$95 Cheap Southwest Airlines flights New York (LGA) to Chicago (ORD)

Make use of the "Price (lowest to highest)" filter on Expedia to find cheap Southwest Airlines round-trip flights from $189 from LGA to ORD. Affordable one-way fares from $95 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.

Begin your search one to three months before your departure to get cheap fares on Southwest Airlines flights from LaGuardia Airport (LGA) to O'Hare Intl. Airport (ORD). 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 flights.*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.

Filter your results by "Early Morning" and "Morning" to see the earliest departures from LGA to ORD. Heading off early means you're less likely to experience 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.