If you want a cheap flight from Boston to Chicago, you've got one airlines to choose from. You can use the search box to filter your preferences, but we've found that the cheapest day to fly is 19 / Sep / 2025.
Make sure you use the search options above to search for flights to other airports in Chicago, not just Chicago O'hare International Airport. The more options you look at, the better your chance of finding a cheap deal. Just so you know, the flight typically takes 2 hrs 55 mins.
four flights go to or via Chicago every week. Cheap flights Currently, the cheapest price available is £196. The most popular airline is JetBlue but do spend some time checking all your options – they aren’t necessarily the cheapest airline to book with.
During this peak season, hotel and holiday prices often increase too, so it's best to book early. Or you could keep your fingers crossed and hold out for a last-minute deal.
