Cheap flights from Boston to Chicago from $83

The month of September is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Boston averaging around $207.

The cheapest day to depart on your flight to Chicago O'Hare Intl Airport is on a Friday when prices can be found for as low as $313. This is often the case because there is less demand to fly during this day of the week. On the other hand, Sunday is the most expensive day to depart from Boston because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $409.

Flying to Chicago O'Hare Intl Airport from Boston in the evening is the least expensive time of day to depart. momondo users have found prices as low as $269 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $380. Of course, these prices can vary depending on the time of year and what airport you fly to.

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

You are more likely to see cheaper flights to Chicago O'Hare Intl Airport from Boston when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago O'Hare Intl Airport for around $249 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago O'Hare Intl Airport from Boston for as low as $220 on momondo.

United Airlines is the most popular carrier operating from Boston Logan Intl to Chicago O'Hare Intl

American Airlines, United Airlines and Delta are the top three most popular airlines that fly to Chicago O'Hare Intl Airport from Boston according to our data. American Airlines is the first choice among our users, with 45% of people opting to fly with this airline when traveling to Chicago O'Hare Intl Airport. Keep in mind that there are 6 different airlines that fly to Chicago O'Hare Intl Airport on a routine basis, so you have a few additional options to choose from.

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 in the evening have, in the past, seen delays more frequently in comparison.

Saturday is statistically the day of the week which experiences the fewest number of 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 least number of delays on this route over the last 12 months; with about 10% of their flights experiencing any sort of delay.

The number of flights available between Boston and Chicago O'Hare Intl Airport is 44 per day as of May 2026. The most frequent departure time is 3:00PM, with 48% of daily flights leaving in the afternoon.

As of May 2026, there are 312 flights per week flying from Boston to Chicago O'Hare Intl Airport. The most common day of the week flights depart is Thu, with 21% of flights taking off on this day.