We were out at Kuipers Orchard yesterday, we just bought apples from their country store but the have a very large orchard (150 acres) and grow about 20 varities that you can pick. They make a huge production and have hayrides, a large corn maze, petting zoo, a country store and fresh baked pies and food. There was probably over a thousand people there but all is handled smoothly. See link below for directions and times.
I suggest Cranes Apple Orchards in Fenville, MI. A nice weekend getaway, spend the night in South Haven or Saugatuck.
Good apple picking, and a great pie pantry. There were more IL plates in the parking lot on Columbus Day than an other vistors.
Not sure what the status is of the apples after the snow they got there last week. Either way, they will have apples to sell, and you can't beat the pie they sell.
You may be late to pick fruit ... a number of the orchards close immediately after the first hard freeze.
The orchard that I recommend is Royal Oak Orchards in Hebron, IL (http://www.royaloakfarmorchard.com/). They also have a good number of baked goods and an excellent restaurant. They are closed on Sundays.
We like Currans just west of Rockford: http://curransorchard.com/, about 1:40 from Chicago.
They have good apples and products, including excellent cider donuts that rival the Oak Park farmer's market. The trees are low enough to the ground that even our youngest can pick and/or climb. Plus, they are a low-spray farm.
Depending on what your idea is of close is Edwards' Apple Orchard in Poplar Grove Il just off Rt.173 has it all. Fresh cider, pick your own or they pick apples, petting zoo, hot fresh cider doughnuts and apple pie and live music on the weekends. Not to mention apple butters cheeses and other treats. They also do a fine business in crafts. The place is a part of almost every family in the area and the fall season is not complete with out a trip to Edwards'.