$233 Cheap United flights Pierre (PIR) to Chicago (ORD)

Scoring cheap one-way United Airlines flights from PIR to ORD from $233 on Expedia couldn't be simpler — just filter by "Price (lowest to highest)." Or check out our affordable round-trip fares from $462 for your next exciting getaway.**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 Pierre Regional Airport (PIR) to O'Hare Intl. Airport (ORD), start searching one to three months before your planned 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 affect the overall price. Sunday is usually the cheapest, while Monday is often the most expensive for domestic flights. You can save 6% on average by booking your flight 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.

To find the earliest departures from PIR to ORD with United Airlines, sort your results by "Early Morning" and "Morning." Choosing an early flight generally means you'll experience 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 top pick for many travelers departing from PIR 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.