$143 Cheap Flights from White Plains (HPN) to Chicago (ORD)

View $143 flight on Wed, Dec 31, 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 $143 for one-way flights and $338 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Thu, Dec 11 - Tue, Dec 16
HPN
White Plains
ORD
Chicago
$338 Roundtrip, found 3 days ago
$338
Roundtrip
found 3 days ago
Select Delta flight, departing Thu, Dec 11 from White Plains to Chicago, returning Tue, Dec 16, priced at $338 found 3 days ago
American Airlines
Wed, Dec 31 - Thu, Jan 1
HPN
White Plains
ORD
Chicago
$349 Roundtrip, found 1 day ago
$349
Roundtrip
found 1 day ago
Select American Airlines flight, departing Wed, Dec 31 from White Plains to Chicago, returning Thu, Jan 1, priced at $349 found 1 day ago
Delta
Tue, Jan 13 - Sun, Jan 18
HPN
White Plains
ORD
Chicago
$353 Roundtrip, found 1 hour ago
$353
Roundtrip
found 1 hour ago
Select Delta flight, departing Tue, Jan 13 from White Plains to Chicago, returning Sun, Jan 18, priced at $353 found 1 hour ago
Delta
Mon, Dec 8 - Thu, Dec 25
HPN
White Plains
ORD
Chicago
$356 Roundtrip, found 5 days ago
$356
Roundtrip
found 5 days ago
Select Delta flight, departing Mon, Dec 8 from White Plains to Chicago, returning Thu, Dec 25, priced at $356 found 5 days ago
Delta
Thu, Feb 5 - Mon, Feb 9
HPN
White Plains
ORD
Chicago
$358 Roundtrip, found 3 days ago
$358
Roundtrip
found 3 days ago
Select Delta flight, departing Thu, Feb 5 from White Plains to Chicago, returning Mon, Feb 9, priced at $358 found 3 days ago
American Airlines
Wed, Dec 31 - Thu, Jan 1
HPN
White Plains
ORD
Chicago
$359 Roundtrip, found 1 day ago
$359
Roundtrip
found 1 day ago
Select American Airlines flight, departing Wed, Dec 31 from White Plains to Chicago, returning Thu, Jan 1, priced at $359 found 1 day ago
Delta
Fri, Jan 16 - Sat, Jan 17
HPN
White Plains
ORD
Chicago
$361 Roundtrip, found 1 hour ago
$361
Roundtrip
found 1 hour ago
Select Delta flight, departing Fri, Jan 16 from White Plains to Chicago, returning Sat, Jan 17, priced at $361 found 1 hour ago
Delta
Wed, Feb 18 - Mon, Feb 23
HPN
White Plains
ORD
Chicago
$363 Roundtrip, found 4 days ago
$363
Roundtrip
found 4 days ago
Select Delta flight, departing Wed, Feb 18 from White Plains to Chicago, returning Mon, Feb 23, priced at $363 found 4 days ago
Delta
Sat, Dec 13 - Wed, Dec 31
HPN
White Plains
ORD
Chicago
$366 Roundtrip, found 14 hours ago
$366
Roundtrip
found 14 hours ago
Select Delta flight, departing Sat, Dec 13 from White Plains to Chicago, returning Wed, Dec 31, priced at $366 found 14 hours ago
Delta
Wed, Mar 25 - Tue, Apr 14
HPN
White Plains
ORD
Chicago
$369 Roundtrip, found 2 hours ago
$369
Roundtrip
found 2 hours ago
Select Delta flight, departing Wed, Mar 25 from White Plains to Chicago, returning Tue, Apr 14, priced at $369 found 2 hours ago

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

November is typically the cheapest month to fly

From $263 - $644 per traveler.

Alternative airports near Chicago

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Midway Intl. MDW. Closest option available. Average driving time to city center is 16 minutes. Flights from $543
MDW
Midway Intl.
Closest
Average driving time to city center16 min
Flights from $543

Frequently asked questions

How much does a flight from Westchester County Airport (HPN) to O'Hare Intl. Airport (ORD) cost?
Secure a cheap one-way flight from $143 or cheap return flight from $338 from Westchester County Airport (HPN) to O'Hare Intl. Airport (ORD) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight offers on this route.
What is the cheapest month to fly from Westchester County Airport (HPN) to O'Hare Intl. Airport (ORD)?
The cheapest month to fly from HPN to ORD is December, when there's less demand. Off-peak months are generally when you'll find lower airfares between these airports.
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 Westchester County Airport (HPN) to O'Hare Intl. Airport (ORD)?
Use the filter tool on Expedia to compare different airlines and find the cheapest carrier that'll take you from HPN to ORD. Then, sort your results by "Price (lowest to highest)" to pick up a good 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.

Travel information

Origin airport
Westchester County
Destination airport
O'Hare Intl.
Airlines serving
American Airlines, Delta
Roundtrip price
$338
Distance
736 mi
Average flight time
1 hour 45 mins

Book with confidence

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 December. 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 $143 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.

 

White Plains to Chicago Flights

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*Available to One Key members.