$74 Cheap American Airlines flights New York (LGA) to Chicago (ORD)

Make use of the "Price (lowest to highest)" filter on Expedia to find cheap American Airlines round-trip flights from $157 from LGA to ORD. Affordable one-way tickets from $74 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.

For cheap American Airlines fares from LaGuardia Airport (LGA) to O'Hare Intl. Airport (ORD), start searching one to three months before your intended departure. Reserving 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 most affordable, while Monday is often the most expensive for domestic flights. You can save 6% on average by booking your trip 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.

The first American Airlines flight from LGA to ORD takes off at 6:00AM UTC-5, landing at 7:50AM UTC-6. If you prefer to jet off later in the day, the last American Airlines flight leaves LGA at 8:00PM UTC-5 and lands at ORD at 9:56PM UTC-6. Flying early is often a smart choice as morning and mid-morning flights are 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.