Travelling from most locations, it is best to book your flight to Chicago during the month of March for the best deal, although there are other times of the year which offer great deals as well.
From most locations, to find the best deals on airfare, our data shows that users booking 60 days before flying found the cheapest flight to Chicago.
Most of our users find that booking their departure to Chicago on a Thursday is the cheapest. Conversely, departing on a Sunday seems to be the most expensive.
Our data shows that the cheapest Chicago flights are usually those with afternoon departure times. midday flights are often costlier.