$119 Cheap Delta flights Portland (PDX) to Chicago (MDW)

Finding cheap one-way Delta Air Lines flights from PDX to MDW from $119 on Expedia is easy — just filter by "Price (lowest to highest)." Alternatively, check out our budget-friendly return fares from $237 for your next exciting adventure.**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.

For cheap Delta Air Lines fares from Portland Intl. Airport (PDX) to Midway Intl. Airport (MDW), start searching one to three months before your intended departure. Securing domestic flights 34 to 86 days in advance could save you 25% compared to booking just 6 to 12 days ahead. The day you book can also impact the overall cost. Sunday is usually the most affordable, while Monday is often the most expensive for domestic flights. You can save 6% on average by booking on a Sunday.**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.

Browse Delta Air Lines's earliest flights from PDX to MDW by using our "Early Morning" and "Morning" filters. Not only will you arrive 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.

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