$129 Cheap Delta flights Oakland (OAK) to Chicago (ORD)

Make use of the "Price (lowest to highest)" filter on Expedia to look for cheap Delta Air Lines round-trip flights from $275 from OAK to ORD. Affordable one-way tickets from $129 are available too.**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 affordable Delta Air Lines flights from Oakland Intl. Airport (OAK) to O'Hare Intl. Airport (ORD) one to three months ahead of your departure. 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 type and itinerary, the ideal day to book a domestic flight is usually Sunday and the most expensive 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.

To find the earliest departures from OAK to ORD with Delta Air Lines, filter your search by "Morning" and "Early Morning." Booking 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.

Jetting off from OAK to ORD with Delta Air Lines comes with a host of benefits, such as an excellent in-flight experience and a rewarding loyalty program. Plus, when booking through Expedia, One Key™ members can earn OneKeyCash™* to spend on select future travel purchases. That's in addition to the Delta SkyMiles points you can earn with Delta Air Lines.*OneKeyCash™ disclaimer - OneKeyCash™ is not redeemable for cash and can only be used on Expedia, Hotels.com and Vrbo.