$150 Cheap American Airlines flights Hilton Head Island (HHH) to Chicago (ORD)

Grab affordable return American Airlines flights from $288 from HHH to ORD by filtering your results from “Price (lowest to highest)” on Expedia. Or search for deals from $150 for a one-way trip.**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 round-trip or one-way flights to Chicago in January or February. You could find an affordable fare with American Airlines during these off-peak months.

For cheap American Airlines fares from Hilton Head Island Airport (HHH) to O’Hare Intl. Airport (ORD), start searching one to three months before your planned 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 affect the overall price. Sunday is typically the cheapest, while Monday is often the most expensive for domestic flights. You can save 6% on average by choosing to book 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.

To figure out if there’s a direct trip from HHH to ORD with American Airlines or other carriers, check the “Nonstop” box when looking for tickets.

Sort your results by “Morning” and “Early Morning” to browse the earliest departures from HHH to ORD. Jetting 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.

Hop on an American Airlines flight from Hilton Head Island Airport (HHH) to Chicago, and you’re most likely to land at O’Hare Intl. Airport (ORD). This is the airline’s primary hub here.

It’s generally possible to change or cancel your flight, although additional fees may apply if your booking was made more than 24 hours ago. Need flexible options? Use our “Changes included” or “No cancel fee” filter to find flights that won’t charge extra if you have to alter your plans. To modify your booking, head to “Trips,” select your flight and click on “Manage Booking” for further information.