Chicago gets my vote. That puts Lawsonia, Erin Hills, Whistling Straits, Cog Hill all within range. Lawsonia wins the value component hands down.
Another choice would be Michigan, although the flights there are going to be more expensive. Fly into Grand Rapids and you have Angels Crossing, The Mines, and the company of Joe Hancock. Or caravan up to Traverse City area and you have High Pointe (Tom Doak's first course), Arcadia Bluffs, and a few other courses that are escaping me at the moment. The Boyne complex has some great package deals, but I don't remember how far they are from TC.