Cheap flights from Illinois to Boston from $68

In general, January is the cheapest month to fly from Illinois to Boston. 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 during the month of January, then book flights to Boston from Illinois during September instead. Flights to Boston in September, while not as cheap as those in January, still average around $207.

The cheapest day to depart from Illinois to Boston is on a Wednesday when prices can be found for as low as $236. Be sure to avoid booking your departure on a Monday as prices are generally higher than usual. According to our data, the average ticket price to Boston on Monday is $292.

According to our data, the cheapest time of day to fly to Boston is in the evening. momondo users have found flights departing from Illinois to Boston in the evening for as low as $214. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. At noon is when there is more demand to fly to Boston, so prices are often more expensive at around $289 per ticket.

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

You are more likely to see cheaper flights to Boston from Illinois when booking weeks ahead of your departure date. In general, you can expect to find flights to Boston for around $229 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Boston from Illinois for as low as $184 on momondo.

There are 4 cabin classes available to choose from on Illinois to Boston Logan Intl 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 Southwest are the most popular carriers operating from Illinois to Boston Logan Intl

American Airlines, United Airlines and Delta are the top three most popular airlines that fly to Boston from Illinois according to our data. American Airlines is the first choice among our users, with 41% of people opting to fly with this airline when traveling to Boston. Keep in mind that there are 6 different airlines that fly to Boston on a routine basis, so you have a few additional options to choose from.

The number of flights available between Illinois and Boston is 21 per day as of February 2026. The most frequent departure time is 7:00AM, with 47% of daily flights leaving at noon.

As of February 2026, 147 flights take off from Illinois and land in Boston each week. The most common flight departure day for this route is Wed, with 43% of weekly flights taking off on this day.