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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.
In general, most flyers find the cheapest time to book a flight to Chicago is about 32 days prior.
From most locations, the cheapest day to fly to Chicago is Tuesday. Most users found that departing on a Friday was most expensive.
Our data shows that the cheapest Chicago flights are usually those with midday departure times. afternoon flights are often costlier.