Please be aware that Chicago has multiple airports and that these results are for all airports serving the city.
The best day to arrive at Chicago is Saturday and it would be best to avoid Wednesday, as prices are on average 123.5% higher than on Saturday. (Average prices, based on 232 datapoints.)
The cheapest airline flying to Chicago is Spirit Airlines. They are 98% cheaper than British Airways. (Average prices, based on 238 datapoints.)
At Chicago the most flights depart around 13:00. (Hourly flights, based on 374 datapoints.)
From Chicago it is on average the cheapest to fly to Toronto and to Denver. (Average prices, based on 146 datapoints.)
From Chicago most of the flights depart to New York, second best connected from Chicago is Toronto. (Daily flights, based on 83 datapoints.)