Best Used Bookstore
Chicago has one of my all time favorite used book store, Myopic books, 1564 N. Milwaukee Ave, right at the Damen Blue Line stop. Beyond it's huge selection one of its perks are the opening hours, everyday but Sunday until 1AM.
Best (affordable) View
When the weather is nice, the Hancock Tower offers the best view over the city. Going up to the observatory, however, is expensive. Alternatively, you can enter at the (south) side entrance and take the elevator to the Signature Lounge, just one floor below the observatory. Drinks there are pricey, but very good and still cheaper than the observatory.
Amy Sings at @tmosphere
At the North End of the trendy Andersonville part of North Clark, you will find a small gay bar/café called @mosphere, 5355 N Clark St. While this is normally an unremarkable bar, almost every Wednesday night from 9.30pm singer Amy Armstrong performs. Her songs performances - ranging from musical to rock - are great, but just as important are her raunchy (and hillarious) jokes and stories. This together with $12 of Stoli-Lemonade makes for a great night out.
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