

33h 56m
$125

Multiple Airlines

Pick Dates

Deal found 9/27/22

Oct 28
MDW

Chicago Midway

HPN

White Plains Westchester County

2 stops

33h 56m
$132

Multiple Airlines

Pick Dates

Deal found 9/26/22

Oct 8
ORD

Chicago O'Hare Intl

HPN

White Plains Westchester County

2 stops

14h 06m
$145

Multiple Airlines

Pick Dates

Deal found 9/26/22

Related info for your journey

Useful info, stats and facts about Chicago to Westchester County flights.

Which airlines flying from Chicago to Westchester County have flexible cancellations due to COVID-19?

Some of our airline partners flying from Chicago to Westchester County have new flexible policies in place due to COVID-19. American Airlines, United Airlines, and Juneyao Airlines are some of the carriers where you may find flexible cancellation policies. You can use our site to filter for airlines like American Airlines with this kind of flexibility.

Can I find flights from Chicago to Westchester County for under $300 on Cheapflights?

Yes, there are multiple flights from Chicago to Westchester County for under $300. The cheapest flight booked recently is on American Airlines for just $207, but on average you can expect to pay $242.

Are there nonstop flights from Chicago to Westchester County for under $300 on Cheapflights?

Cheapflights has at least 20 direct flights from Chicago to Westchester County under $300. A good price for a nonstop flight from Chicago to Westchester County is less than $325.

Are there last-minute flights available from Chicago to Westchester County for under $300?

There are currently 20+ open flights from Chicago to Westchester County within the next 7 days for less than $300.

What days are nonstop flights available from Chicago to Westchester County?

Nonstop flights can be found on the following days: Friday.

How many flights depart from Chicago to Westchester County on average per day?

On average 1 flight departs from Chicago to Westchester County per day.
Morning (6am - Noon) - 100% of flight departures

How long is the flight from Chicago to Westchester County?

For as low as $207, American Airlines can have you in Westchester County from Chicago in 2h 06m. Airlines will cover a distance of 740 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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 $219 on Delta. Other airlines that offer cheap prices include United Airlines from $221 and Frontier from $227 one-way.

What are the most popular airlines that fly from Chicago to Westchester County?

Consider American Airlines, Delta or Juneyao Airlines when booking your flight. These represent the most popular airlines when flying from Chicago to Westchester County.

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 United Airlines (82%), SkyWest Airlines (81%) or Alaska Airlines (79%) 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 $311, our data shows the cheapest flight currently is $167. When looking at the most popular route, (Chicago O'Hare Intl - White Plains Westchester County), you can expect to pay $208 for that flight.

Alternative routes for Chicago to Westchester County

See prices for flight routes from nearby airports that may be better suited for you.

Top 3 airlines flying from Chicago to Westchester County

The chart below displays the airlines Cheapflights users traveling from Chicago to Westchester County choose most often. Cheapest and average prices are based on aggregated data from the past 12 months.
AirlineCheapestAverageFlexibilityOn-timeCOVID-19 safety
Juneyao AirlinesCheapest$17Average$22FlexibilityNo cancel feeOn-time66%COVID-19 safety
Search Juneyao Airlines flights
American AirlinesCheapest$157Average$292FlexibilityNo cancel feeOn-time71%COVID-19 safety
Search American Airlines flights
United AirlinesCheapest$162Average$288FlexibilityNo cancel feeOn-time69%COVID-19 safety
Search United Airlines flights

Hourly flight availability from Chicago to Westchester County

See what time of day planes typically take off from Chicago to Westchester County
1%of flight departuresEarly morningMidnight to 6 am
41%of flight departuresMorning6 am to noon
23%of flight departuresAfternoonNoon to 6 pm
35%of flight departuresEvening6 pm to midnight
Midnight
6 AM
Noon
6 PM