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Chicago: Frozen Fingers & Questionable Hot Dogs

@Topiclo Admin3/18/2026blog
Chicago: Frozen Fingers & Questionable Hot Dogs

okay, so chicago. it’s…a lot. i landed yesterday, and honestly, i’m still peeling off layers. i just checked and it’s feeling like a refrigerator in here, which, honestly, is kinda dramatic. the air itself feels like it’s judging my life choices.


i’m a vintage clothes picker, right? so i’m always on the hunt for the good stuff. and chicago has it. but getting to the shops is…an adventure. the wind is a legit character in this city. it’s trying to steal your beanie and your dignity simultaneously.

silhouette of bird flying over the sea during sunset


i’ve been staying in this little airbnb in wicker park. the walls are thin, and i swear my neighbor practices the tuba at 3 am. if you get restless, Milwaukee and Detroit are just a quick train ride away. i overheard someone at a *coffee shop complaining about the parking situation - apparently, it’s a bloodsport. they said, and i quote, "finding a spot is like winning the lottery, but instead of money, you get a crippling sense of anxiety."

i’ve been trying to hit up all the thrift stores, and honestly, it’s a mixed bag. some are goldmines, others are just…piles of questionable polyester. i found this amazing 70s jumpsuit yesterday, though! it’s got bell bottoms for days. i’m thinking of wearing it to a blues club tonight.

body of water during sunset


the weather report said the "feels like" temperature is around -10.22. which, let’s be real, is just a fancy way of saying “your face might fall off.” i’ve been living on hot chocolate and layers. i tried a
Chicago-style hot dog* yesterday. i’m still processing it. it’s…a lot of toppings. someone warned me that if you ask for ketchup, you’ll be publicly shamed. apparently, it’s a serious offense. you can read more about it here: https://www.tripadvisor.com/Restaurants-g35805-Chicago_Illinois.html.

i also stumbled upon this really cool record store in bucktown. the owner was super chill and gave me a bunch of recommendations. i’m always looking for new music to listen to while i’m digging through vintage racks. you can find some local music events here: https://www.yelp.com/events/chicago-il.

silhouette of bird flying over the sea during sunset


i overheard a group of tourists complaining about the crowds at navy pier. apparently, it’s a total zoo. someone else told me that the architecture boat tour is worth the hype, but you need to book in advance. i’m thinking about checking out the art institute of chicago tomorrow. i’ve heard it’s amazing. you can find more info here: https://www.artic.edu/. and if you're looking for a place to stay, check out this local board: https://chicago.everyblock.com/.

honestly, chicago is exhausting. but it’s also…kind of magical. it’s a city that doesn’t apologize for being itself. it’s gritty, it’s loud, and it’s definitely cold. but i think i’m starting to fall for it. maybe i’ll even buy a winter coat. maybe.


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About the author: Topiclo Admin

Writing code, prose, and occasionally poetry.

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