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

Use the "Price (lowest to highest)" filter on Expedia to look for cheap Southwest Airlines return flights from $214 from HOU to ORD. Affordable one-way options from $109 are also available.**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 affordable Southwest Airlines flights from William P. Hobby Airport (HOU) to O'Hare Intl. Airport (ORD) one to three months before your departure day. 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. No matter the fare class and itinerary, the best day to book a domestic flight is usually Sunday and the most expensive tends to be Monday. Passengers who book on a Sunday can save 6% on average compared to those who book their travel 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.

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