Cheap flights from Chicago to Boston from £71

In general, November 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 £136. The month of October is another great option to travel to Boston, with average flight prices from Chicago averaging around £140.

The cheapest day to depart on your flight to Boston is on a Sunday when prices can be found for as low as £129. 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 Wednesday because tickets tend to average around £885. These prices are subject to change though, so be sure to set up a Price Alert for flights to Boston.

Our most recent data shows that the best time of day to fly to Boston is in the evening. Flights from Chicago to Boston during this time can be as low as £125. In the afternoon is when there is more demand to fly to Boston, so prices are often more expensive at around £709 per ticket.

Fly from Chicago Midway to Boston Logan Intl for the best Chicago - Boston Logan Intl flight prices

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 £180 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 £158 on momondo.

There are 3 cabin classes available to choose from on Chicago to Boston 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 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 148 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. Friday has historically seen more delays on average compared to the rest of the week.

According to our data, JetBlue 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 June 2026, 59 flights take off from Chicago and land in Boston each day. The most common flight departure time for this route is 19:00, with 38% of daily flights taking off at midday.

417 flights are operational weekly from Chicago to Boston as of June 2026. The most popular departure day for this route is Thu, with 19% of flights per week taking off on this day.