$69 Cheap American Airlines flights Boston (BOS) to Chicago (ORD)

Finding cheap one-way American Airlines flights from BOS to ORD from $69 on Expedia couldn’t be easier — just filter by “Price (lowest to highest).” Alternatively, check out our budget-friendly round-trip fares from $132 for your next exciting vacation.**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.

American Airlines flights to Chicago are often more affordable in the low-season months of January and February. Whether you’re after a return or one-way ticket, you could score a better deal then.

Begin your search one to three months ahead of your departure date to score cheaper fares on American Airlines flights from Logan Intl. Airport (BOS) 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 reduce costs by buying your fare on a Sunday, as it’s 6% cheaper on average than a Monday, the most expensive day to book.* Nail your timing, 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.

Easily travel from Logan Intl. Airport (BOS) to O’Hare Intl. Airport (ORD) on any of American Airlines’s 41 weekly direct flights. Make use of our “Nonstop” and “Airline” filters to find the American Airlines flight that’ll get you to ORD at a time that suits you.

The journey time for a direct American Airlines flight from Logan Intl. Airport (BOS) to O’Hare Intl. Airport (ORD) takes approximately 3h 4m.

Wednesday has the most American Airlines flights from Logan Intl. Airport (BOS) to O’Hare Intl. Airport (ORD). With 6 daily departures, this is the best day of the week to book something that will suit your schedule.

The first flight from BOS to ORD with American Airlines departs at 6:00AM UTC-5. You’ll land at 8:08AM UTC-6. The final American Airlines flight of the day takes off at 7:47PM UTC-5 and arrives at 9:56PM UTC-6. With 20% fewer cancellations for morning departures, setting off early is generally the best choice.**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.

Most American Airlines flights from Logan Intl. Airport (BOS) to Chicago land at O’Hare Intl. Airport (ORD). This is the airline’s primary gateway to this city. It’s worth exploring Expedia for flights to nearby airports like Midway Intl. Airport (MDW), as prices may be lower.

You’ll likely board a Boeing 737-800 or an Embraer 175 when flying American Airlines from Logan Intl. Airport (BOS) to O’Hare Intl. Airport (ORD). However, keep in mind that a different aircraft could be assigned to your route due to operational demands.

You can usually cancel or reschedule your flight, although there may be additional fees if your booking was made more than 24 hours ago. Prefer to keep your options open? Make use of Expedia’s “No cancel fee” and “Changes included” filters to find flights that won’t charge extra if you need to alter your plans. To make changes, head to “Trips,” select your flight and click on “Manage Booking” for more information.