S$500 Cheap Flights from White Plains to Chicago

View S$500 flight on Sun, 1 Feb, 2026Opens in a new window

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

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

Prices were available within the past 7 days and start at S$500 for one-way flights and for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

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

May is typically the cheapest month to fly

From S$342 - S$751 per traveller.
White Plains to Chicago route information
Origin airport
Westchester County
Destination airport
O'Hare Intl.
Distance
1178 km
Average flight time
1 hour 47 mins

Perfect flights from White Plains to Chicago

Your Journey from White Plains to Chicago

Start your unforgettable journey with Expedia. Our broad selection of flights from White Plains to Chicago caters to every travel need. Whether you're yearning for a romantic escape, a solo adventure, or a cultural immersion, we've got you covered.
 

Choosing Your Ideal Flight

With Expedia, you have access to a wide range of airlines, including Delta, American Airlines, Cape Air. Our selection of flights from Westchester County to O'Hare Intl. caters to every traveler's requirements, ensuring your journey aligns with your schedule. With options from 20 airlines, you're bound to find the perfect flight.
 

Maximizing Value with White Plains to Chicago Flights

Experience the joy of finding cheap flights from Westchester County to O'Hare Intl. that fit your budget. Keep an eye out for our special deals and discounts, and check our flexible one-way fares from S$500 and roundtrip prices *.
 

Pre-Flight Essentials

Ensure a smooth journey from White Plains to Chicago with Expedia. From information about check-in times and in-flight amenities to guidance on baggage policies, we provide all the essentials to prepare you for your flight.
 

Experience the Vibrant Chicago

Picture yourself stepping off the plane in Chicago and immersing yourself in the unique atmosphere of . From local markets to cultural festivals, each city offers its distinct charm. Make the most of your trip by exploring local attractions and indulging in the local cuisine. With Expedia, explore all this and more, tailored to your budget.
 

Added Convenience on Your White Plains to Chicago Flight

Traveling with Expedia is more than just a flight. We offer details about in-flight amenities, baggage policies, and more to ensure a smooth and hassle-free journey. Choose from our variety of airlines and embark on a memorable journey from White Plains to Chicago.
 

Beyond the Flight – Exploring Chicago

With Expedia, your adventure extends beyond the flight. Explore Chicago at your own pace by renting a car or booking a hotel. Discover hidden gems off the beaten path and create unforgettable memories.
 

Book Your Flight from White Plains to Chicago with Confidence

Planning your next great adventure is a breeze with Expedia. Our user-friendly platform, unbeatable prices, and round-the-clock customer support make your travel experience seamless and stress-free. Embark on your journey from White Plains to Chicago with confidence. Book your travel arrangements with Expedia today.
 
*Note: Prices may vary based on availability and are subject to change.

Frequently asked questions

How much is a flight from HPN to O'Hare Intl. Airport (ORD)?
Within the past 7 days on Expedia, for flights departing within the next year, the lowest price listed for a round-trip flight between Westchester County Airport (HPN) and O'Hare Airport was . Cheap tickets don't last long, so make sure you book yours ASAP. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from Westchester County Airport (HPN) to ORD?
When it comes to cancellation fees, every airline has its own terms and conditions. If you decide to cancel your trip, visit our Customer Service Portal.
How do I find cheap flights from White Plains Airport to ORD that have flexible change policies?
Many airlines offer the option to reschedule your flight without a change fee. All you pay is the difference between the original flight and the new flight. When you're searching for HPN to ORD flights, you'll see a "no change fees" filter for you to select.
How far is the flight from Westchester County Airport (HPN) to O'Hare Airport?
That new movie you've been desperate to see will have to wait — the flight distance between HPN and ORD is only 1,200 kilometres. The captain will be instructing you to put your seat upright for landing before you know it.
Which airlines fly direct from White Plains Airport to ORD?
American Airlines (AA) is the number one choice for many travellers. It offers 91 flights between HPN and ORD each month. You could also take a look at the fares available with United Airlines (UA). This carrier operates 91 flights a month between West Harrison and Chicago.
Are White Plains Airport to O'Hare Airport flight tickets cheaper when they're purchased at the last minute?
It is possible to find great last-minute deals from Westchester County Airport (HPN) to O'Hare Intl. Airport (ORD), but it's also possible to miss out entirely! As many airlines advertise prices up to a year in advance, it's worthwhile keeping an eye on fares early and being ready to pounce when you spot a bargain. Expedia compares air carrier prices and updates flight deals all the time, so you can be sure you're always seeing the latest offers.

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