Cheap flights from Chicago to Massachusetts from $108

In general, January is the cheapest month to fly from Chicago to Massachusetts. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $201. If you aren’t able to travel to Massachusetts during the month of January, then flying in February is also cheap. Prices for this month can be found on momondo for an average of $231.

According to our data, Saturday is the cheapest day to fly to Massachusetts from Chicago. The lowest ticket price found for a Saturday departure recently was $270. 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 Chicago because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $346.

Our data shows that the cheapest Chicago to Massachusetts flights are usually those with departure times in the evening. Our users have found flights to Massachusetts in the evening for as low as $261. If you have a flexible travel schedule, then try to avoid flying in the afternoon when prices are $333 on average. Flights to Massachusetts from Chicago in the afternoon are generally more expensive because this time of day is more convenient for travelers’ schedules.

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

You are more likely to see cheaper flights to Massachusetts from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Massachusetts for around $277 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Massachusetts from Chicago for as low as $233 on momondo.

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

United Airlines, Southwest, and Delta are the most popular carriers operating from Chicago to Massachusetts

United Airlines, American Airlines and Delta are the top three most popular airlines that fly to Massachusetts from Chicago according to our data. United Airlines is the first choice among our users, with 44% of people opting to fly with this airline when traveling to Massachusetts. Keep in mind that there are 5 different airlines that fly to Massachusetts on a routine basis, so you have a few additional options to choose from.

As of October 2026, there are 28 flights per day flying from Chicago to Massachusetts. The most common time of day flights depart is 3:00PM, with 46% of flights taking off at noon.

198 flights are operational weekly from Chicago to Massachusetts as of October 2026. The most popular departure day for this route is Thu, with 36% of flights per week taking off on this day.