BOS to CHI, Logan International Airport to Cheap Flights

Based on HopeGoo data, Delta Air Lines offers one-way fares as low as US$54 on Cheapest nonstop routes (e.g. BOS to ORD on Tue, Mar 17), while American Airlines offers Cheapest nonstop round-trips from US$88 departing on Tue, Mar 10 and returning on Tue, Mar 17.

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

It takes about 3 hours 6 minutes to fly from Boston to Chicago.

By analyzing data from all airlines on the HopeGoo flight calendar, it looks like the best time to book a flight from Boston to Chicago 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 82 flight per week flying from Boston to Chicago. You can check the weekly schedule for popular airlines on this route below: United Airlines: S/M/T/W/T/F/S -- UA1349 (10:01)

To find best deals on flights from Boston to Chicago, 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 Tue, Mar 17, 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 Delta Air Lines. · 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 Chicago travel is around July. · Get exclusive promo codes for HopeGoo app users.

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

After crunching the numbers on our February flight calendar, it's currently cheapest to fly from Boston to Chicago on February 18, 2026 with American Airlines, with prices starting at US$47.

You can land at any one of the following hubs in Chicago, with Logan International Airport to O'Hare International Airport (BOS-ORD) is by far the most common option on this route: Midway International Airport (MDW) O'Hare International Airport (ORD) Chicago Rockford International Airport (RFD).

The time difference between Chicago and Boston 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.