Cheap flights from Illinois to Massachusetts from $78

In general, January is the cheapest month to fly from Illinois to Massachusetts. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $190. If you aren’t able to travel to Massachusetts during the month of January, then flying in September is also cheap. Prices for this month can be found on momondo for an average of $207.

According to our data, Wednesday is the cheapest day to fly to Massachusetts from Illinois. The lowest ticket price found for a Wednesday departure recently was $234. 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, Monday is the most expensive day to depart from Illinois because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $296.

Our data shows that the cheapest Illinois 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 $211. If you have a flexible travel schedule, then try to avoid flying in the afternoon when prices are $287 on average. Flights to Massachusetts from Illinois 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 Illinois - Massachusetts flight prices

You are more likely to see cheaper flights to Massachusetts from Illinois when booking weeks ahead of your departure date. In general, you can expect to find flights to Massachusetts for around $231 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Massachusetts from Illinois for as low as $193 on momondo.

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

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

American Airlines, United Airlines and Delta are the top three most popular airlines that fly to Massachusetts from Illinois according to our data. American Airlines is the first choice among our users, with 38% of people opting to fly with this airline when traveling to Massachusetts. Keep in mind that there are 6 different airlines that fly to Massachusetts on a routine basis, so you have a few additional options to choose from.

As of April 2026, 109 flights take off from Illinois and land in Massachusetts each day. The most common flight departure time for this route is 11:00AM, with 49% of daily flights taking off at noon.

As of April 2026, there are 766 flights per week flying from Illinois to Massachusetts. The most common day of the week flights depart is Fri, with 17% of flights taking off on this day.