£83 Find Cheap Flights from Boston to Chicago – Compare and Save

If you are looking for a flight deal from Boston to Chicago, look for departures on Thursdays and avoid leaving on a Wednesday, as it's usually the priciest day. When flying back from Chicago, Sunday is the cheapest day to fly and Wednesday is the most expensive.

The cheapest month for flights from Boston to Chicago O'Hare Intl Airport is January, where tickets cost £149 (return) on average. On the other hand, the most expensive months are September and October, where the average cost of round-trip tickets is £226 and £223 respectively.

Yes, flying with a stopover may cost you more time, but you can also save money on the route, with a 1 stop stopover the cheapest option at £122 on average.

To get a below average price on the flight from Boston to Chicago O'Hare Intl Airport, you should book around 3 weeks before departure, which saves you about 19% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 25 weeks before departure.

In the past 5 days, the cheapest return tickets from Boston to Chicago were found on JetBlue (£162) and United Airlines (£165).

American Airlines connects Boston to Chicago with 70 flights per week. United Airlines also offers 70 flights per week, while Delta follows with 27 flights per week.

Weekly flights between Boston and Chicago historically see delays in approximately 15% of cases, with the average delay over the past year being 172 minutes.

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

Statistically, Wednesday 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, United Airlines have experienced the fewest delays on this route in the past 12 months, with only about 9% of their flights encountering any delays.

There are 4 cabin class options for the route. These are First, Business, Economy and Prem 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 25 and 26 direct flights that take off from Boston and land in Chicago O'Hare Intl Airport, with an average flight time of 3h 04m. The most common departure time is 07:00 and most flights take off in the morning. Each week, there are 181 flights. The most frequent day of departure is Monday, when 14% of all weekly flights depart. The fewest flights depart on a Saturday.