$59 Cheap American Airlines flights Chicago (ORD) to Boston (BOS)

Apply the “Price (lowest to highest)” filter on Expedia to look for cheap American Airlines return flights from $108 from ORD to BOS. Affordable one-way tickets from $59 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.

January is one of the most affordable months to jet off to Boston with American Airlines. You could also find excellent prices on one-way and round-trip tickets in February.

For cheap American Airlines fares from O’Hare Intl. Airport (ORD) to Logan Intl. Airport (BOS), start searching one to three months before your planned 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 generally the most affordable, while Monday is often the most expensive for domestic flights. You can save 6% on average by booking your flight 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.

American Airlines operates direct flights from O’Hare Intl. Airport (ORD) to Logan Intl. Airport (BOS), with 41 weekly departures. Simply select the “Nonstop” and “Airline” filters while searching on Expedia to find all direct American Airlines flights to BOS.

From takeoff till touchdown, a direct American Airlines flight from O’Hare Intl. Airport (ORD) to Logan Intl. Airport (BOS) typically takes 2h 25m.

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

The earliest flight from ORD to BOS with American Airlines departs at 6:00AM UTC-6. You’ll touch down at 9:33AM UTC-5. The final American Airlines flight of the day leaves at 8:20PM UTC-6 and arrives at 11:44PM UTC-5. With approximately 20% fewer cancellations for early and mid-morning flights, setting off early is usually the smartest 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.

Logan Intl. Airport (BOS) is the main hub for American Airlines flights from O’Hare Intl. Airport (ORD) to Boston. But the airline also travels to T.F. Green Airport (PVD). Make sure you select the “All Airports” option for your destination to see what’s available for your visit to Boston.

American Airlines typically flies Boeing 737-800 planes for flights from O’Hare Intl. Airport (ORD) to Logan Intl. Airport (BOS). This airline also operates the Embraer 175 on this route. Keep in mind that aircraft type can vary due to operational reasons, so the plane you catch might be different on the day you travel.

Depending on your ticket type, a fee will generally apply if you cancel or reschedule your booking more than 24 hours after it has been confirmed. To secure flexible fares, select our “Changes included” and “No cancel fee” boxes while looking for flights. To learn more about modifying or canceling your reservation, head to “Trips,” select your flight and click on “Manage Booking.”