Cheap United flights New York (JFK) to Chicago (ORD)

You can discover cheap round-trip United Airlines flights from JFK to ORD by organizing your results from "Price (lowest to highest)" on Expedia. Or search for options for a one-way trip.**These prices were available on Expedia within the past 7 days, for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.

Look for cheap United Airlines flights from John F. Kennedy Intl. Airport (JFK) to O'Hare Intl. Airport (ORD) one to three months before your departure date. Travelers who book domestic flights 34 to 86 days in advance can save 25% compared to those who book just 6 to 12 days ahead. Regardless of fare class and itinerary, the ideal day to book a domestic flight is usually Sunday and the most expensive day tends to be Monday. Passengers who book on a Sunday can save 6% on average compared to those who book their travel on a Monday.**Ideal booking window recommendation is based on average round-trip ticket prices for January through November for 2024. Best day of the week to book recommendation is based on average round-trip ticket prices for January through October 2024. All data sourced from ARC's global airline sales database.

Sort your results by "Early Morning" and "Morning" to find the earliest flights from JFK to ORD. Taking off early means flight cancellations are less likely.**Most reliable time of the day recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.

A rewarding loyalty program and the ability to rack up points through United Mileage Plus are the start of the reasons to fly from JFK to ORD with United Airlines. Plus, when you join our One Key™ program, you can receive OneKeyCash™* in addition to United Airlines's loyalty program earnings. It's yours to use wherever your next trip takes you.*OneKeyCash™ disclaimer - OneKeyCash™ is not redeemable for cash and can only be used on Expedia, Hotels.com and Vrbo.