£207 Cheap Flights from White Plains (HPN) to Chicago (ORD)

You can find one-way and return flights from HPN to ORD with Expedia. Flight prices vary based on the month and day of the week you want to travel, as well as the airline and how far in advance you book your ticket. Filter your search on Expedia by "Price (lowest to highest)" to see our cheapest fares first, and use the Price Tracking tool to receive alerts when HPN to ORD ticket fares go up or down.

The cheapest months to fly from White Plains, NY (HPN) to Chicago, IL (ORD) are typically during off-peak season when demand is low. Traveling in off-peak or shoulder months is usually a good way to secure cheap tickets, just remember to avoid flying during holidays if you are able to. Use the calendar view in your search to see which months have low fares on this route.

Only one airline offers direct flights from White Plains, NY (HPN-Westchester County) to Chicago, IL (ORD-O'Hare Intl.). American Airlines operates 34 direct flights from HPN to ORD every week.

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.

The best airline to fly with from White Plains, NY (HPN-Westchester County) to Chicago, IL (ORD-O'Hare Intl.) will differ from traveler to traveler. If you like to fly early, American Airlines offers early morning flights. If price is the most important factor, American Airlines typically offers the lowest fares. American Airlines offers the most daily flights from White Plains, NY (HPN-Westchester County) to Chicago, IL (ORD-O'Hare Intl.), which is great 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.

The cheapest months to fly from White Plains, NY (HPN-Westchester County) to Chicago, IL (ORD-O'Hare Intl.) are typically February and September, with average return flights costing around £333. These months often offer a good balance of more affordable fares and generally fewer crowds, making them ideal for a more relaxed trip.

You'll find approximately 5 nonstop flights per day from White Plains, NY (HPN-Westchester County) to Chicago, IL (ORD-O'Hare Intl.). For even more choices, look at flights that include layovers, as there are around 16 connecting flights per day. Some common connection points include Charlotte-Douglas Intl. (CLT), Ronald Reagan Washington National (DCA), and Hartsfield-Jackson Atlanta Intl. (ATL).

The earliest flight from White Plains, NY (HPN-Westchester County) to Chicago, IL (ORD-O'Hare Intl.) typically departs around 5:50 AM. This service is operated by American Airlines. It's a seasonal service, active only in October. An early departure like this can be really convenient, allowing you to arrive in Chicago with plenty of time to start your day. To compare early flights on Expedia, select the "Early Morning" and "Morning" filters in your search.

You'll typically find the most flights from White Plains, NY (HPN-Westchester County) to Chicago, IL (ORD-O'Hare Intl.) on a Friday, with around 21 flights available. This gives you a good selection of options for your travel plans. Major airlines on this route include American Airlines, Delta, and Cape Air. Flight schedules are fairly consistent throughout the week, with Friday offering only slightly more options than other days.

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. Many major carriers, including American Airlines, Delta and JetBlue Airways, offer flights during this window. Many travellers prefer these times because it allows for an early arrival at your destination, giving you more of the day to enjoy.

A non-stop flight from White Plains, NY (HPN-Westchester County) to Chicago, IL (ORD-O'Hare Intl.) typically takes around 2 hours 48 minutes, covering a distance of about 1,184 kilometers. If you opt for a flight with one stop, your journey will usually be longer, taking around 7 hours 30 minutes. Flights with two or more stops generally take about 9 hours. Keep in mind that actual flight times can vary due to factors like wind patterns and air traffic, so it's always a good idea to allow for some extra time when planning your trip.

Yes, you can fly business class or first class between HPN and ORD. You can fly business class with Delta.

First class cabins are available on Delta and American Airlines.

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.

If you're planning to travel to Chicago from Westchester County (HPN), you can fly directly into O'Hare Intl. (ORD). Some flights may connect through major hubs like Charlotte-Douglas Intl. (CLT), Ronald Reagan Washington National (DCA), or Lebanon Municipal (LEB) before reaching Chicago. Compare routes and airports on Expedia to find the best flight options for your travel plans.

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.

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.

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.