$109 Cheap Southwest Airlines flights Chicago (ORD) to Houston (HOU)

You can find cheap round-trip Southwest Airlines flights from $217 from ORD to HOU by organizing your results from "Price (lowest to highest)" on Expedia. Or look for bargains from $109 for a one-way journey.**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.

Begin your search one to three months before your departure to get cheaper fares on Southwest Airlines flights from O'Hare Intl. Airport (ORD) to William P. Hobby Airport (HOU). You can save 25% by booking your domestic flight 34 to 86 days in advance versus last-minute reservations made 6 to 12 days out. You could also cut 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 journeys.*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.

Search Southwest Airlines's earliest flights from ORD to HOU by using our "Early Morning" and "Morning" filters. Not only will you arrive at your destination 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.