Cheap Southwest Airlines flights New York (JFK) to Chicago (ORD)

You can discover cheap return Southwest Airlines flights from JFK to ORD by filtering your results from “Price (lowest to highest)” on Expedia. Or look for bargains 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.

Look for return or one-way flights to Chicago in January or February. You could find an affordable fare with Southwest Airlines during these off-peak travel months.

To find cheap Southwest Airlines fares from John F. Kennedy Intl. Airport (JFK) to O’Hare Intl. Airport (ORD), start searching one to three months before your intended departure. Securing 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 impact the price you pay. 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 journey 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.

Fill in your dates, hit search and select “Nonstop” on Expedia to browse any direct flights from JFK to ORD with Southwest Airlines or another airline.

Find Southwest Airlines’s earliest flights from JFK to ORD by selecting our “Morning” and “Early 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.

Hop on a Southwest Airlines flight from John F. Kennedy Intl. Airport (JFK) to Chicago, and you’ll probably land at O’Hare Intl. Airport (ORD). This is the airline’s primary hub in this city.

Changes are often free within 24 hours of making your booking, but your airline may charge a fee after that time. For more information about modifying your reservation, head to your “Trips,” select your flight and click on “Manage Booking.” If you want the freedom to update your itinerary without extra charges, apply the “Changes included” or “No cancel fee” filter when planning your next getaway.