It depends on what you're looking for. There are plenty of Airbnb's in the area. We are working on a room block, check out the travel page.
About an hour and a half.
Train or car. There is a train that runs from Union Station to the suburbs depending on where you choose to stay. You can rent a car or Uber as well. Please note, you will need to Uber or take another train from ORD to Union Station.