Cheap flights from Chicago to Boston from $109

In general, January is the cheapest month to fly from Chicago to Boston. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $202. If you aren’t able to travel during the month of January, then book flights to Boston from Chicago during February instead. Flights to Boston in February, while not as cheap as those in January, still average around $232.

The cheapest day to depart from Chicago to Boston is on a Friday when prices can be found for as low as $278. 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 $349.

According to our data, the cheapest time of day to fly to Boston is in the evening. momondo users have found flights departing from Chicago to Boston in the evening for as low as $265. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. In the afternoon is when there is more demand to fly to Boston, so prices are often more expensive at around $334 per ticket.

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

You are more likely to see cheaper flights to Boston from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Boston for around $283 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Boston from Chicago for as low as $233 on momondo.

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

No. A direct flight is the cheapest option for a flight between Chicago to Boston.

As of November 2026, prices for Chicago to Boston flights are approximately 3% cheaper when compared to flights at the same time last year.

Frontier, JetBlue, and Delta are the most popular carriers operating from Chicago to Boston Logan Intl

United Airlines, American Airlines and Delta are the top three most popular airlines that fly to Boston from Chicago according to our data. United Airlines is the first choice among our users, with 43% of people opting to fly with this airline when traveling to Boston. Keep in mind that there are 5 different airlines that fly to Boston on a routine basis, so you have a few additional options to choose from.

Historically, on average around 26% of flights between Chicago and Boston have experienced a delay on any given week. The average delay length over the past 12 months has been 155 minutes.

Generally, flights departing in the morning tend to experience fewer delays. Flights in the early afternoon have, in the past, seen delays more frequently in comparison.

Saturday is statistically the day of the week which experiences the fewest number of delays on this flight route. Monday has historically seen more delays on average compared to the rest of the week.

According to our data, Delta have had the least number of delays on this route over the last 12 months; with about 22% of their flights experiencing any sort of delay.

As of November 2026, there are 50 flights per day flying from Chicago to Boston. The most common time of day flights depart is 1:00PM, with 46% of flights taking off in the afternoon.

As of November 2026, 355 flights take off from Chicago and land in Boston each week. The most common flight departure day for this route is Mon, with 19% of weekly flights taking off on this day.