£470 Cheap Flights from White Plains (HPN) to Chicago (ORD)

View £470 flight on Thu, 4 Jun 2026Opens in a new window

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

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

Prices were available within the past 7 days and start at £470 for one-way flights and £732 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

JetBlue Airways
Fri, 5 Jun - Mon, 8 Jun
HPN
White Plains
ORD
Chicago
£732 Return, found 6 days ago
£732
Return
found 6 days ago
Select JetBlue Airways flight, departing Fri, 5 Jun from White Plains to Chicago, returning Mon, 8 Jun, priced at £732 found 6 days ago
JetBlue Airways
Thu, 4 Jun - Mon, 8 Jun
HPN
White Plains
ORD
Chicago
£797 Return, found 6 days ago
£797
Return
found 6 days ago
Select JetBlue Airways flight, departing Thu, 4 Jun from White Plains to Chicago, returning Mon, 8 Jun, priced at £797 found 6 days ago
JetBlue Airways
Thu, 4 Jun - Mon, 8 Jun
HPN
White Plains
ORD
Chicago
£804 Return, found 6 days ago
£804
Return
found 6 days ago
Select JetBlue Airways flight, departing Thu, 4 Jun from White Plains to Chicago, returning Mon, 8 Jun, priced at £804 found 6 days ago
JetBlue Airways
Thu, 11 Jun - Thu, 18 Jun
HPN
White Plains
ORD
Chicago
£824 Return, found 1 day ago
£824
Return
found 1 day ago
Select JetBlue Airways flight, departing Thu, 11 Jun from White Plains to Chicago, returning Thu, 18 Jun, priced at £824 found 1 day ago
JetBlue Airways
Fri, 5 Jun - Mon, 8 Jun
HPN
White Plains
ORD
Chicago
£844 Return, found 6 days ago
£844
Return
found 6 days ago
Select JetBlue Airways flight, departing Fri, 5 Jun from White Plains to Chicago, returning Mon, 8 Jun, priced at £844 found 6 days ago
JetBlue Airways
Wed, 17 Jun - Wed, 24 Jun
HPN
White Plains
ORD
Chicago
£864 Return, found 1 day ago
£864
Return
found 1 day ago
Select JetBlue Airways flight, departing Wed, 17 Jun from White Plains to Chicago, returning Wed, 24 Jun, priced at £864 found 1 day ago
JetBlue Airways
Fri, 12 Jun - Fri, 19 Jun
HPN
White Plains
ORD
Chicago
£876 Return, found 1 day ago
£876
Return
found 1 day ago
Select JetBlue Airways flight, departing Fri, 12 Jun from White Plains to Chicago, returning Fri, 19 Jun, priced at £876 found 1 day ago
JetBlue Airways
Wed, 17 Jun - Wed, 24 Jun
HPN
White Plains
ORD
Chicago
£889 Return, found 1 day ago
£889
Return
found 1 day ago
Select JetBlue Airways flight, departing Wed, 17 Jun from White Plains to Chicago, returning Wed, 24 Jun, priced at £889 found 1 day ago
JetBlue Airways
Thu, 4 Jun - Mon, 8 Jun
HPN
White Plains
ORD
Chicago
£895 Return, found 6 days ago
£895
Return
found 6 days ago
Select JetBlue Airways flight, departing Thu, 4 Jun from White Plains to Chicago, returning Mon, 8 Jun, priced at £895 found 6 days ago
JetBlue Airways
Thu, 4 Jun - Mon, 8 Jun
HPN
White Plains
ORD
Chicago
£902 Return, found 6 days ago
£902
Return
found 6 days ago
Select JetBlue Airways flight, departing Thu, 4 Jun from White Plains to Chicago, returning Mon, 8 Jun, priced at £902 found 6 days ago

Frequently asked questions

What is the cheapest month to fly from White Plains, NY (HPN-Westchester County) to Chicago, IL (ORD-O'Hare Intl.)?
February is typically the cheapest month to fly from White Plains, NY (HPN-Westchester County) to Chicago, IL (ORD-O'Hare Intl.), with average return fares of approximately £618. This is about 7% lower than the average price throughout the year. February often sees lower prices as it's outside of peak holiday travel and before the spring break rush, leading to less demand. Other cheap months to fly from White Plains, NY (HPN-Westchester County) to Chicago, IL (ORD-O'Hare Intl.) include March and September.
Which airlines fly direct from White Plains, NY (HPN-Westchester County) to Chicago, IL (ORD-O'Hare Intl.)?
Enter HPN to ORD and your travel dates, then apply the 'Nonstop' filter to see only direct flights.
How do I find cheap flights from White Plains, NY (HPN-Westchester County) to Chicago, IL (ORD-O'Hare Intl.)?
To find a cheap flight from White Plains, NY (HPN-Westchester County) to Chicago, IL (ORD-O'Hare Intl.), be flexible with your dates. Traveling outside of peak vacation months and booking a mid-week flight can help you save. Early morning and late night flights are often more affordable, too. Expedia allows you to compare flight times, airlines and routes all in one place to find low fares. You can also set up Price Tracking and receive alerts when fares go up or down.
What is the best airline to fly with from White Plains, NY (HPN-Westchester County) to Chicago, IL (ORD-O'Hare Intl.)?
The best airline to fly with from White Plains, NY (HPN-Westchester County) (HPN) to Chicago, IL (ORD-O'Hare Intl.) (ORD) will differ from traveller to traveller. If you like to fly early, AA offers early morning flights. If price is the most important factor, AA typically offers the lowest fares. AA offers the most daily flights from White Plains, NY (HPN-Westchester County) (HPN) to Chicago, IL (ORD-O'Hare Intl.) (ORD), which is brilliant if flexibility is what you value most. The best carrier for this journey could also be the one you have a loyalty membership with, as flying with that airline or another airline within the same alliance could help you collect points or enjoy lounge access.
What is the best time to fly from White Plains, NY (HPN-Westchester County) to Chicago, IL (ORD-O'Hare Intl.)?
The best time to find a good deal on a flight from White Plains, NY (HPN-Westchester County) to Chicago, IL (ORD-O'Hare Intl.) is typically February or September. Based on booking data from the past year, you can expect average return flight prices around £618 during these months. These periods often see lower demand, which can help you find more budget-friendly options for your trip.
How many flights per day from White Plains, NY (HPN-Westchester County) to Chicago, IL (ORD-O'Hare Intl.)?
When flying from White Plains, NY (HPN-Westchester County) to Chicago, IL (ORD-O'Hare Intl.), you'll find approximately 4 nonstop flights per day. For even more choice, look at flights that include layovers, as there are around 27 connecting flights per day. Some common connection points include Charlotte-Douglas Intl. (CLT), Ronald Reagan Washington National (DCA), and Hartsfield-Jackson Atlanta Intl. (ATL).
What is the earliest flight from White Plains, NY (HPN-Westchester County) to Chicago, IL (ORD-O'Hare Intl.)?
The earliest flight from White Plains, NY (HPN-Westchester County) (HPN) to Chicago, IL (ORD-O'Hare Intl.) (ORD) typically departs at approximately 5:50 AM local time, operated by American Airlines. This is a seasonal service active in October. An early departure like this can help maximise your time at your destination. To compare early flights on Expedia, select the "Early Morning" and "Morning" filters in your search.
What day of the week has the most flights from White Plains, NY (HPN-Westchester County) to Chicago, IL (ORD-O'Hare Intl.)?
If you're flying from White Plains, NY (HPN-Westchester County) to Chicago, IL (ORD-O'Hare Intl.), you'll typically find the most flight options on a Friday, with around 20 flights available. This gives you plenty of options to choose from for your travel plans. Major airlines on this route include American Airlines, Delta Air Lines, and Republic Airways. Flight schedules are consistent throughout the week, so you'll have a good selection of flights no matter when you choose to travel.
What are the most popular departure times for flights from White Plains, NY (HPN-Westchester County) to Chicago, IL (ORD-O'Hare Intl.)?
The most popular departure times for flights from White Plains, NY (HPN-Westchester County) to Chicago, IL (ORD-O'Hare Intl.) are in the early morning, from 6am to 9am. About 28% of passengers prefer this time window. Many major carriers, including American Airlines and Delta Air Lines, offer flights during this window. These early morning flights are often preferred by business travellers looking to get an early start to their day, or by leisure travellers who want to maximise their time at their destination.
How long does it take to fly from White Plains, NY (HPN-Westchester County) to Chicago, IL (ORD-O'Hare Intl.)?
A nonstop flight from HPN to ORD typically takes around 2 hours 50 minutes, covering approximately 736 miles. Connecting flights on this route usually add 4 hours 10 minutes to your travel time. Keep in mind that actual flight times can vary due to wind patterns, weather, and air traffic.
Can you fly business or first class from White Plains, NY (HPN-Westchester County) to Chicago, IL (ORD-O'Hare Intl.)?
Select the "Business class" and "First class" filters when looking for HPN to ORD flights on Expedia. This is the easiest way to compare prices, routes and flight times for your trip.
How do I earn miles on a White Plains, NY (HPN-Westchester County) to Chicago, IL (ORD-O'Hare Intl.) flight with Expedia?
It's easy to earn miles on a White Plains, NY (HPN-Westchester County) to Chicago, IL (ORD-O'Hare Intl.) flight when you book with Expedia. Before you confirm your booking, simply select your frequent flyer program and enter your program number. As a member of One Key™, you can also earn OneKeyCash™* on top of your airline miles when you book with Expedia. *Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.
What airports do you fly into for Chicago from Westchester County (HPN)?
From Westchester County (HPN), you can fly into O'Hare Intl. (ORD) and Midway Intl. (MDW) in Chicago. Some flights may connect through major hubs like Charlotte-Douglas Intl. (CLT), Ronald Reagan Washington National (DCA), Lebanon Municipal (LEB) before reaching Chicago. Compare routes and airports on Expedia to find the best flight options for your travel plans.
Is it cheaper to buy a plane ticket from White Plains, NY (HPN-Westchester County) to Chicago, IL (ORD-O'Hare Intl.) at the last minute?
Typically, booking a last minute flight from White Plains, NY (HPN-Westchester County) to Chicago, IL (ORD-O'Hare Intl.) will be more expensive than booking in advance. As the departure date approaches, there are usually fewer seats available which can drive up the cost. However, if there's some wiggle room with your travel dates and times, you could bag a cheap last-minute fare.
Is it cheaper to book a White Plains, NY (HPN-Westchester County) to Chicago, IL (ORD-O'Hare Intl.) flight and hotel package?
Securing a White Plains, NY (HPN-Westchester County) to Chicago, IL (ORD-O'Hare Intl.) flight and hotel package is usually cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels all in one place. Select from our extensive range of stays and then add flights, activities and car rentals to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from White Plains, NY (HPN-Westchester County) to Chicago, IL (ORD-O'Hare Intl.)?
If you booked your White Plains, NY (HPN-Westchester County) to Chicago, IL (ORD-O'Hare Intl.) flight within the last 24 hours, you may be able to modify or cancel it without any fees. Depending on the airline and the type of ticket you have, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal if you'd like more information.

Travel information

Origin airport
Westchester County
Destination airport
O'Hare Intl.
Return price
£732
Distance
1178 km
Average flight time
1 hour 50 mins

Book with confidence

Compare flights from White Plains to Chicago easily and book with confidence

For travelling on business or for pleasure, Expedia makes it easy to book your flights from White Plains to Chicago. Operating between them flights per day, 20 airlines cover the route. And fly direct, getting you to O'Hare Intl. in just hours. If you have a preferred carrier, use our advanced search tool to find the right flight from Westchester County to O'Hare Intl..  

To make things even better, in the advanced search, you can also choose to fly economy, premium economy, business or first class, select your maximum number of stops, and pick your preferred departure and arrival time. You can also opt for refundable and direct flights. 

Grab a great deal on your flight from Westchester County (HPN) to O'Hare Intl. (ORD)

The easiest way to view the best deals on flights from White Plains to Chicago today is to enter your travel dates and hit search. From here, you can sort your results by price to see the cheapest flights first. Right now, return flights from Westchester County to O'Hare Intl. start at just £732 and range up to £922.  

To find an even better deal, try  

  • being flexible on your dates – midweek flights can be cheaper
  • looking for other airports near White Plains and Chicago
  • booking your flight during June, the cheapest month on this route
  • varying your flight times – early morning and late at night are sometimes cheaper 

Why you should book your White Plains to Chicago flight with Expedia!

We cater for all flight types, cabin classes and airlines. So whether you’re booking flights from Westchester County to O'Hare Intl. for a budget break or a business trip with a bit of pleasure thrown in, we make it easy to secure the seat that’s right for you.  

Thanks to our supersized inventory that offers great choice all in one place, you know you’ll get a great deal with Expedia. Especially if you bundle your flight together with your hotel, you will unlock amazing savings. For added peace of mind, you can choose flexible bookings or filter to find refundable options, so you won’t pay a fee to change your flight.  

Compare flights from White Plains to Chicago easily and book with confidence

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*Available to Expedia members.