Users have found that booking a flight from Westchester County to Chicago at least 48 days early can save you up to 76% on average compared to booking a flight this week. If booking 48 days before your flight isn’t an option for you, users have found flights from Westchester County to Chicago for as little as $302 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 $415 for flights departing within the next 3 days.
Our data shows that February tends to be the cheapest month to fly to Chicago from Westchester County. Users have commonly found prices around $268 for the month, but tickets can be as low as $107. Due to multiple factors, prepare for potentially higher prices in June.
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.
Fly from
Fly to
Budget
$344 - $436
Route
Depart
Return
Price
White Plains Westchester CountyChicago Midway
HPN - MDW
HPNMDW
White Plains Westchester County
Wed 5/1
1 stop17h 04m
Chicago Midway
Sat 5/4
1 stop14h 29m
White Plains Westchester CountyChicago O'Hare Intl
HPN - ORD
HPNORD
White Plains Westchester County
Sat 5/4
1 stop18h 42m
Chicago O'Hare Intl
Tue 5/7
1 stop14h 15m
White Plains Westchester CountyChicago O'Hare Intl
HPN - ORD
HPNORD
White Plains Westchester County
Sat 5/4
1 stop18h 42m
Chicago O'Hare Intl
Tue 5/7
2 stops14h 07m
White Plains Westchester CountyChicago O'Hare Intl
HPN - ORD
HPNORD
White Plains Westchester County
Sat 5/4
2 stops14h 42m
Chicago O'Hare Intl
Tue 5/7
2 stops14h 07m
White Plains Westchester CountyChicago Midway
HPN - MDW
HPNMDW
White Plains Westchester County
Wed 5/1
1 stop17h 04m
Chicago Midway
Sat 5/4
1 stop14h 29m
White Plains Westchester CountyChicago Midway
HPN - MDW
HPNMDW
White Plains Westchester County
Sat 5/18
1 stop21h 46m
Chicago Midway
Mon 5/20
2 stops40h 15m
White Plains Westchester CountyChicago O'Hare Intl
HPN - ORD
HPNORD
White Plains Westchester County
Thu 4/11
Nonstop2h 31m
Chicago O'Hare Intl
Thu 4/11
2 stops17h 54m
White Plains Westchester CountyChicago O'Hare Intl
HPN - ORD
HPNORD
White Plains Westchester County
Wed 5/1
Nonstop2h 31m
Chicago O'Hare Intl
Sat 5/4
Nonstop2h 24m
White Plains Westchester CountyChicago O'Hare Intl
HPN - ORD
HPNORD
White Plains Westchester County
Tue 4/30
Nonstop2h 29m
Chicago O'Hare Intl
Fri 5/3
Nonstop2h 24m
No data available for this route at this time. Please check back soon.
Comfort
Boarding
Entertainment
Overall
Crew
Food
Reviews
In the boarding area at La Guardia, there are charging stations for electronics but the electric outlets do not work on many of the stations.
Comfort
Boarding
Entertainment
Overall
Crew
Food
Reviews
In the boarding area at La Guardia, there are charging stations for electronics but the electric outlets do not work on many of the stations.
Comfort
Boarding
Entertainment
Overall
Crew
Food
Reviews
In the boarding area at La Guardia, there are charging stations for electronics but the electric outlets do not work on many of the stations.
Comfort
Boarding
Entertainment
Overall
Crew
Food
Reviews
In the boarding area at La Guardia, there are charging stations for electronics but the electric outlets do not work on many of the stations.
1%of flight departures | Early morningMidnight to 6 am |
---|---|
67%of flight departures | Morning6 am to noon |
32%of flight departures | AfternoonNoon to 6 pm |
0%of flight departures | Evening6 pm to midnight |
Cheapflights helps you search for flights from Westchester County to Chicago via 900+ travel sites so you don’t have to. After performing a flight search, users can also filter their flight selection by filtering for price, number of stops, airlines, and so on.
By finding flights from multiple airlines and providers at completely no cost, Cheapflights helps millions of users like you annually find the best flights to Chicago from Westchester County.
Cheapflights does show flights with no change fees to all users. To see these options for flights from Westchester County to Chicago, users can toggle the no change fees filter when performing a flight search.
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Yes, you can often find last-minute deals on Westchester County to Chicago flights on Cheapflights. However, these deals can vary and may not always be available. We recommend checking back frequently or signing up for price alerts for the most up-to-date deals.
Cheapflights aggregates prices from various travel booking sites. This allows you to compare prices and choose the best deal.
Cancellation policies vary by airline and fare type. After entering your flight details, you can view the cancellation policies for each deal in the search results. Some deals may offer flexibility in terms of cancellation and changes.