Cheap flights from Westchester County to Chicago (CHI)

HPN — CHI
Aug 9 — Aug 161

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

Users have found that booking a flight from Westchester County to Chicago at least 26 days early can save you up to 21% on average compared to booking a flight this week. If booking 26 days before your flight isn’t an option for you, users have found flights from Westchester County to Chicago for as little as $256 when booking for a departure date within the next two weeks. You can also check prices now. Some users have found airline tickets as low as $300 for flights departing within the next 3 days.

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

Our data shows that January tends to be the cheapest month to fly to Chicago from Westchester County. Users have commonly found prices around $235 for the month, but tickets can be as low as $117. Due to multiple factors, prepare for potentially higher prices in August.

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

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

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

The best prices found for Westchester County to CHI flights for August, September
Sep 3 - Sep 4
HPN

White Plains Westchester County

ORD

Chicago O'Hare Intl

Nonstop

2h 45m
ORD

Chicago O'Hare Intl

HPN

White Plains Westchester County

Nonstop

2h 08m
$196

American Airlines

Pick Dates

Deal found 8/2/22

Sep 1 - Sep 4
HPN

White Plains Westchester County

ORD

Chicago O'Hare Intl

Nonstop

2h 37m
ORD

Chicago O'Hare Intl

HPN

White Plains Westchester County

Nonstop

2h 11m
$202

United Airlines

Pick Dates

Deal found 8/2/22

Sep 3 - Sep 4
HPN

White Plains Westchester County

ORD

Chicago O'Hare Intl

Nonstop

2h 45m
ORD

Chicago O'Hare Intl

HPN

White Plains Westchester County

1 stop

4h 43m
$203

American Airlines

Pick Dates

Deal found 8/3/22

Westchester County to Chicago 2022 flight deals

Cheap flights to Chicago from Westchester County found for this year
Sep 3 - Sep 4
HPN

White Plains Westchester County

ORD

Chicago O'Hare Intl

Nonstop

2h 45m
ORD

Chicago O'Hare Intl

HPN

White Plains Westchester County

Nonstop

2h 08m
$196

American Airlines

Pick Dates

Deal found 8/2/22

Sep 1 - Sep 4
HPN

White Plains Westchester County

ORD

Chicago O'Hare Intl

Nonstop

2h 37m
ORD

Chicago O'Hare Intl

HPN

White Plains Westchester County

Nonstop

2h 11m
$202

United Airlines

Pick Dates

Deal found 8/2/22

Sep 3 - Sep 4
HPN

White Plains Westchester County

ORD

Chicago O'Hare Intl

Nonstop

2h 45m
ORD

Chicago O'Hare Intl

HPN

White Plains Westchester County

1 stop

4h 43m
$203

American Airlines

Pick Dates

Deal found 8/3/22

Cheap United Airlines flights from Westchester County to Chicago

Sep 1 - Sep 4
HPN

White Plains Westchester County

ORD

Chicago O'Hare Intl

Nonstop

2h 37m
ORD

Chicago O'Hare Intl

HPN

White Plains Westchester County

Nonstop

2h 11m
$202

United Airlines

Pick Dates

Deal found 8/2/22

Sep 1 - Sep 7
HPN

White Plains Westchester County

ORD

Chicago O'Hare Intl

Nonstop

2h 37m
ORD

Chicago O'Hare Intl

HPN

White Plains Westchester County

Nonstop

2h 15m
$208

United Airlines

Pick Dates

Deal found 8/3/22

Sep 9 - Sep 11
HPN

White Plains Westchester County

ORD

Chicago O'Hare Intl

Nonstop

2h 35m
ORD

Chicago O'Hare Intl

HPN

White Plains Westchester County

Nonstop

2h 06m
$229

United Airlines

Pick Dates

Deal found 8/2/22

Cheap Delta flights from Westchester County to Chicago

Sep 1 - Sep 6
HPN

White Plains Westchester County

ORD

Chicago O'Hare Intl

1 stop

4h 46m
ORD

Chicago O'Hare Intl

HPN

White Plains Westchester County

1 stop

3h 42m
$226

Delta

Pick Dates

Deal found 8/3/22

Sep 3 - Sep 4
HPN

White Plains Westchester County

MDW

Chicago Midway

1 stop

3h 38m
MDW

Chicago Midway

HPN

White Plains Westchester County

1 stop

5h 03m
$236

Delta

Pick Dates

Deal found 8/3/22

Oct 28 - Oct 31
HPN

White Plains Westchester County

ORD

Chicago O'Hare Intl

1 stop

4h 24m
ORD

Chicago O'Hare Intl

HPN

White Plains Westchester County

1 stop

4h 26m
$242

Delta

Pick Dates

Deal found 8/1/22

Non-stop flights to Chicago from Westchester County

Save time with Westchester County to Chicago direct flight deals
Sep 3 - Sep 4
HPN

White Plains Westchester County

ORD

Chicago O'Hare Intl

Nonstop

2h 45m
ORD

Chicago O'Hare Intl

HPN

White Plains Westchester County

Nonstop

2h 08m
$196

American Airlines

Pick Dates

Deal found 8/2/22

Sep 1 - Sep 4
HPN

White Plains Westchester County

ORD

Chicago O'Hare Intl

Nonstop

2h 37m
ORD

Chicago O'Hare Intl

HPN

White Plains Westchester County

Nonstop

2h 11m
$202

United Airlines

Pick Dates

Deal found 8/2/22

Sep 1 - Sep 7
HPN

White Plains Westchester County

ORD

Chicago O'Hare Intl

Nonstop

2h 37m
ORD

Chicago O'Hare Intl

HPN

White Plains Westchester County

Nonstop

2h 15m
$208

United Airlines

Pick Dates

Deal found 8/3/22

Last minute flights from Westchester County to Chicago

Late deals on return flights to Chicago from Westchester County, departing today and this week
Aug 11 - Sep 3
HPN

White Plains Westchester County

ORD

Chicago O'Hare Intl

Nonstop

2h 37m
ORD

Chicago O'Hare Intl

HPN

White Plains Westchester County

Nonstop

2h 20m
$287

United Airlines

Pick Dates

Deal found 8/3/22

Aug 12 - Aug 31
HPN

White Plains Westchester County

ORD

Chicago O'Hare Intl

Nonstop

2h 37m
ORD

Chicago O'Hare Intl

HPN

White Plains Westchester County

Nonstop

2h 11m
$293

United Airlines

Pick Dates

Deal found 8/3/22

Aug 12 - Aug 31
HPN

White Plains Westchester County

ORD

Chicago O'Hare Intl

1 stop

4h 46m
ORD

Chicago O'Hare Intl

HPN

White Plains Westchester County

Nonstop

2h 08m
$300

American Airlines

Pick Dates

Deal found 8/3/22

One-way flights to Chicago from Westchester County

The cheapest one-way flights from Westchester County to Chicago
Sep 4
HPN

White Plains Westchester County

ORD

Chicago O'Hare Intl

Nonstop

2h 37m
$98

United Airlines

Pick Dates

Deal found 8/3/22

Sep 4
HPN

White Plains Westchester County

ORD

Chicago O'Hare Intl

1 stop

4h 43m
$106

American Airlines

Pick Dates

Deal found 8/1/22

Sep 4
HPN

White Plains Westchester County

MDW

Chicago Midway

1 stop

3h 38m
$107

Delta

Pick Dates

Deal found 8/1/22

Related info for your journey

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

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

American Airlines, United Airlines, and Delta are some of the carriers that may have flexible cancellation policies. You can use our site to filter for other airlines that may also have this kind of flexibility.

Can I find flights from Westchester County to Chicago for under $200 on Cheapflights?

Yes, there are multiple flights from Westchester County to Chicago for under $200. The cheapest flight booked recently is on American Airlines for just $196, but on average you can expect to pay $219.

Are there nonstop flights from Westchester County to Chicago for under $200 on Cheapflights?

Cheapflights has at least 20 direct flights from Westchester County to Chicago under $200. A good price for a nonstop flight from Westchester County to Chicago is less than $255.

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

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

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

Nonstop flights are available for this route on the following days: Monday, Tuesday.

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

On average 2 flights depart from Westchester County to Chicago per day.
Afternoon (Noon - 6pm) - 100% of flight departures

How long is the flight from Westchester County to Chicago?

A quick flight from Westchester County to Chicago can take about 2h 37m. American Airlines provides one of the quickest options available for as low as $196. There are 740 mi between Westchester County and Chicago. Both multi-stop and nonstop flights can be found to your destination and back.

What are the cheapest airlines to fly from Westchester County to Chicago one-way?

For one-way options, check prices for United Airlines. According to our data, you can fly for as low as $98. Users have also found prices from $106 and $107 on American Airlines and Delta, respectively.

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

When booking a flight from Westchester County to Chicago, you may want to consider flying on Undisclosed Carrier, American Airlines or JetBlue as they are the most popular for this route.

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

Consider Air Wisconsin (100%), United Airlines (92%) or Alaska Airlines (86%) when booking your flight. These represent the most reliable airlines when flying from Westchester County to Chicago.

What are the cheapest flights from Westchester County to Chicago?

Looking for the cheapest flight from Westchester County to Chicago? While on average our users pay $608, our data indicates the cheapest price to be $114. The most popular route (White Plains Westchester County - Chicago O'Hare Intl), is priced around $196.

Alternative routes for Westchester County to Chicago

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

Top 4 airlines flying from Westchester County to Chicago

The chart below displays the airlines Cheapflights users traveling from Westchester County to Chicago choose most often. Cheapest and average prices are based on aggregated data from the past 12 months.
AirlineCheapestAverageFlexibilityOn-timeCOVID-19 safety
Juneyao AirlinesCheapest$20Average$28FlexibilityNo cancel feeOn-time66%COVID-19 safety
Search Juneyao Airlines flights
United AirlinesCheapest$118Average$289FlexibilityNo cancel feeOn-time69%COVID-19 safety
Search United Airlines flights
American AirlinesCheapest$158Average$292FlexibilityNo cancel feeOn-time71%COVID-19 safety
Search American Airlines flights
DeltaCheapest$196Average$322FlexibilityNo cancel feeOn-timeN/ACOVID-19 safety
Search Delta flights

Hourly flight availability from Westchester County to Chicago

See what time of day planes typically take off from Westchester County to Chicago
10%of flight departuresEarly morningMidnight to 6 am
56%of flight departuresMorning6 am to noon
34%of flight departuresAfternoonNoon to 6 pm
0%of flight departuresEvening6 pm to midnight
Midnight
6 AM
Noon
6 PM