£80 Find Cheap Flights from Chicago to Boston – Compare and Save

For Chicago to Boston, Sunday is the cheapest day to fly on average and Wednesday is the most expensive. Flying from Boston back to Chicago, the best deals are generally found on Sunday, with Monday being the most expensive.

The cheapest month for flights from Chicago O'Hare Intl Airport to Boston is January, where tickets cost £150 (return) on average. On the other hand, the most expensive months are August and June, where the average cost of round-trip tickets is £216 and £213 respectively.

In the past 5 days, the cheapest return tickets from Chicago to Boston were found on Frontier (£138) and Delta (£159).

Chicago and Boston are connected by different airlines. The airlines that fly that route the most regularly are American Airlines (70 flights per week), United Airlines (68 flights per week), and Delta (26 flights per week).

Weekly flights between Chicago and Boston historically see delays in approximately 25% of cases, with the average delay over the past year being 154 minutes.

Typically, flights leaving in the morning 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 Sunday has typically experienced more delays than other days.

Based on our data, Delta have experienced the fewest delays on this route in the past 12 months, with only about 20% of their flights encountering any delays.

There are 2 cabin class options for the route. These are Business and 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 23 and 26 direct flights that take off from Chicago O'Hare Intl Airport and land in Boston, with an average flight time of 2h 37m. The most common departure time is 06:00 and most flights take off in the morning. Each week, there are 177 flights. The most frequent day of departure is Monday, when 15% of all weekly flights depart. The fewest flights depart on a Sunday.