Cheap flights from Chicago to Boston from R1 807

In general, January is the cheapest month to fly from Chicago to Boston. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around R3 272. If you aren’t able to travel during the month of January, then book flights to Boston from Chicago during February instead. Flights to Boston in February, while not as cheap as those in January, still average around R3 760.

You are more likely to see cheaper flights to Boston from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Boston for around R4 323 when searching weeks before you fly. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Boston from Chicago for as low as R3 728 on momondo.

Historically, on average around 26% of flights between Chicago and Boston have experienced a delay on any given week. The average delay length over the past 12 months has been 153 minutes.

Generally, flights departing in the morning tend to experience fewer delays. Flights departing in the early afternoon 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. Monday has historically seen more delays on average compared to the rest of the week.

According to our data, Delta have had the fewest delays on this route over the last 12 months, with about 21% of their flights experiencing any sort of delay.

As of September 2026, 47 flights take off from Chicago and land in Boston each day. The most common flight departure time for this route is 9:00, with 45% of daily flights taking off at midday.

As of September 2026, 335 flights take off from Chicago and land in Boston each week. The most common flight departure day for this route is Fri, with 21% of weekly flights taking off on this day.