Cheap flights from Massachusetts to Chicago from $100

The month of February is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Massachusetts averaging around $236.

The cheapest day to depart on your flight to Chicago O'Hare Intl Airport is on a Friday when prices can be found for as low as $318. This is often the case because there is less demand to fly during this day of the week. On the other hand, Sunday is the most expensive day to depart from Massachusetts because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $416.

Flying to Chicago O'Hare Intl Airport from Massachusetts in the evening is the least expensive time of day to depart. momondo users have found prices as low as $283 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $386. 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 O'Hare Intl for the best Massachusetts - Chicago O'Hare Intl flight prices

You are more likely to see cheaper flights to Chicago O'Hare Intl Airport from Massachusetts when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago O'Hare Intl Airport for around $265 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago O'Hare Intl Airport from Massachusetts for as low as $225 on momondo.

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

Delta, United Airlines, and American Airlines are the most popular carriers operating from Massachusetts to Chicago O'Hare Intl

United Airlines, American Airlines and Delta are the top three most popular airlines that fly to Chicago O'Hare Intl Airport from Massachusetts according to our data. United Airlines is the first choice among our users, with 39% of people opting to fly with this airline when traveling to Chicago O'Hare Intl Airport. Keep in mind that there are 4 different airlines that fly to Chicago O'Hare Intl Airport on a routine basis, so you have a few additional options to choose from.

As of September 2026, there are 72 flights per day flying from Massachusetts to Chicago O'Hare Intl Airport. The most common time of day flights depart is 7:00AM, with 44% of flights taking off in the afternoon.

As of September 2026, 508 flights take off from Massachusetts and land in Chicago O'Hare Intl Airport each week. The most common flight departure day for this route is Fri, with 22% of weekly flights taking off on this day.