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Chicago: Cold Feet & Hot Beef (Don't Ask)

@Leo Carter3/14/2026blog
Chicago: Cold Feet & Hot Beef (Don't Ask)

okay, so chicago. it’s…a lot. i landed with this weird feeling, like i’d accidentally stepped into a movie. not a good movie, necessarily, but one with a really interesting soundtrack. the numbers 4883555 and 1840011243 keep popping into my head, which is probably just jet lag manifesting as prime numbers.

a grassy field next to a lake with trees


i’m a vintage clothes picker, which basically means i wander around looking for things people regret buying. chicago is perfect for that. seriously, the thrift stores here are legendary. i spent a whole afternoon in Wicker Park, and i think i found a 1950s bowling shirt that’s going to be my new signature look.

the weather? i just checked and it’s…actively trying to freeze your face off, hope you like that kind of thing. the data said 1.93 degrees Celsius, feels like -2.3, with a wind chill that’s probably plotting my demise. but honestly, it adds to the vibe. you need a good *coat, a scarf, and a healthy dose of denial.

i overheard someone at a
coffee shop (more on that later) complaining about the lake wind. apparently, it’s a local legend. they said it carries the spirits of disgruntled stockbrokers. i’m not sure if i believe that, but it’s a good story. speaking of coffee, i found this tiny place called Intelligentsia Coffee - it’s seriously good. https://www.intelligentsiacoffee.com/

“Don’t even think about ordering deep dish pizza if you’re on a first date. It’s a commitment.”


that’s what the barista told me. apparently, it’s a messy affair. i did, however, try the
Italian beef. it was…an experience. messy, glorious, and definitely requires a nap afterwards. i saw a review on Yelp about Al's Beef (https://www.yelp.com/biz/als-beef-chicago) that said it’s “life-changing.” i’m not sure about life-changing, but it was definitely worth the heartburn.

a close up of a tree branch with leaves


the people here are…direct. let’s just say that. i asked for directions and got a five-minute lecture on the failings of the public transportation system. but it was delivered with such passion that i couldn’t even be mad. if you get bored,
Milwaukee and Indianapolis are just a short drive away.

i also stumbled upon this amazing record store in Lincoln Park called Dusty Grooves. https://dustygrooves.com/ it’s a vinyl junkie’s paradise. i spent way too much money, but i have no regrets.

“The Art Institute is free on Thursday evenings. Just…prepare for crowds.”


that’s what a guy on the
train told me. i haven’t been yet, but i’m planning to go this week. i’ve also heard rumors about a secret speakeasy hidden behind a bookstore in River North. i’m still trying to find it.

a cell phone laying in a field of grass


someone told me that the
Magnificent Mile is a tourist trap, but honestly, it’s kind of fun to people-watch. and the architecture is stunning. i’m staying in a tiny Airbnb in Logan Square, which is a really cool neighborhood with a lot of bars and restaurants*. you can find some good deals on Airbnb here: https://www.airbnb.com/s/Chicago--Illinois--United-States.

i’m starting to think i might actually like this city. it’s chaotic, cold, and a little bit intimidating, but it’s also full of surprises. and really good coffee. and vintage clothes. and Italian beef. okay, i’m officially obsessed. i'm also checking out some local events on Eventbrite: https://www.eventbrite.com/d/il--chicago/


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About the author: Leo Carter

Connecting dots that most people don't even see.

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