Cheap flights from Chicago Midway Airport to Boston from $84

In general, July is the cheapest month to fly from Chicago Midway Airport to Boston. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $247. If you aren’t able to travel during the month of July, then book flights to Boston from Chicago Midway Airport during June instead. Flights to Boston in June, while not as cheap as those in July, still average around $254.

The cheapest day to depart from Chicago Midway Airport to Boston is on a Wednesday when prices can be found for as low as $234. 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 $301.

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 Midway Airport 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. In the afternoon is when there is more demand to fly to Boston, so prices are often more expensive at around $288 per ticket.

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

You are more likely to see cheaper flights to Boston from Chicago Midway Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to Boston for around $292 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Boston from Chicago Midway Airport for as low as $210 on momondo.

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 128 minutes.

Generally, flights departing at night 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, Southwest have had the least number of delays on this route over the last 12 months; with about 26% of their flights experiencing any sort of delay.

As of May 2026, there are 3 flights per day flying from Chicago Midway Airport to Boston. The most common time of day flights depart is 7:00AM, with 47% of flights taking off at noon.

The number of flights available between Chicago Midway Airport and Boston is 24 per week as of May 2026. The most frequent departure day is Mon, with 21% of weekly flights leaving on this day.