H & I can't decide on where to go for our anniversary in a few weeks. He tossed out Chicago and we're definitely leaning that way. As of now, we'll be there from 9/7-9/10 (Thursday evening to Sunday afternoon), but we may do Friday afternoon to Sunday instead.
What do we need to do? Where do we need to shop/eat/visit? Hotel recommendations? We'd like to be somewhere in the $2-250 range for per-night. We're a 3-4 hour drive away from downtown, but we aren't sure if it's worth having our vehicle or if we'd be better off looking into taking the train and then using public transit as needed.