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

View $121 flight on Mon, Aug 18, 2025Opens in a new window

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

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

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
Mon, Sep 8 - Tue, Sep 23
HPN
White Plains
ORD
Chicago
$297 Roundtrip, found 1 hour ago
$297
Roundtrip
found 1 hour ago
Select Delta flight, departing Mon, Sep 8 from White Plains to Chicago, returning Tue, Sep 23, priced at $297 found 1 hour ago
Delta
Wed, Aug 20 - Wed, Aug 27
HPN
White Plains
ORD
Chicago
$300 Roundtrip, found 7 hours ago
$300
Roundtrip
found 7 hours ago
Select Delta flight, departing Wed, Aug 20 from White Plains to Chicago, returning Wed, Aug 27, priced at $300 found 7 hours ago
Delta
Tue, Aug 12 - Sat, Aug 30
HPN
White Plains
ORD
Chicago
$302 Roundtrip, found 1 day ago
$302
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Aug 12 from White Plains to Chicago, returning Sat, Aug 30, priced at $302 found 1 day ago
Delta
Wed, Aug 20 - Thu, Aug 28
HPN
White Plains
ORD
Chicago
$303 Roundtrip, found 7 hours ago
$303
Roundtrip
found 7 hours ago
Select Delta flight, departing Wed, Aug 20 from White Plains to Chicago, returning Thu, Aug 28, priced at $303 found 7 hours ago
Delta
Wed, Aug 27 - Sat, Aug 30
HPN
White Plains
ORD
Chicago
$305 Roundtrip, found 1 day ago
$305
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, Aug 27 from White Plains to Chicago, returning Sat, Aug 30, priced at $305 found 1 day ago
Delta
Mon, Sep 8 - Sat, Sep 20
HPN
White Plains
ORD
Chicago
$307 Roundtrip, found 1 hour ago
$307
Roundtrip
found 1 hour ago
Select Delta flight, departing Mon, Sep 8 from White Plains to Chicago, returning Sat, Sep 20, priced at $307 found 1 hour ago
Delta
Wed, Aug 20 - Sat, Sep 6
HPN
White Plains
ORD
Chicago
$310 Roundtrip, found 7 hours ago
$310
Roundtrip
found 7 hours ago
Select Delta flight, departing Wed, Aug 20 from White Plains to Chicago, returning Sat, Sep 6, priced at $310 found 7 hours ago
Delta
Fri, Sep 5 - Tue, Sep 23
HPN
White Plains
ORD
Chicago
$312 Roundtrip, found 1 hour ago
$312
Roundtrip
found 1 hour ago
Select Delta flight, departing Fri, Sep 5 from White Plains to Chicago, returning Tue, Sep 23, priced at $312 found 1 hour ago
American Airlines
Sat, Aug 2 - Sat, Aug 9
HPN
White Plains
ORD
Chicago
$349 Roundtrip, found 5 hours ago
$349
Roundtrip
found 5 hours ago
Select American Airlines flight, departing Sat, Aug 2 from White Plains to Chicago, returning Sat, Aug 9, priced at $349 found 5 hours ago
JetBlue Airways
Fri, Aug 15 - Sun, Aug 17
HPN
White Plains
ORD
Chicago
$563 Roundtrip, found 7 hours ago
$563
Roundtrip
found 7 hours ago
Select JetBlue Airways flight, departing Fri, Aug 15 from White Plains to Chicago, returning Sun, Aug 17, priced at $563 found 7 hours ago

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

September is typically the cheapest month to fly

From $203 - $579 per traveler.

Graph displaying average flight prices per month

Flights from White Plains (HPN) to Chicago (ORD)
Origin airport
Westchester County
Destination airport
O'Hare Intl.
Airlines serving
American Airlines, Delta, JetBlue Airways
Roundtrip price
$297
Distance
736 mi
Average flight time
1 hour 34 mins

White Plains to Chicago Flights

The cheapest times to fly from White Plains to Chicago

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 White Plains to Chicago are during the month of September. You can find some of the cheapest flights from White Plains to Chicago with Expedia's search tool and vast selection of airlines.

 

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

Sunday is one of the best days to book for cheap flights from White Plains to Chicago: 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 White Plains to Chicago

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 White Plains to Chicago 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 White Plains to Chicago 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 White Plains to Chicago 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 Westchester County Airport (HPN) to O'Hare Intl. Airport (ORD) cost?
Cheap return flights from Westchester County Airport (HPN) to O'Hare Intl. Airport (ORD) start at $349. This information is based on the cheapest price found on Expedia for this return journey departing within the next three months. This airfare is for a American Airlines flight leaving HPN on July 30 2025 and touching down at ORD. The price was last updated on July 3 2025 and has not changed since.
What is the cheapest month to fly from HPN to ORD?
The cheapest flights from HPN to ORD are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
Which airlines fly direct from Westchester County Airport (HPN) to O'Hare Intl. Airport (ORD)?
You can fly straight from Westchester County Airport (HPN) to O'Hare Intl. Airport (ORD) on an American Airlines flight.
What is the cheapest airline that flies from HPN to ORD?
Use the filter tool on Expedia to compare airlines and find the cheapest carrier that'll take you from HPN to ORD. Sort your results by "Price (lowest to highest)" to snap up a great deal.
How many flights per day from Westchester County Airport (HPN) to O'Hare Intl. Airport (ORD)?
With an average of 3 direct flights departing from Westchester County Airport (HPN) to O'Hare Intl. Airport (ORD) every day, you'll be off on your next adventure in no time.
What are the most popular departure times for flights from Westchester County Airport (HPN) to O'Hare Intl. Airport (ORD)?
Flights between HPN and ORD tend to be busiest at 12 PM. If you want a less crowded experience and potentially cheaper fares, choose a departure outside the usual busy windows.
What day of the week has the most flights from HPN to ORD?
Travel on a Friday if you're looking for the best choice of flights from Westchester County Airport (HPN) to O'Hare Intl. Airport (ORD).
What is the earliest flight from Westchester County Airport (HPN) to O'Hare Intl. Airport (ORD)?
The earliest flight leaving Westchester County Airport (HPN) is at around 7:15AM UTC-5. Hop on this flight and you'll land at O'Hare Intl. Airport (ORD) at approximately 9:00AM UTC-6. The overall travel time is 2h 45m.
How long does it take to fly from Westchester County Airport (HPN) to O'Hare Intl. Airport (ORD)?
The average flight duration from HPN to ORD is 2 hours and 39 minutes, covering a distance of 740 mi.
What airline has the least delays from HPN to ORD?
With 100% of flights generally arriving on time, Qatar Airways has the best on-time performance for nonstop flights from Westchester County Airport (HPN) to O'Hare Intl. Airport (ORD). To monitor your flight status and receive notifications if anything changes, use the Expedia App.
What is the best time to fly from Westchester County Airport (HPN) to O'Hare Intl. Airport (ORD)?
Opt for a flight from Westchester County Airport (HPN) to O'Hare Intl. Airport (ORD) that leaves before 3 PM to reduce the risk of cancellations. 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 Chicago from Westchester County Airport (HPN)?
If you're boarding a direct flight from Westchester County Airport (HPN) to Chicago, O'Hare Intl. Airport (ORD) is the only airport you can touch down at.
Is it cheaper to buy a plane ticket from Westchester County Airport (HPN) to O'Hare Intl. Airport (ORD) last-minute?
Waiting until just before your trip to book a flight from HPN to ORD often results in higher prices. While you might find some last-minute offers, they're not always guaranteed. Allow some flexibility in your schedule for the best chance of getting a bargain.
Is it cheaper to book a HPN to ORD flight and hotel package?
Compared with arranging hotels and flights separately, booking a HPN to ORD flight and hotel package with Expedia could result in significant savings. Better yet, managing everything in one place will take the hassle out of planning your trip. Simply pick your flights and choose from our wide range of stays, then tailor your trip with other add-ons like car rentals and activities.
Can I cancel or change the date of my flight from Westchester County Airport (HPN) to O'Hare Intl. Airport (ORD)?
Typically, you can cancel or reschedule your HPN to ORD flight. However, additional fees may apply, especially if you made your booking over 24 hours ago. Double-check your itinerary for the airline's fees and policies on flight changes, or if you'd like more details, visit our Customer Service portal.

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*Available to One Key members.