Chicago Boat Show

I own powerboats however do enjoy the occasional sail.

It really depends on what you're looking for. There are usually a few boats there up to 40ish feet and maybe 8 or so aisles of the usual equipment and gear displays. It is by no means a huge show. Even before we lived in IL, friends and I would usually make the 2 hour drive and take it as an opportunity to spend a night in the city/fancy dinner etc and do a bit of "winter boating" in our cold climate. If you look at it like more of a reason to visit Chicago and swing by the show, you won't be disappointed. If you're envisioning a hardcore sailboat show, you may not be as impressed.

Max