$109 Cheap Delta flights Houston (HOU) to Chicago (MDW)

Apply the "Price (lowest to highest)" filter on Expedia to find cheap Delta Air Lines round-trip flights from $207 from HOU to MDW. Affordable one-way tickets from $109 are available as well.**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.

To find cheap Delta Air Lines fares from William P. Hobby Airport (HOU) to Midway Intl. Airport (MDW), start searching one to three months before your planned 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 affect the overall cost. Sunday is typically the cheapest, 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.

Find Delta Air Lines's earliest flights from HOU to MDW by selecting our "Morning" and "Early Morning" filters. Not only will you get to where you're going sooner, early departures also have a 20% less chance of being 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 traveling from HOU to MDW more enjoyable with a rewarding loyalty program and an excellent in-flight experience. You even have the chance to collect points with Delta SkyMiles. Be sure to join our 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.