Find cheap flights to Chicago

When is the best time to fly to Chicago?

Most travellers find the cheapest return airfare to Chicago when booking during the month of November.

When is the best time to book a flight to Chicago?

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.

What is the cheapest day to depart on your flight to Chicago?

Most of our users find that booking their departure to Chicago on a Wednesday is the cheapest. Conversely, departing on a Sunday seems to be the most expensive.

What is the cheapest time of day to fly to Chicago?

Our data shows that the cheapest Chicago flights are usually those with afternoon departure times. midday flights are often costlier.