$59 Cheap United flights Detroit (DTW) to Chicago (ORD)

Set the "Price (lowest to highest)" filter on Expedia to find cheap United Airlines return flights from $128 from DTW to ORD. Affordable one-way fares from $59 are also on offer.**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 cheap United Airlines flights from Detroit Metropolitan Wayne County Airport (DTW) to O'Hare Intl. Airport (ORD) one to three months before your 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 class and itinerary, the best day of the week to book a domestic flight is generally Sunday and the most expensive is typically Monday. Passengers who book on a Sunday can save 6% on average compared to those who book 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.

The earliest United Airlines flight from DTW to ORD departs at 6:00AM UTC-5, touching down at 6:40AM UTC-6. If you prefer to jet off later in the day, the last United Airlines flight leaves DTW at 6:12PM UTC-5 and touches down at ORD at 6:41PM UTC-6. Flying before noon is generally a wise choice as morning flights are least likely to face 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.

Depart from DTW to ORD with United Airlines and enjoy a host of benefits including a rewarding loyalty program. When you book through Expedia as a United Mileage Plus and One Key™ member, you could also earn OneKeyCash™* to spend on select future travel purchases.*OneKeyCash™ disclaimer - OneKeyCash™ is not redeemable for cash and can only be used on Expedia, Hotels.com and Vrbo.