Cheap flights from Chicago to Boston from $81

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 $182. If you aren’t able to travel during the month of November, then book flights to Boston from Chicago during October instead. Flights to Boston in October, while not as cheap as those in November, still average around $186.

The cheapest day to depart from Chicago to Boston is on a Wednesday when prices can be found for as low as $233. Be sure to avoid booking your departure on a Monday as prices are generally higher than usual. According to our data, the average ticket price to Boston on Monday is $299.

According to our data, the cheapest time of day to fly to Boston is in the evening. momondo users have found flights departing from Chicago to Boston in the evening for as low as $212. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. In the afternoon is when there is more demand to fly to Boston, so prices are often more expensive at around $285 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 $233 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Boston from Chicago for as low as $198 on momondo.

Southwest, United Airlines, and JetBlue are the most popular carriers operating from Chicago to Boston Logan Intl

American Airlines, United Airlines and Delta are the top three most popular airlines that fly to Boston from Chicago according to our data. American Airlines is the first choice among our users, with 39% of people opting to fly with this airline when traveling to Boston. Keep in mind that there are 6 different airlines that fly to Boston on a routine basis, so you have a few additional options to choose from.

Historically, on average around 25% 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 147 minutes.

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

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

As of April 2026, there are 41 flights per day flying from Chicago to Boston. The most common time of day flights depart is 6:00AM, with 51% of flights taking off at noon.

As of April 2026, 293 flights take off from Chicago and land in Boston each week. The most common flight departure day for this route is Thu, with 25% of weekly flights taking off on this day.