I spent time in downtown Chicago as a teen and college student, and walked by Iwan Ries many times there on Wabash, but never went in. Cameras were my obsession then, and I didn't smoke. However, I've been an IR customer online for many years now, have bought a number of pipes from them, and some tobacco, and most recently a sampler of cigars, a variety pack of a dozen "dog walkers," small cigars but not cigarillos. i'm smoking one at the beginning of each month this year.
IR has a vast inventory of pipes, so their online selection and their paper catalog barely scratch the surface. If there is something you are looking for, give them a call. I think their inventory is about 15,000 pipes.
IR is sort of the mother church of pipe shops, dating back to 1857. They own the building, but moved upstairs to lease out the expensive street-level retail space. Smart business. I loved the Nat Sherman shop on 42nd St. in NYC for its size and atmosphere and attentive staff, but IR is far older and has outlasted the now-closed Nat Sherman. IR is a real pilgrimage for pipe smokers. Not everyone's "thing," but I love their old classic aromatic blend Three Star Blue.