$121 Cheap Flights from Chicago (ORD) to White Plains (HPN)

View $121 flight on Wed, Aug 6, 2025Opens in a new window

Popular airlines from Chicago O'Hare Intl. Airport (ORD) to Westchester County Airport (HPN)

Cheap Flights from Chicago to White Plains (ORD-HPN)

Prices were available within the past 7 days and start at $121 for one-way flights and $297 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Wed, Aug 13 - Wed, Aug 20
ORD
Chicago
HPN
White Plains
$297 Roundtrip, found 11 hours ago
$297
Roundtrip
found 11 hours ago
Select Delta flight, departing Wed, Aug 13 from Chicago to White Plains, returning Wed, Aug 20, priced at $297 found 11 hours ago
Delta
Tue, Oct 7 - Wed, Oct 15
ORD
Chicago
HPN
White Plains
$300 Roundtrip, found 6 hours ago
$300
Roundtrip
found 6 hours ago
Select Delta flight, departing Tue, Oct 7 from Chicago to White Plains, returning Wed, Oct 15, priced at $300 found 6 hours ago
Delta
Tue, Dec 2 - Tue, Dec 9
ORD
Chicago
HPN
White Plains
$303 Roundtrip, found 6 hours ago
$303
Roundtrip
found 6 hours ago
Select Delta flight, departing Tue, Dec 2 from Chicago to White Plains, returning Tue, Dec 9, priced at $303 found 6 hours ago
Delta
Tue, Sep 16 - Sat, Oct 4
ORD
Chicago
HPN
White Plains
$307 Roundtrip, found 20 hours ago
$307
Roundtrip
found 20 hours ago
Select Delta flight, departing Tue, Sep 16 from Chicago to White Plains, returning Sat, Oct 4, priced at $307 found 20 hours ago
Delta
Mon, Sep 15 - Sat, Sep 20
ORD
Chicago
HPN
White Plains
$310 Roundtrip, found 1 day ago
$310
Roundtrip
found 1 day ago
Select Delta flight, departing Mon, Sep 15 from Chicago to White Plains, returning Sat, Sep 20, priced at $310 found 1 day ago
Delta
Tue, Aug 26 - Sat, Aug 30
ORD
Chicago
HPN
White Plains
$312 Roundtrip, found 11 hours ago
$312
Roundtrip
found 11 hours ago
Select Delta flight, departing Tue, Aug 26 from Chicago to White Plains, returning Sat, Aug 30, priced at $312 found 11 hours ago
Delta
Tue, Aug 26 - Sun, Aug 31
ORD
Chicago
HPN
White Plains
$315 Roundtrip, found 11 hours ago
$315
Roundtrip
found 11 hours ago
Select Delta flight, departing Tue, Aug 26 from Chicago to White Plains, returning Sun, Aug 31, priced at $315 found 11 hours ago
Delta
Sat, Sep 13 - Sat, Sep 20
ORD
Chicago
HPN
White Plains
$317 Roundtrip, found 1 day ago
$317
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Sep 13 from Chicago to White Plains, returning Sat, Sep 20, priced at $317 found 1 day ago
American Airlines
Tue, Aug 5 - Tue, Aug 12
ORD
Chicago
HPN
White Plains
$349 Roundtrip, found 3 hours ago
$349
Roundtrip
found 3 hours ago
Select American Airlines flight, departing Tue, Aug 5 from Chicago to White Plains, returning Tue, Aug 12, priced at $349 found 3 hours ago
JetBlue Airways
Fri, Aug 15 - Mon, Aug 18
ORD
Chicago
HPN
White Plains
$459 Roundtrip, found 4 days ago
$459
Roundtrip
found 4 days ago
Select JetBlue Airways flight, departing Fri, Aug 15 from Chicago to White Plains, returning Mon, Aug 18, priced at $459 found 4 days ago

Find the cheapest month to fly from Chicago (ORD) to White Plains (HPN)

September is typically the cheapest month to fly

From $204 - $701 per traveler.

Graph displaying average flight prices per month

Flights from Chicago (ORD) to White Plains (HPN)
Origin airport
O'Hare Intl.
Destination airport
Westchester County
Airlines serving
American Airlines, Delta, JetBlue Airways
Roundtrip price
$297
Distance
736 mi
Average flight time
3 hours 17 mins

Chicago to White Plains Flights

The cheapest times to fly from Chicago to White Plains

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Chicago to White Plains are during the month of August. You can find some of the cheapest flights from Chicago to White Plains with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Chicago to White Plains

Sunday is one of the best days to book for cheap flights from Chicago to White Plains: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Chicago to White Plains

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Chicago to White Plains in 2025. You can also book with separate airlines for your outbound and return journeys, from $121 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Chicago to White Plains flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Chicago to White Plains airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Frequently asked questions

How much does a flight from O'Hare Intl. Airport (ORD) to Westchester County Airport (HPN) cost?
Discover the latest flight deals from ORD to HPN by entering your preferred travel dates and searching on Expedia. Easily compare prices by departure date if you have flexibility with your schedule and use handy filters to explore prices for your preferred journey. As a member of One Key™, our free loyalty program, you can use Price Tracking to watch fares and receive notifications if prices go up or down.
What is the cheapest month to fly from ORD to HPN?
Snap up a cheap ticket by booking your direct flight from ORD to HPN in August. You can find a one-way American Airlines flight for $246 leaving on August 31 2025. This price is based on the cheapest direct flight found on Expedia for this route in the next 330 days. The price was last updated on July 1 2025 and remains unchanged.
Which airlines fly direct from O'Hare Intl. Airport (ORD) to Westchester County Airport (HPN)?
You can fly directly from O'Hare Intl. Airport (ORD) to Westchester County Airport (HPN) on an American Airlines flight.
What is the cheapest airline that flies from ORD to HPN?
Travel from ORD to HPN with American Airlines. This carrier currently offers the cheapest one-way fare for this route, starting at $246. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from ORD on August 31 2025. Prices were last updated on July 1 2025 and have not changed since.
How many flights per day from O'Hare Intl. Airport (ORD) to Westchester County Airport (HPN)?
Each day on average, 3 direct flights take off from O'Hare Intl. Airport (ORD) to Westchester County Airport (HPN). Pick the departure time that best suits your plans.
What are the most popular departure times for flights from O'Hare Intl. Airport (ORD) to Westchester County Airport (HPN)?
More travelers fly between ORD and HPN at 8 AM than at any other time. Rather go when it's quieter? Travel outside of rush hours and there's a chance you'll save on your fare as well.
What day of the week has the most flights from ORD to HPN?
If you jet off on a Sunday, you'll get the widest range of choices for flights from O'Hare Intl. Airport (ORD) to Westchester County Airport (HPN).
What is the earliest flight from O'Hare Intl. Airport (ORD) to Westchester County Airport (HPN)?
Take the earliest flight at around 8:02AM UTC-6, heading out of O'Hare Intl. Airport (ORD). You'll be flying for around 2h 16m, arriving at Westchester County Airport (HPN) at approximately 11:18AM UTC-5.
How long does it take to fly from O'Hare Intl. Airport (ORD) to Westchester County Airport (HPN)?
The average flight duration from ORD to HPN is 2 hours and 13 minutes, covering a total distance of 740 mi.
What is the best time to fly from O'Hare Intl. Airport (ORD) to Westchester County Airport (HPN)?
Choose a flight from O'Hare Intl. Airport (ORD) to Westchester County Airport (HPN) that leaves before 3 PM to reduce the likelihood of delays. Departures after this hour are on average 22% more likely to be canceled.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports do you fly into for White Plains from O'Hare Intl. Airport (ORD)?
Board a direct flight from O'Hare Intl. Airport (ORD) to White Plains and you'll land at any one of these airports:

  • LaGuardia Airport (LGA)
  • Liberty Intl. Airport (EWR)
  • John F. Kennedy Intl. Airport (JFK)

Is it cheaper to buy a plane ticket from O'Hare Intl. Airport (ORD) to Westchester County Airport (HPN) last-minute?
Waiting until just before your trip to book a ticket from ORD to HPN often results in higher prices. Although you may find some last-minute offers, they aren't always guaranteed. Allow some flexibility in your schedule for the best chance of landing a bargain.
Is it cheaper to book an ORD to HPN flight and hotel package?
You'll typically save money by booking an ORD to HPN flight and hotel package compared to booking separately. In fact, travelers could save hundreds of dollars by bundling with Expedia. And it's easy to manage it all in one convenient place. Once you've selected your ideal flights and accommodations, consider adding extras such as activities, car rentals and tours.
Can I cancel or change the date of my flight from O'Hare Intl. Airport (ORD) to Westchester County Airport (HPN)?
If you reserved your ORD to HPN flight within the last 24 hours, you may be able to cancel or modify it without any fees. Depending on the airline and the fare type you purchased, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, visit our Customer Service portal for more information.

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*Available to One Key members.