$129 Cheap Delta flights San Francisco (SFO) to Chicago (MDW)

Grab cheap round-trip Delta Air Lines flights from $237 from SFO to MDW by organizing your results from “Price (lowest to highest)” on Expedia. Or look for deals from $129 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.

Search for one-way or return flights to Chicago in January or February. You could find a cheap fare with Delta Air Lines during these quieter months.

Look for affordable Delta Air Lines flights from San Francisco Intl. Airport (SFO) to Midway Intl. Airport (MDW) one to three months prior to your departure date. 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 itinerary, the best day to book a domestic flight is usually Sunday and the most expensive day 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 out if there’s a direct trip from SFO to MDW with Delta Air Lines or another carrier, use our “Nonstop” filter when looking for flights.

Find Delta Air Lines’s earliest flights from SFO to MDW by using the “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.

Delta Air Lines flights from San Francisco Intl. Airport (SFO) to Chicago land at Midway Intl. Airport (MDW). This is the main entry point to this destination.

Offering a rewarding loyalty program and an excellent in-flight experience, Delta Air Lines is the leading choice for many travelers flying from SFO to MDW. Plus, if you’re a Delta SkyMiles and One Key™ member booking through Expedia, you could earn OneKeyCash™* on eligible flights on top of your airline miles, which can be spent on future getaways.*OneKeyCash™ disclaimer - OneKeyCash™ is not redeemable for cash and can only be used on Expedia, Hotels.com and Vrbo.

You can usually cancel or change your flight, although additional charges may apply if you made your booking over 24 hours ago. Want to keep your options open? Make use of Expedia’s “Changes included” and “No cancel fee” filters to find flights that won’t charge extra if you need to alter your plans. To make modifications, visit “Trips,” select your flight and click on “Manage Booking” for more information.