Here's my take on the big three shops in the Chicago area:
Iwan Ries is the mother of all pipe shops. There are not many shops like this left in the US. It's on Wacker drive in the heart of the Loop. It's a hassle to get to and has zero affordable parking. Nevertheless, if you're visiting Chicago and you care about pipes... this is the place to go. Huge selection of pipes and an unmatched selection of pipe tobacco. Make life easy on yourself and take the eL train or an Uber to get there.
Up Down Cigar has a lot of character for its size. It's basically an upscale cigar store shoe-horned into a vintage Old Town storefront. You have to give the owner credit for making maximum use of every square inch of space available to them--it's wall to wall flashy and expensive shit. This is the place to go for Chicago north-siders with money to spend but without the hassle of traveling to Iwan Ries. Expensive Dunhill pipes, expensive cigars, expensive knobby canes... they've got it and it's expensive. Not much pipe tobacco but what they do have is going to be premium... Esoterica and Mac Baren all the way. Helpful and friendly staff who are prone to dress like it's cocktail hour. If you're the guy smoking a $50 cigar and wearing a Rolex watch, this is the place for you. On the other hand if you're more comfortable loitering around in ratty jeans and puffing on a corncob of Smoker's Pride... maybe not.
Arlington Pipe & Cigar is a great suburban shop... comfortable, welcoming, and nice large room to hang out for a smoke. Only an okay selection of pipes but the pipe tobacco is the star of the show here... they've got a great selection of tins for sale. This is place is second only to Iwan Ries as far as tobacco selection. You can be the guy with the Rolex or the guy with the ratty jeans and the corncob; whatever way you show up, they'll treat you well.