In general, when booking your flight to Chicago, March is the cheapest month on average.
From most locations, booking your flights to Chicago around 14 days prior to your departure date finds the best deals.
On average, the cheapest flights to Chicago are found when departing on a Monday. Try to avoid departing on a Sunday, as this is usually the most expensive day.
In general, when looking for the cheapest flight to Chicago, our data indicates that morning flights are the most cost-effective. evening flights tend to be the most expensive.