$68 Cheap United flights Chicago (ORD) to Boston (BOS)

Apply the “Price (lowest to highest)” filter on Expedia to search for cheap United Airlines return flights from $125 from ORD to BOS. Affordable one-way tickets from $68 are available too.**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 one-way or return flights to Boston in January or February. You could find an affordable fare with United Airlines during these off-peak times.

Look for affordable United Airlines flights from O’Hare Intl. Airport (ORD) to Logan Intl. Airport (BOS) one to three months before your departure. Travelers who book domestic flights 34 to 86 days in advance can save 25% compared to those who book just 6 to 12 days ahead. Regardless of fare class and itinerary, the best day to book a domestic flight is generally Sunday and the most expensive day is typically Monday. Passengers who book on a Sunday can save 6% on average compared to those who book their travel on a Monday.**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.

Take off on one of United Airlines’s 38 weekly direct flights from O’Hare Intl. Airport (ORD) to Logan Intl. Airport (BOS). To see your options, enter your dates, destination and origin and hit search. Then apply the “Nonstop” and “Airline” filters.

Leave O’Hare Intl. Airport (ORD) for Logan Intl. Airport (BOS) on a direct United Airlines flight, and you’ll be airborne for about 2h 26m.

Sunday has the most United Airlines flights from O’Hare Intl. Airport (ORD) to Logan Intl. Airport (BOS). With 6 daily departures, this is a great day to find something that will suit your schedule.

Departing ORD at 7:30AM UTC-6, the earliest United Airlines flight to BOS lands at 10:56AM UTC-5. Traveling earlier in the day means you’ll be less likely to encounter cancellations or delays.* Don’t like early starts? The last United Airlines flight from ORD to BOS departs at 6:30PM UTC-6 and touches down at 9:59PM UTC-5.*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 O’Hare Intl. Airport (ORD) to Boston arrive at Logan Intl. Airport (BOS) and T.F. Green Airport (PVD). The main Boston gateway served by this airline is BOS. It’s always worth exploring flights arriving at nearby airports on Expedia as they may have cheaper fares.

With a rewarding loyalty program, United Airlines is a popular choice for many passengers journeying from ORD to BOS. Plus, as a United Mileage Plus and One Key™ member booking through Expedia, you can earn OneKeyCash™* on eligible flights along with your airline miles.*OneKeyCash™ disclaimer - OneKeyCash™ is not redeemable for cash and can only be used on Expedia, Hotels.com and Vrbo.

For the O’Hare Intl. Airport (ORD) to Logan Intl. Airport (BOS) route, United Airlines typically uses Boeing 737 MAX 9 and Boeing 737-900 planes. Don’t forget that last-minute changes are possible for operational reasons, meaning your flight could be on another aircraft.

Depending on the type of ticket you purchased, a fee is typically charged if you modify or cancel your booking more than 24 hours after it has been confirmed. To secure plane tickets with more flexibility, select our “Changes included” or “No cancel fee” filter while searching for flights. For additional information on canceling or modifying your reservation, visit “Trips,” select your flight and click on “Manage Booking.”