Cheap flights from Boston to Chicago from ₹ 10,556

The cheapest month to fly to Chicago O'Hare Intl Airport from Boston is in January. Flight prices, which tend to average around ₹ 18,904, are often lower during this time because this is during the off-season. If you don’t want to visit Chicago O'Hare Intl Airport in January, then you should wait until February to fly from Boston, when ticket prices are also cheap, with an average price of ₹ 22,647.

The cheapest day to depart on your flight to Chicago O'Hare Intl Airport is on a Saturday when prices can be found for as low as ₹ 15,062. This is often the case because there is less demand to fly during this day of the week. If your travel schedule is flexible, try to avoid departing on a Monday because tickets tend to average around ₹ 122,036. These prices are subject to change though, so be sure to set up a Price Alert for flights to Chicago O'Hare Intl Airport.

In the afternoon is the cheapest time of day to fly from Boston to Chicago O'Hare Intl Airport when you can find flight prices for as low as ₹ 24,741. Flying to Chicago O'Hare Intl Airport in the afternoon is an ideal time because this is during off-peak travel hours. If you have a flexible travel schedule, then try to avoid flying in the morning when prices are ₹ 36,192 on average. Flights to Chicago O'Hare Intl Airport from Boston in the morning are generally more expensive because this time of day is more convenient for travellers’ schedules.

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 ₹ 25,758 when searching weeks before you fly. 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 ₹ 21,591 on momondo.

There are 2 cabin classes available to choose from on Boston to Chicago O'Hare Intl Airport flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

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 at night tend to experience fewer delays. Flights departing in the evening have, in the past, seen delays more frequently in comparison.

Wednesday is statistically the day of the week that experiences the fewest delays on this flight route. Monday 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 9% of their flights experiencing any sort of delay.

As of October 2026, there are 41 flights per day flying from Boston to Chicago O'Hare Intl Airport. The most common time of day flights depart is 07:00, with 41% of flights taking off in the afternoon.

289 flights are operational weekly from Boston to Chicago O'Hare Intl Airport as of October 2026. The most popular departure day for this route is Sun, with 24% of flights per week taking off on this day.