I was here looking for Tobacco for my father, coming with no knowledge of tobacco at all. The guy who took care of us was really patient and helpful in giving us explanation and deciding what to buy. They pretty much sell almost any kind of tobacco from almost everywhere, of course not Cuban because it is still illegal to sell it here in the US. However, they sell some tobacco that are very similar to Cuban tobacco. Very highly recommended!
The Up Down Tobacco Shop in the Old Town neighborhood of Chicago is located just south of North Avenue on Wells Street. The employees are extremely helpful - when I asked for a specific variety of pipe tobacco, they found it for me immediately, and then recommened an assortment of others based on my tastes. Also, the selection of cigars, luxury cigarettes, and lighters is clearly and ergonomically laid out, so the customer can get a great view of whatever they wish to take home! An A+ experience!