Cheap flights from Boston to Chicago from R1 806

The month of January is, on average, the cheapest month to fly to Chicago from Boston, with most prices found around R3 234. If you are unable to visit Chicago during the month of January, then departing from Boston during the month February is also very affordable. Most momondo users find prices during this month for around R3 562.

On average, the least expensive day to fly to Chicago from Boston is on a Tuesday. momondo users have found tickets for Tuesday departures for as low as R2 464. However, this price may fluctuate depending on the airline, the season, and holidays. Be sure to avoid booking your departure on a Saturday as prices are generally higher than usual. According to our data, the average ticket price to Chicago on Saturday is R27 350.

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 R4 378 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 R3 694 on momondo.

There is only 1 cabin class 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.

As of September 2026, prices for Boston to Chicago flights are approximately 116% more expensive 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 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.

The number of flights available between Boston and Chicago is 47 per day as of September 2026. The most frequent departure time is 7:00, with 47% of daily flights leaving in the afternoon.

The number of flights available between Boston and Chicago is 335 per week as of September 2026. The most frequent departure day is Mon, with 21% of weekly flights leaving on this day.