$428 Cheap United flights Hilo (ITO) to Chicago (ORD)

Use the "Price (lowest to highest)" filter on Expedia to look for cheap United Airlines round-trip flights from $757 from ITO to ORD. Affordable one-way fares from $428 are also on offer.**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.

Search for affordable United Airlines flights from Hilo Intl. Airport (ITO) to O'Hare Intl. Airport (ORD) one to three months prior to your departure day. 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. No matter the fare class and itinerary, the best day to book a domestic flight is generally Sunday and the most expensive is typically 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.

Browse United Airlines's earliest flights from ITO to ORD by selecting our "Morning" and "Early Morning" filters. Not only will you get to where you're going sooner, early departures also experience 20% fewer cancellations.**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 passengers flying from ITO to ORD. Plus, as a United Mileage Plus and One Key™ member booking through Expedia, you could 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.