Chicago is a great place to live but definitely not a snowboarders paradise. $550 for a season pass at Wilmot is steep. But at least it is somewhere to get your fix. I only visit there once a season. The only hill I would visit with some regularity is Alpine Valley (3-4 times a season). At least they have 3 high speed lifts so I can get up the hill more often. I'd go crazy hitting the same terain over and over. Usually I hit multiple hills in WI and MI and I try to squeeze a trip out west if time and funds permit. A season pass for me is not worth it.