Cheap flights from Chicago O'Hare Intl Airport to Massachusetts from $90

In general, January is the cheapest month to fly from Chicago O'Hare Intl Airport to Massachusetts. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $205. If you aren’t able to travel to Massachusetts during the month of January, then flying in November is also cheap. Prices for this month can be found on momondo for an average of $224.

According to our data, Saturday is the cheapest day to fly to Massachusetts from Chicago O'Hare Intl Airport. The lowest ticket price found for a Saturday departure recently was $247. 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 Chicago O'Hare Intl Airport because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $323.

Our data shows that the cheapest Chicago O'Hare Intl Airport 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 $233. If you have a flexible travel schedule, then try to avoid flying in the afternoon when prices are $306 on average. Flights to Massachusetts from Chicago O'Hare Intl Airport in the afternoon are generally more expensive because this time of day is more convenient for travelers’ schedules.

Fly from Chicago O'Hare Intl to Boston Logan Intl for the best Chicago O'Hare Intl - Massachusetts flight prices

You are more likely to see cheaper flights to Massachusetts from Chicago O'Hare Intl Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to Massachusetts for around $253 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Massachusetts from Chicago O'Hare Intl Airport for as low as $218 on momondo.

There are 4 cabin classes available to choose from on Chicago O'Hare Intl Airport 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, Delta, and JetBlue are the most popular carriers operating from Chicago O'Hare Intl to Massachusetts

United Airlines, American Airlines and Delta are the top three most popular airlines that fly to Massachusetts from Chicago O'Hare Intl Airport 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 4 different airlines that fly to Massachusetts on a routine basis, so you have a few additional options to choose from.

The number of flights available between Chicago O'Hare Intl Airport and Massachusetts is 80 per day as of August 2026. The most frequent departure time is 7:00AM, with 43% of daily flights leaving at noon.

As of August 2026, 564 flights take off from Chicago O'Hare Intl Airport and land in Massachusetts each week. The most common flight departure day for this route is Fri, with 20% of weekly flights taking off on this day.