Cheap flights from Boston to Chicago from $65

The month of September is, on average, the cheapest month to fly to Chicago from Boston, with most prices found around $187. If you’re not able to fly to Chicago in September, then January is your next best option. Flight prices from Boston to Chicago during January average around $200.

The cheapest day to depart on your flight to Chicago is on a Wednesday when prices can be found for as low as $308. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Boston to Chicago for around $404.

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Boston to Chicago during this time can be as low as $272. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $366.

Fly from Boston Logan Intl to Chicago Midway 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 $246 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Boston for as low as $222 on momondo.

There are 4 cabin classes available to choose from on Boston Logan Intl to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

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

American Airlines, United Airlines and Delta are the top three most popular airlines that fly to Chicago from Boston according to our data. American Airlines is the first choice among our users, with 43% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 6 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

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 169 minutes.

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

According to our data, United Airlines have had the least number of delays on this route over the last 12 months; with about 11% of their flights experiencing any sort of delay.

44 flights are operational daily from Boston to Chicago as of March 2026. The most popular departure time for this route is 7:00AM, with 51% of flights per day taking off at noon.

As of March 2026, 311 flights take off from Boston and land in Chicago each week. The most common flight departure day for this route is Mon, with 21% of weekly flights taking off on this day.