Cheap Flights from Chicago (CHIA) to Westchester County (HPN)

Compare Chicago to Westchester County flight deals

Find the cheapest month or even day of the year to fly to Westchester County

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Flight deals from Chicago to Westchester County

Looking for a cheap last-minute deal or the best return flight from Chicago to Westchester County Airport? If you want to travel next month, return fares start from £271. Find the lowest prices on one-way and return tickets right here.

Find the cheapest month to fly from Chicago to Westchester County

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Chicago to Westchester County flights are currently cheapest in May.

Direct flights from Chicago to Westchester County

Chicago to White Plains: Flight information

The things to know before you go.
Cheapest flight found£93
Cheapest month to flyMay
Average flight time2 hrs, 19 mins
Most popular airlineEnvoy Air
Average flights per week108

Finding cheap flights from Chicago to Westchester County: Frequently asked questions

The best price we found for a return flight from Chicago to Westchester County is £271. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
2 hours and 19 minutes is the average flight time from Chicago to Westchester County.
Envoy Air, American Airlines and Alaska Airlines fly direct from Chicago to Westchester County.
As of April 2026, there are 108 flights per week flying from Chicago to Westchester County.
The cheapest month to fly from Chicago to Westchester County is usually May.
After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Chicago to Westchester County Airport on Saturday, 9 May 2026.
Yes – the average flight time is 2 hours and 19 minutes.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Westchester County but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.
We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to White Plains is around 40 days in advance, so don’t leave your flight to the last minute.

Travelling from Chicago to Westchester County Airport (HPN): What you need to know

  • Start planning your holiday by checking out the most convenient departure point for your flight from Chicago to Westchester County Airport (HPN). Explore the options for setting off from O'Hare International Airport (ORD) or Chicago Midway International Airport (MDW), two of the city's main airports.

  • The average duration of a direct Chicago to Westchester County Airport flight is 2 hours 15 minutes.

  • The timezone in White Plains is UTC-4, which is one hour ahead of Chicago. Westchester County Airport is located in White Plains.

  • The most popular route is from O'Hare International Airport (ORD) to Westchester County Airport (HPN), with 25 direct weekly services. If you're eager to be on your way, the earliest flight from ORD to HPN is the 8am American Airlines option. If you're looking to take off later, the final departure is at 8:10pm with American Airlines.

  • Your flight from Chicago to HPN won't wait if you're late, so show up at the airport on time. Arrive up to one hour in advance for domestic flights and two hours ahead for international travel.

  • If you're heading away during a major holiday or other peak period, give yourself more time. Get there two hours ahead of domestic flights and up to four hours before international departures. Lines at security and check-in will be longer.

Airports in Chicago

O'Hare International Airport (ORD)

  • You can take a direct flight from Chicago to Westchester County Airport (HPN) out of O'Hare International Airport (ORD).

  • American Airlines is a well-known carrier that offers direct flights from Chicago to Westchester County Airport jetting out of ORD.

  • Most passengers prefer to fly with American Airlines between ORD and HPN.

  • The carrier with the best on-time performance on this route is American Airlines. Its services arrive as scheduled 76.51% of the time.

  • ORD is around 40 kms (25 miles) from central Chicago. If you're catching a cab, ride-sharing or driving from the centre, it'll take 35 minutes or so to get there, depending on traffic conditions. If you're using public transport, expect the travel time to be around 55 minutes.

  • Catching an early flight from Chicago to Westchester County Airport? Avoid the last-minute rush to the terminal (and sneak in some extra precious sleep) by choosing one of these hotels close to O'Hare International Airport:

  • When it comes to the on-time performance of O'Hare International Airport, data shows 74.85% of flights arrive within the expected time frame.

  • You'll find ORD at 10000 West O'Hare.

Chicago Midway International Airport (MDW)

  • On public transport, you can travel from central Chicago to MDW in around 45 minutes. The terminal is roughly 19 kms (12 miles) away, and making the journey by car will take approximately 20 minutes.

  • Flying off with the first light? You might like to check in to one of these hotels near Chicago Midway International Airport the day before your Chicago to HPN flight:

  • Chicago Midway International Airport has an on-time performance of 77.88%. This figure highlights how often flights that depart from this airport arrive on time.

  • You'll find MDW at 5700 South Cicero.

Chicago Rockford International Airport (RFD)

  • RFD is around 137 kms (85 miles) from central Chicago. The drive from the city centre to the terminal takes about 1 hour 25 minutes. If you're considering public transport, expect a journey of around 4 hours 15 minutes.

  • Set yourself up for a smooth departure — stay close to Chicago Rockford International Airport and know you'll get to your boarding gate with time to spare. Settle in at one of these hotels the day before if you have an early Chicago to Westchester County Airport flight:

  • Flights that depart from RFD make it to their destination on schedule 76.19% of the time.

  • The address of Chicago Rockford International Airport is 2 Airport Cir.

About Westchester County Airport (HPN)

  • Coming in on a late flight from Chicago to Westchester County Airport? Don't let it hijack your sleep schedule. Stay within easy reach of HPN at Sonesta White Plains Downtown.

  • Say yes to new adventures by picking up a Westchester County Airport rental car. Grab your wheels from Dollar, Thrifty or Hertz and explore beyond White Plains's main sights.

  • Lock in the lowest price by reserving your ride around one week ahead of your Chicago to Westchester County Airport flight.

  • The address for HPN is 240 Airport Road, Suite 202.

How to find the cheapest flights from Chicago to Westchester County Airport (HPN)

  • The cheapest price we've found for a one-way ticket from Chicago to Westchester County Airport is £93. For a return flight on this route, the best price is £271. Depending on when and how early you book, these fares may change.

  • Booking ahead of time is often the key to scoring a cheap flight from Chicago to HPN. Fares tend to rise as demand increases, so the closer your departure date, the more it could cost you.

  • If you can be flexible with your travel plans, use the 'Whole month' tool. It'll show you the cheapest price across every month when searching for your Chicago to Westchester County Airport ticket.

  • Save time searching for cheap plane tickets from Chicago to HPN by creating a Price Alert. We'll send you an email or push notification on the app when fares go down.

  • Filters make it easier to land a deal on your flight from Chicago to Westchester County Airport. Choose the flight times, carriers and stops that make sense for you. Then sort the results by 'Cheapest' to find the best price quickly.

The best time to fly from Chicago to Westchester County Airport (HPN)

  • Picture the kind of break you want when planning your trip dates. May is the quietest month to go to White Plains. August is when most people book flights from Chicago to Westchester County Airport (HPN), which may be ideal if you're chasing more excitement.

  • The warmest month in White Plains is July, with temperatures ranging between 17ºC (63ºF) and 31ºC (88ºF). Book your Chicago to HPN plane ticket then if this is the type of weather you enjoy.

  • Search for cheap tickets from Chicago to Westchester County Airport in January if you like travelling in cooler conditions. Temperatures are at their lowest then, ranging between -7ºC (19ºF) and 7ºC (45ºF).

More about White Plains

Explore more of the United States

  • Philadelphia is just one of the many cities in the United States waiting to be explored after you've seen White Plains. Around 177 kms (110 miles) away to the south-west, its top attractions include Independence Hall, Liberty Bell and Philadelphia Museum of Art.

  • Around 257 kms (160 miles) north-east of White Plains, Boston is another essential stop in the United States. Experience this destination's highlights firsthand at Museum of Fine Arts Boston, Freedom Trail and Quincy Market.

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.