$59 Cheap United flights Boston (BOS) to Chicago (ORD)

Use the “Price (lowest to highest)” filter on Expedia to find cheap United Airlines return flights from $117 from BOS to ORD. Affordable one-way options 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 fly to Chicago with United Airlines. You could also find fantastic deals on return and one-way tickets in February.

For cheap United Airlines fares from Logan Intl. Airport (BOS) 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 how much you pay. Sunday is usually the cheapest, 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.

United Airlines operates direct flights from Logan Intl. Airport (BOS) to O’Hare Intl. Airport (ORD), with 38 weekly departures. Simply apply the “Nonstop” and “Airline” filters during your search on Expedia to see all direct United Airlines flights to ORD.

It takes approximately 2h 59m to fly nonstop from Logan Intl. Airport (BOS) to O’Hare Intl. Airport (ORD) with United Airlines.

Thursday has the most United 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 find something that will suit your schedule.

The earliest United Airlines flight from BOS to ORD departs at 6:00AM UTC-5, arriving at 8:03AM UTC-6. If you’d like to head off later in the day, the last United Airlines flight leaves BOS at 6:25PM UTC-5 and touches down at ORD at 8:25PM UTC-6. Flying before noon is generally a good idea as morning flights tend to experience fewer cancellations.**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.

United Airlines flights from Logan Intl. Airport (BOS) to Chicago come in to land at O’Hare Intl. Airport (ORD) and Midway Intl. Airport (MDW). The primary Chicago hub serviced by this airline is ORD. It’s worth considering flights landing at nearby airports on Expedia as you may find lower fares.

A rewarding loyalty program and the chance to rack up points through United Mileage Plus are the start of the reasons to depart from BOS to ORD with United Airlines. Plus, when you sign up to our One Key™ program, you can earn OneKeyCash™* on top of any airline loyalty program earnings. You can put it toward your future trips.*OneKeyCash™ disclaimer - OneKeyCash™ is not redeemable for cash and can only be used on Expedia, Hotels.com and Vrbo.

For the Logan Intl. Airport (BOS) to O’Hare Intl. Airport (ORD) route, United Airlines typically operates Boeing 737-800 and Boeing 737 MAX 8 planes. Don’t forget that last-minute changes are possible for operational reasons, meaning your flight could be on a different aircraft.

Changes are typically free within 24 hours of making a booking, but your airline may add a charge after that time. For further details about modifying your reservation, head to your “Trips,” select your flight and click on “Manage Booking.” If you want the flexibility to adjust your plans without extra charges, tick the “No cancel fee” or “Changes included” filter when organizing your trip.