Cheap flights from Illinois to Westchester County

ORD — HPN
Oct 10 — Oct 171

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

Travelers have found it’s best to book a flight 43 days in advance to save up to 66% compared to booking the same week of travel. As your travel date approaches, the cost of this flight route may potentially increase. While opting to book 43 days out may not be an option for all, there are still additional ways to secure a deal in the near future. You might find a flight from Illinois to Westchester County 1-2 weeks in advance for as low as $247, or $304 for flights within the next 24 hours.

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

Our data shows that January tends to be the cheapest month to fly to Westchester County from Illinois. Users have commonly found prices around $217 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 Illinois to Westchester County (IL - REU)?

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

Cheap flights from Illinois to Westchester County in October, November 2022

The best prices found for Illinois to Westchester County flights for October, November
Nov 11 - Nov 14
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
$208

United Airlines

Pick Dates

Deal found 10/3/22

Nov 5 - Nov 7
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 38m
$215

American Airlines

Pick Dates

Deal found 10/3/22

Nov 4 - Nov 6
ORD

Chicago O'Hare Intl

HPN

White Plains Westchester County

Nonstop

2h 07m
HPN

White Plains Westchester County

ORD

Chicago O'Hare Intl

1 stop

6h 25m
$217

American Airlines

Pick Dates

Deal found 10/2/22

Illinois to Westchester County 2022 flight deals

Cheap flights to Westchester County from Illinois found for this year
Nov 11 - Nov 14
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
$208

United Airlines

Pick Dates

Deal found 10/3/22

Dec 2 - Dec 4
ORD

Chicago O'Hare Intl

HPN

White Plains Westchester County

1 stop

7h 41m
HPN

White Plains Westchester County

ORD

Chicago O'Hare Intl

Nonstop

2h 36m
$215

American Airlines

Pick Dates

Deal found 10/3/22

Nov 4 - Nov 6
ORD

Chicago O'Hare Intl

HPN

White Plains Westchester County

Nonstop

2h 07m
HPN

White Plains Westchester County

ORD

Chicago O'Hare Intl

1 stop

6h 25m
$217

American Airlines

Pick Dates

Deal found 10/2/22

Cheap American Airlines flights from Illinois to Westchester County

Dec 2 - Dec 4
ORD

Chicago O'Hare Intl

HPN

White Plains Westchester County

1 stop

7h 41m
HPN

White Plains Westchester County

ORD

Chicago O'Hare Intl

Nonstop

2h 36m
$215

American Airlines

Pick Dates

Deal found 10/3/22

Nov 4 - Nov 6
ORD

Chicago O'Hare Intl

HPN

White Plains Westchester County

Nonstop

2h 07m
HPN

White Plains Westchester County

ORD

Chicago O'Hare Intl

1 stop

6h 25m
$217

American Airlines

Pick Dates

Deal found 10/2/22

Jan 19 - Jan 23
ORD

Chicago O'Hare Intl

HPN

White Plains Westchester County

1 stop

5h 10m
HPN

White Plains Westchester County

ORD

Chicago O'Hare Intl

1 stop

5h 17m
$223

American Airlines

Pick Dates

Deal found 10/3/22

Cheap Delta flights from Illinois to Westchester County

Dec 1 - Dec 4
MDW

Chicago Midway

HPN

White Plains Westchester County

1 stop

5h 47m
HPN

White Plains Westchester County

MDW

Chicago Midway

1 stop

5h 05m
$226

Delta

Pick Dates

Deal found 10/4/22

Jan 19 - Jan 22
MDW

Chicago Midway

HPN

White Plains Westchester County

1 stop

3h 59m
HPN

White Plains Westchester County

MDW

Chicago Midway

1 stop

3h 51m
$235

Delta

Pick Dates

Deal found 10/3/22

Nov 2 - Nov 2
ORD

Chicago O'Hare Intl

HPN

White Plains Westchester County

1 stop

4h 59m
HPN

White Plains Westchester County

ORD

Chicago O'Hare Intl

1 stop

4h 01m
$244

Delta

Pick Dates

Deal found 10/3/22

Non-stop flights to Westchester County from Illinois

Save time with Illinois to Westchester County direct flight deals
Nov 11 - Nov 14
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
$208

United Airlines

Pick Dates

Deal found 10/3/22

Nov 1 - Nov 1
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
$225

American Airlines

Pick Dates

Deal found 10/4/22

Nov 2 - Nov 2
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
$226

American Airlines

Pick Dates

Deal found 10/3/22

Last minute flights from Illinois to Westchester County

Late deals on return flights to Westchester County from Illinois, departing today and this week
Oct 11 - Nov 3
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 10/4/22

Oct 15 - Oct 21
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
$328

United Airlines

Pick Dates

Deal found 10/2/22

Oct 15 - Oct 16
ORD

Chicago O'Hare Intl

HPN

White Plains Westchester County

1 stop

7h 37m
HPN

White Plains Westchester County

ORD

Chicago O'Hare Intl

Nonstop

2h 34m
$335

American Airlines

Pick Dates

Deal found 10/2/22

One-way flights to Westchester County from Illinois

The cheapest one-way flights from Illinois to Westchester County
Oct 26
ORD

Chicago O'Hare Intl

HPN

White Plains Westchester County

2 stops

15h 25m
$110

Multiple Airlines

Pick Dates

Deal found 10/2/22

Oct 26
ORD

Chicago O'Hare Intl

HPN

White Plains Westchester County

Nonstop

2h 12m
$113

American Airlines

Pick Dates

Deal found 10/2/22

Nov 2
MDW

Chicago Midway

HPN

White Plains Westchester County

2 stops

21h 51m
$119

Multiple Airlines

Pick Dates

Deal found 10/4/22

Related info for your journey

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

Which airlines flying from Illinois to Westchester County 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 Illinois to Westchester County for under $300 on Cheapflights?

Yes, there are multiple flights from Illinois to Westchester County for under $300. The cheapest flight booked recently is on United Airlines for just $208, but on average you can expect to pay $229.

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

Cheapflights has at least 20 direct flights from Illinois to Westchester County under $300. A good price for a nonstop flight from Illinois to Westchester County is less than $294.

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

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

Flights to Westchester County from Illinois

Destination points for flights from Illinois to Westchester County

Select to see more specific information for flights from Illinois to all places in Westchester County

Top 3 airlines flying from Illinois to Westchester County

The chart below displays the airlines Cheapflights users traveling from Illinois 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$377FlexibilityNo cancel feeOn-time71%COVID-19 safety
Search American Airlines flights
United AirlinesCheapest$162Average$290FlexibilityNo cancel feeOn-time69%COVID-19 safety
Search United Airlines flights

Hourly flight availability from Illinois to Westchester County

See what time of day planes typically take off from Illinois 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