$192 Cheap United flights Jackson (JAN) to Chicago (ORD)

Set the "Price (lowest to highest)" filter on Expedia to find cheap United Airlines round-trip flights from $373 from JAN to ORD. Affordable one-way tickets from $192 are available as well.**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.

To find cheap United Airlines fares from Evers Intl. Airport (JAN) to O'Hare Intl. Airport (ORD), start searching one to three months before your intended departure. Reserving domestic flights 34 to 86 days in advance could save you 25% compared to booking just 6 to 12 days ahead. The day you book can also impact the cost. Sunday is usually the cheapest, while Monday is often the most expensive for domestic flights. You can save 6% on average by booking your journey on a Sunday.**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.

Browse United Airlines's earliest flights from JAN to ORD by using our "Morning" and "Early Morning" filters. Not only will you arrive at your destination sooner, early departures also have a 20% less chance of being canceled.**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.

Offering a rewarding loyalty program, United Airlines is a favorite of many travelers heading from JAN to ORD. Plus, as a United Mileage Plus and One Key™ member booking through Expedia, you can earn OneKeyCash™* on eligible flights along with your airline miles.*OneKeyCash™ disclaimer - OneKeyCash™ is not redeemable for cash and can only be used on Expedia, Hotels.com and Vrbo.