I live in Evanston IL, and there are many, many cool small businesses that you should consider putting on your list. You can trust me because I've lived here for over half of my life.
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Shopping
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Food
Shopping
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This is my favorite small bookstore ever. It is so cool and has so many different sections with amazing books. The basement is the best part, with YA books, adult fantasy, romance, mystery, and a used book section.