$104 Find Cheap Flights from Chicago Midway Airport to Boston - Compare and Save

If your flying dates are flexible, you should consider flying to Boston on a Friday, as we generally find the cheapest rates on that day for this route. On the other hand, Sunday is the most expensive day to fly from Chicago Midway Airport to Boston. For your return ticket, we recommend flying on a Thursday and avoiding Sundays for the best deals.

The cheapest month for flights from Chicago Midway Airport to Boston is September, where tickets cost $257 (return) on average. On the other hand, the most expensive months are January and June, where the average cost of round-trip tickets is $414 and $335 respectively.

Weekly flights between Chicago and Boston historically see delays in approximately 26% of cases, with the average delay over the past year being 127 minutes.

Typically, flights leaving at night tend to face fewer delays, whereas flights in the early afternoon have historically encountered delays more often.

Statistically, Saturday is the day of the week with the fewest delays on this flight route, while Monday has typically experienced more delays than other days.

Based on our data, Southwest have experienced the fewest delays on this route in the past 12 months, with only about 26% of their flights encountering any delays.

There is only one cabin class option available for the route, which is Economy. Perform a search on KAYAK to find the latest prices and availability for all cabin fares, which differ across airlines.

Each day, there are between 4 and 5 nonstop flights that take off from Chicago Midway Airport and land in Boston, with an average flight time of 2h 19m. The most common departure time is 12:00 pm and most flights take off in the morning. Each week, there are 34 flights. The most frequent day of departure is Monday, when 15% of all weekly flights depart. The fewest flights depart on a Saturday.