I think, and I may be wrong, that the Pipes/Tobacco section was intended to be somewhere along the lines of your favorites.. Like so
Pipes: A registration era Stanwell Canadian, Castello Searock Bent Billiard
Tobacco: Penzance and other heavy English.
Anyway, Chicago has turned into more than just a weekend to buy/sell wares... For all intent its hit the week long mark, with everything from fancy diners, meet & greets, carving seminars, The Smoke Tent (which seems to have turned into a place a man could happily spend a lifetime, a Valhalla for pipers? ) And about a 1000 other things to do...
Plus there's other 'shows' that are starting to follow suit...
Columbus Oh, Richmond Va, New York, Kansas City, and the Northern California show are all exciting with plenty of good food, good company, oddles of 'Pipe Celebrities', plus a couple truck loads of pipes/tobaccos/tampers/lighters/etc... I think if you attend one you'll get your 'Convention' bug sated.