Most travelers find the cheapest round-trip airfare to Chicago when booking during the month of April.
From most locations, booking your flights to Chicago around 57 days prior to your departure date finds the best deals.
On average, the cheapest flights to Chicago are found when departing on a Tuesday. 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 evening flights are the most cost-effective. afternoon flights tend to be the most expensive.