Even if you're not a fan of the magazine, this is a great event. We've been twice and had a wonderful time. Where else do you get to sample wines from all over the world, many in the 70-100 dollar range! The food is always quite good as well. This year it's being held at the Navy Pier. These events are not overbooked and never get too crowded (unlike Wine Enthusiast's). You get a chance to meet many winemakers and owners.
http://www.winespectator.com/GrandTour/WSgrandtour.html