Please be aware that Chicago has multiple airports and that these results are only for O'Hare International airport.
The best month to arrive at Chicago is October and the most expensive month to fly is March. (Average prices, based on 212 datapoints.)
The best day to arrive at Chicago is Saturday and it would be best to avoid Friday, as prices are on average 132.43% higher than on Saturday. (Average prices, based on 220 datapoints.)
The cheapest airline flying to Chicago is Spirit Airlines. They are 98% cheaper than British Airways. (Average prices, based on 252 datapoints.)
At Chicago the most flights depart around 13:00. (Hourly flights, based on 386 datapoints.)
From Chicago it is on average the cheapest to fly to New York and to Toronto. (Average prices, based on 154 datapoints.)
From Chicago most of the flights depart to New York, second best connected from Chicago is Toronto. (Daily flights, based on 81 datapoints.)