My co-worker Steven recently returned from a short trip to Chicago, and oh boy can he tell you everything there is to know about the Windy City (the city’s trademark nickname, as Steven so graciously let me know)!
First off, he stayed at an exclusive Airbnb that was right downtown, because that’s the only way to experience a city, he says. His wife wanted to stay in a comfortable hotel that was close to the airport, but he said it was more authentic for them to share a twin bed in a 500 square foot apartment.
Even though I didn’t invite him, Steven followed me to the hot dog cart outside as I picked up some lunch. Just as I was about to load up my dog with some ketchup, he unloaded some extremely useless knowledge on me.
“You know, in the Windy City, it’s a crime to put ketchup on a hot dog. Luckily you’ve got me to let you know!”
As I headed back into the building, Steven continued to inform me of all things he's now become an expert on…like the best times to take a selfie next to the big bean sculpture (even though the real name is actually Cloud Gate; only the locals know that), how you’ll see the funniest stand-up comedy at Second City you’ll ever see in your life (you haven’t seen comedy until you go to Second City, did you know that’s where a lot of SNL cast members come from), and how you don’t actually need to see a show at House of Blues to get into their gift shop!
So, I dedicate this article to Steven, who without his expertise on a city that he just spent 72 hours in, I would know nothing about a city I don’t live in or care about.