Cheap flights from Boston to Chicago from £58

The cheapest month to fly to Chicago from Boston is in September. Flight prices, which tend to average around £123, are often lower during this time because this is during the off-season. If you aren’t able to travel during the month of September, then book flights to Chicago from Boston during February instead. Flights to Chicago in February, while not as cheap as those in September, still average around £150.

The cheapest day to depart on your flight to Chicago is on a Sunday when prices can be found for as low as £182. This is often the case because there is less demand to fly during this day of the week. The most expensive day to fly to Chicago is Tuesday, with ticket prices averaging around £717.

Flying to Chicago from Boston in the morning is the least expensive time of day to depart. momondo users have found prices as low as £204 when looking at flights departing in the morning. Flights in the afternoon are often more expensive, with an average ticket price of £289.

Fly from Boston Logan Intl to Chicago O'Hare Intl for the best Boston Logan Intl - Chicago flight prices

You are more likely to see cheaper flights to Chicago from Boston when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around £183 when searching weeks before you fly. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Boston for as low as £162 on momondo.

There are 3 cabin classes available to choose from on Boston to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

You could potentially save up to 14% on your flight if you consider stops on a Boston to Chicago flight.

As of April 2026, prices for Boston to Chicago flights are approximately 18% cheaper when compared to flights at the same time last year.

Historically, on average around 15% of flights between Boston and Chicago have experienced a delay on any given week. The average delay length over the past 12 months has been 172 minutes.

Generally, flights departing in the morning tend to experience fewer delays. Flights departing in the evening have, in the past, seen delays more frequently in comparison.

Saturday is statistically the day of the week that experiences the fewest delays on this flight route. Sunday has historically seen more delays on average compared to the rest of the week.

According to our data, United Airlines have had the fewest delays on this route over the last 12 months, with about 10% of their flights experiencing any sort of delay.

44 flights are operational daily from Boston to Chicago as of April 2026. The most popular departure time for this route is 16:00, with 42% of flights per day taking off in the afternoon.

The number of flights available between Boston and Chicago is 312 per week as of April 2026. The most frequent departure day is Mon, with 21% of weekly flights leaving on this day.