Most travellers find the cheapest return flights to Chicago when choosing a flight departing in March.
Most flyers found that booking flight tickets 60 days in advance of their planned departure date is, on average, the best time to get cheap flights to Chicago.
In general, booking your departure to Chicago for a Tuesday represents the best deal on airfare. Try to avoid a Saturday departure to stay away from the highest prices.
On average you can find the best deals on plane tickets to Chicago when looking for flights with midday departure times.