CHI to BOS, to Logan International Airport Cheap Flights

Based on HopeGoo data, United Airlines offers one-way fares as low as US$54 on Cheapest nonstop routes (e.g. ORD to BOS on Sun, Apr 5), while Delta Air Lines offers Cheapest nonstop round-trips from US$93 departing on Sat, Feb 28 and returning on Sat, Feb 28.

At the moment, you can catch a nonstop flight from Chicago to Boston with the following airlines, including: Delta Air Lines American Airlines United Airlines Selected airlines are based on historical data collected from flight bookings users made on HopeGoo within the last 90 days.

It takes about 2 hours 27 minutes to fly from Chicago to Boston.

By analyzing data from all airlines on the HopeGoo flight calendar, it looks like the best time to book a flight from Chicago to Boston is around 40 days (6 weeks) in advance, and the best time to fly is usually on Tuesday, Wednesday, and Saturday. Tuesday typically offers the cheapest flights for departure, while Saturday offers the best return deals.

Based on HopeGoo data in the past 4 weeks, there is 81 flight per week flying from Chicago to Boston. You can check the weekly schedule for popular airlines on this route below: American Airlines: S/M/T/W/T/F/S -- AA3710 (07:11) Delta Air Lines: S/M/T/W/T/F/S -- DL5633 (07:26)

To find best deals on flights from Chicago to Boston, you can use various tools on HopeGoo: · Be flexible with your travel dates to get the cheapest flight deal. Now the cheapest flight deal is on Sun, Apr 5, with one-way flights priced at just US$54. · Compare airlines strategically. Budget carriers often provide the lowest base fares, while we found the most affordable airline currently operating on this route is United Airlines. · Set up price alerts to easily monitor ticket prices without having to check every day. · Check HopeGoo flight deals and promo codes frequently. · Avoid peak season unless you book very early. It seems the peak season for Boston travel is around July. · Get exclusive promo codes for HopeGoo app users.

The cheapest months to fly from Chicago to Boston is October, when demand for travel is lower.

After crunching the numbers on our February flight calendar, it's currently cheapest to fly from Chicago to Boston on February 19, 2026 with Jetblue Airways, with prices starting at US$41.

You can land at any one of the following hubs in Boston, with O'Hare International Airport to Logan International Airport (ORD-BOS) is by far the most common option on this route: Hartford Barnes Airport (BNH) Logan International Airport (BOS) Portsmouth International Airport at Pease (PSM).

The time difference between Boston and Chicago is 1h.

Tickets can only be changed or canceled if permitted by airline policy. To submit a change or cancellation request, go to the flight bookings page, select the option to change or cancel your HopeGoo, choose the relevant passengers and segment, and submit a request. Please note that additional charges may apply according to the airline ticket policy. However, if the flight has been rescheduled and you would like to change or cancel your ticket, you can submit an involuntary cancellation request. For more details about change and cancellation policies, please check the customer support pages.