Cheap flights from Chicago Midway Airport to Boston from $111

In general, February 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 $277. If you aren’t able to travel during the month of February, then book flights to Boston from Chicago Midway Airport during November instead. Flights to Boston in November, while not as cheap as those in February, still average around $295.

The cheapest day to depart from Chicago Midway Airport to Boston is on a Saturday when prices can be found for as low as $265. 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 $338.

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 $256. 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 $321 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 $340 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 $246 on momondo.

There is only 1 cabin class available to choose from on Chicago Midway Airport to Boston flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Historically, on average around 27% 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 137 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 27% of their flights experiencing any sort of delay.

As of October 2026, there are 4 flights per day flying from Chicago Midway Airport to Boston. The most common time of day flights depart is 12:00PM, with 47% of flights taking off in the afternoon.

The number of flights available between Chicago Midway Airport and Boston is 31 per week as of October 2026. The most frequent departure day is Mon, with 23% of weekly flights leaving on this day.