Cherry picking season in Illinois begins in late June and runs through the end of July, according to the Pick Your Own and Harvest Time Orchards websites. The amount of time that cherries are good for picking varies from one day to two or three weekends.
At Harvest Time Orchards, which is only 8 miles outside of Antioch, Illinois, the amount of cherries available to pick is based on how harsh a winter the cherry crops had to endure. The harsher the winter, the smaller the crop. It takes about 60 days from when the cherry trees are blossoming to when they are ready to be picked. Once they are ready to be harvested, you pay a "per bucket" price and fill the bucket with as many cherries as fit into it.
If the traditional bucket, which is approximately the size of an ice cream bucket, is not large enough for your cherries, you can purchase a much larger bucket that is about four times the size of the standard bucket. The cherries can then be transferred into containers that you have brought from home, so they are easier to transport. The orchard also supplies plastic bags, in case you do not have plastic containers with you.