22. Eat that extra slice of deep dish
Lou's, Giordano's, Pequod's... you can get it at any of these places honestly, but the idea here is to reach that point where you say to yourself "it is medically inadvisable for me to eat another piece of this". Then you ignore yourself, inhale another piece, and take a seven-hour, cheese-induced nap. Then and only then have you had the full deep dish experience.
You live in the comedy capital of the world. If you take in a Second City performance there’s a good chance you’ll see someone who ends up on SNL one day, or, at the very least, a Sonic Commercial. But the real rush will come when they ask for an audience suggestion and improvise a hilarious scene to your well-timed shot of “marmots”.
This isn’t really one you plan for. It has to happen naturally. Maybe you packed into Old Town Ale House after the Second City. Maybe you’re checking out a friend’s band at The Hideout, or holding court on the Happy Village beer garden. You feel the hunger, and suddenly that glorious cooler appears and you devour a bag full of tamales with green salsa before you even know what happened, and all is right in the world again.
There are innumerate places to get a flawlessly made drink in Chicago, but the most bucket list-worthy has to be the Violet Hour, a temple of cocktail artistry to which many other find Chicago bars can trace their lineage. While most people know by now the mural is actually a not-so-secret entrance, the drinks remain the top selling point. Sit at the bar for a fine view and the chance to maybe pick up a few drops of knowledge so you can drink better at home.