Travelling from most locations, it is best to book your flight to Chicago during the month of February for the best deal, although there are other times of the year which offer great deals as well.
On average, from most locations, when planning your trip to Chicago, try to book your flight in the region of 60 days in advance for the cheapest prices.
Most of our users find that booking their departure to Chicago on a Wednesday is the cheapest. Conversely, departing on a Monday seems to be the most expensive.
In general, when looking for the cheapest flight to Chicago, our data indicates that noon flights are the most cost-effective. evening flights tend to be the most expensive.