Please be aware that Chicago has multiple airports and that these results are only for O'Hare International airport.
The best day to arrive at Chicago is Saturday and it would be best to avoid Tuesday, as prices are on average 221.93% higher than on Saturday. (Average prices, based on 204 datapoints.)
At Chicago the most flights depart around 12:00. (Hourly flights, based on 383 datapoints.)
From Chicago most of the flights depart to New York, second best connected from Chicago is Toronto. (Daily flights, based on 118 datapoints.)