$59 Cheap Southwest Airlines flights Chicago (ORD) to St. Louis (STL)

Set the “Price (lowest to highest)” filter on Expedia to look for cheap Southwest Airlines return flights from $107 from ORD to STL. Affordable one-way tickets from $59 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.

Southwest Airlines flights to St. Louis tend to be cheaper in the low-season months of January and February. Whether you’re searching for a one-way or round-trip ticket, you could land a better deal then.

Begin your search one to three months before your departure to get cheap fares on Southwest Airlines flights from O’Hare Intl. Airport (ORD) to Lambert-St. Louis Intl. Airport (STL). 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.* Time it well, 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.

Enter your dates, hit search and select the “Nonstop” filter on Expedia to browse any direct flights from ORD to STL with Southwest Airlines or another carrier.

Filter your results by “Morning” and “Early Morning” to find the earliest departures from ORD to STL. Heading off early means flight cancellations are less likely.**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.

Southwest Airlines flights from O’Hare Intl. Airport (ORD) to St. Louis come in to land at Lambert-St. Louis Intl. Airport (STL). This is the main gateway to this destination.

Changes are usually free within 24 hours of making a booking, but your airline may charge you after that time. For further information about modifying your reservation, head to your “Trips,” select your flight and click on “Manage Booking.” If you want the freedom to adjust your plans without being charged, apply the “No cancel fee” or “Changes included” filter when organizing your next break.