Cheap flights from Boston to Chicago from $115

The month of December is, on average, the cheapest month to fly to Chicago Midway Airport from Boston, with most prices found around $134. If you are unable to visit Chicago Midway Airport during the month of December, then departing from Boston during the month January is also very affordable. Most momondo users find prices during this month for around $167.

According to our data, Thursday is the cheapest day to fly to Chicago Midway Airport from Boston. The lowest ticket price found for a Thursday departure recently was $359. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Sunday is the most expensive day to depart from Boston because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $455.

Flying to Chicago Midway Airport from Boston at noon is the least expensive time of day to depart. momondo users have found prices as low as $352 when looking at flights departing at noon. Try not to purchase tickets in the morning because they tend to be around $402. Of course, these prices can vary depending on the time of year and what airport you fly to.

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

You are more likely to see cheaper flights to Chicago Midway Airport from Boston when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago Midway Airport for around $288 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago Midway Airport from Boston for as low as $238 on momondo.

There is only 1 cabin class available to choose from on Boston to Chicago Midway Airport flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

You could potentially save up to 30% on your flight if you consider stops on a Boston to Chicago Midway Airport flight.

As of November 2026, prices for Boston to Chicago Midway Airport flights are approximately 98% more expensive when compared to flights at the same time last year.

Southwest is the most popular carrier operating from Boston Logan Intl to Chicago Midway

Southwest, JetBlue and Delta are the top three most popular airlines that fly to Chicago Midway Airport from Boston according to our data. Southwest is the first choice among our users, with 93% of people opting to fly with this airline when traveling to Chicago Midway Airport. Keep in mind that there are 4 different airlines that fly to Chicago Midway Airport on a routine basis, so you have a few additional options to choose from.

The number of flights available between Boston and Chicago Midway Airport is 2 per day as of November 2026. The most frequent departure time is 7:00AM, with 52% of daily flights leaving in the afternoon.

16 flights are operational weekly from Boston to Chicago Midway Airport as of November 2026. The most popular departure day for this route is Mon, with 25% of flights per week taking off on this day.