$129 Cheap Delta flights Washington (DCA) to Chicago (MDW)

Landing cheap one-way Delta Air Lines flights from DCA to MDW from $129 on Expedia is simple — just filter by "Price (lowest to highest)." Alternatively, check out our affordable round-trip fares from $157 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.

Start searching one to three months ahead of your travel date to score cheap fares on Delta Air Lines flights from Ronald Reagan Washington National Airport (DCA) 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 spot on, and you can enjoy significant savings on domestic trips.*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 departure from DCA to MDW with Delta Air Lines, filter your search by "Early Morning" and "Morning." Booking an early flight usually means cancellations are less likely.**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 makes traveling from DCA to MDW enjoyable with a rewarding loyalty program and an excellent in-flight experience. You even have the chance to collect points with Delta SkyMiles. Remember to sign up to Expedia's 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.