$149 Cheap Delta flights San Diego (SAN) to Chicago (ORD)

Grab affordable round-trip Delta Air Lines flights from $297 from SAN to ORD by filtering your results from “Price (lowest to highest)” on Expedia. Or look for deals from $149 for a one-way journey.**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.

Delta Air Lines flights to Chicago are often more affordable in the quieter months of January and February. Whether you’re searching for a return or one-way ticket, you could score a better deal then.

Search for affordable Delta Air Lines flights from San Diego Intl. Airport (SAN) to O’Hare Intl. Airport (ORD) one to three months ahead of your day of 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. Regardless of fare type and journey, the ideal day to book a domestic flight is generally 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.

Enter your dates, hit search and select “Nonstop” on Expedia to find any direct flights from SAN to ORD with Delta Air Lines or another carrier.

Search Delta Air Lines’s earliest flights from SAN to ORD by using the “Morning” and “Early Morning” filters. Not only will you arrive at 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.

Hop on a Delta Air Lines flight from San Diego Intl. Airport (SAN) to Chicago, and you’ll likely land at O’Hare Intl. Airport (ORD). This is the airline’s main hub in this city.

Delta Air Lines makes traveling from SAN to ORD enjoyable with an excellent in-flight experience and a rewarding loyalty program. You could even start earning points with Delta SkyMiles. Be sure to sign up to our free One Key™ rewards program to earn OneKeyCash™*, which can be redeemed on future trips.*OneKeyCash™ disclaimer - OneKeyCash™ is not redeemable for cash and can only be used on Expedia, Hotels.com and Vrbo.

In most cases, you can modify or cancel your flight, although additional fees may apply if your booking was made over 24 hours ago. Need to keep your options open? Apply the “Changes included” and “No cancel fee” filters to find flights that won’t charge you extra if you need to adjust your plans. To make changes, head to “Trips,” select your flight and click on “Manage Booking” for more details.