$129 Cheap Delta flights San Diego (SAN) to Chicago (MDW)

Make use of the “Price (lowest to highest)” filter on Expedia to search for cheap Delta Air Lines round-trip flights from $210 from SAN to MDW. Affordable one-way options 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.

January is one of the least expensive months to get away to Chicago with Delta Air Lines. You could also find great prices on return and one-way fares in February.

Start searching one to three months before your departure to find cheaper fares on Delta Air Lines flights from San Diego Intl. Airport (SAN) to Midway Intl. Airport (MDW). You can save 25% by booking your domestic flight 34 to 86 days in advance compared to last-minute reservations made 6 to 12 days out. You could also reduce costs by buying your fare on a Sunday, as it’s 6% cheaper on average than a Monday, the most expensive day to book.* Get your timing right, and you can enjoy significant savings on domestic flights.*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.

Fill in your dates, press search and select the “Nonstop” filter on Expedia to browse any direct flights from SAN to MDW with Delta Air Lines or another airline.

Browse Delta Air Lines’s earliest flights from SAN to MDW by using the “Morning” and “Early Morning” filters. Not only will you arrive at your destination 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 Diego Intl. Airport (SAN) to Chicago come in to Midway Intl. Airport (MDW). This is the main gateway here.

With a rewarding loyalty program and an excellent in-flight experience, Delta Air Lines is a top choice for many travelers heading from SAN to MDW. Also, 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 used 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 cancel or modify your flight, although additional charges may apply if you made your booking over 24 hours ago. Need to keep your options open? Use Expedia’s “Changes included” or “No cancel fee” filter to find flights that won’t charge extra if you have to alter your plans. To update your booking, go to “Trips,” select your flight and click on “Manage Booking” for further information.