$286 Cheap Alaska Airlines flights Chicago (ORD) to Sitka (SIT)

Scoring cheap one-way Alaska Airlines flights from ORD to SIT from $286 on Expedia is easy — just filter by "Price (lowest to highest)." Alternatively, check out our budget-friendly return fares from $589 for your next break.**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 Alaska Airlines fares from O'Hare Intl. Airport (ORD) to Sitka Airport (SIT), 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 impact how much you pay. Sunday is usually the most affordable, 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.

Browse Alaska Airlines's earliest flights from ORD to SIT by checking our "Early Morning" and "Morning" filters. Not only will you get to your destination sooner, early departures are also 20% less likely to be 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.

Traveling from ORD to SIT with Alaska Airlines comes with a range of perks, such as a rewarding loyalty program and an excellent in-flight experience. Plus, when you book through Expedia, One Key™ members can collect OneKeyCash™* to use on select future travel purchases. That's on top of the Mileage Plan points you can earn with Alaska Airlines.*OneKeyCash™ disclaimer - OneKeyCash™ is not redeemable for cash and can only be used on Expedia, Hotels.com and Vrbo.