Weird Chicago #AtoZChallenge

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As in years past, this month I’m participating in the Blogging from A to Z April Challenge. 2016 marks my fifth anniversary, so to celebrate, I’m hosting Friday Blog-Ins here in San Diego; you can find out more info about where we’re meeting each week on my A to Z Challenge page.

My monthly theme is Chicago From A to Z, so stay tuned from Monday to Saturday for new posts on the Windy City. Or sign up for my mailing list (delivered weekly, on Fridays) so you don’t miss a thing!


Chicago has plenty of weirdness going on. But, unlike some cities (coughcough AUSTIN cough…), Chicago’s secure enough in its identity that it doesn’t have to flaunt an official “Keep It Weird” motto.

Chicago understands that everyone can be weird, but that only the truly bizarre will stick with it over the years.

And, let’s face it: no one who’s truly weird ever has to advertise the fact.

Your friend who apologizes for being weird? NOT WEIRD.

Cities with mottos like “Keep Austin weird”? NOT WEIRD.

Anyone who spells the word “wierd”? NOT WEIRD.

Here are a few weird things about Chicago that you may or may not already know about…

The Cubs are legitimately cursed

I’m not sure whether an actual witch or wizard was involved or not, but the stats speak for themselves: The Cubs haven’t won a World Series since 1908, nor played in one since 1945 – when the curse was supposedly placed on the team by Billy Sianis, owner of the Billy Goat Tavern.

The team has attempted several times to “reverse” the curse, but it looks like no one can break it.

This White Sox fan is perplexed and bemused by the curse, but still prefers a team with the motto “Good guys wear black.” Sorry, Cubbies.

The ongoing popularity of Frank Lloyd Wright

No offense to the world-renowned Wright, but frankly (harhar) I don’t understand why this architect remains so very popular.

Sure, his houses and minimalist Prairie architectural stylings are cool… but what about his totally crap take on interior design? Tell me you love open office design, and I’ll show you a phalanx of office workers who’d be keen to string you up. Wright basically inspired cubicles, and the drones that inhabit them, so please stop with the incessant fawning. Unless you’re working at a one-woman company, this style is simply not conducive to actual business.

This dining room is the stuff of nightmares:


Who’d want to eat a meal, sitting in such unforgiving chairs? And in such stark surroundings?

Not me, thanks.

And how about a little color, Frankie?!

Wind-speed is not the reason for Chicago’s nickname

Why is it called the Windy City?

You may be surprised to know that it’s not because of the wind (a legitimate concern, particularly during the frigid winters if you’re anywhere near the lake), but because of the hot-air-filled politicians that Chicago received its nickname.

That’s right: the Windy City is so named because of its blowhards!

Additional Resources

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Pre-order your copy today

Like what you just read? Thinking of visiting Chicago soon? Pre-order your copy of my forthcoming guidebook, Chicago From A to Z, for lots more about the Windy City – including local hotspots, tourist attractions, cultural oddities, and anecdotes you just won’t find anywhere else!



  • Michele

    I had heard that about how Chicago came to be known as the Windy City. That’s great!! I love that.

    I agree with you: that dining room is downright scary! Looks like some uptight, rigid, narcissistic crazy folk live there…

    And I have to say, being a resident of Austin for the last 25 years, there is a lot of weird around here. Wonderfully weird though. And I like the city motto. I think it’s kinda cool because we’re proud of our weirdness. We’re not all weird but I can tell you truly, there is some really weird shit happening around here. But it’s all good. It’s like a time warp. Sorry that you don’t like our motto. I do…and I even wear the t-shirt. :)

    Michele at Angels Bark

    • Laura Roberts

      Thanks for commenting, Michele! I lived in Austin a few years back, and I have to admit I didn’t find much weirdness there… except for the insistence that the city WAS weird. Then again, I don’t think I’ve ever nearly been run over (repeatedly) by a dude on a bicycle wearing nothing but a Speedo (thanks for the memories, Leslie!), so maybe I just wasn’t hanging out in the right parts of town. ;D

      • Michele

        Poor Leslie. He died a few years back, did you know? He was a character for sure. But the city embraced him and I thought that was very cool. I can’t recall exactly now all of it but the mayor put out a big statement about his death and the Austin City Council held a moment of silence for him. He even has his own Wikipedia page!

        I envy you though, living in the Windy City where you actually have 4 seasons. I love the attitude of Austin but I hate hate hate the summers here! (I’m originally from Buffalo). I’ve always wanted to visit Chicago and heard that it’s a like a big small-town in attitude and that the people are fantastic there. One of these days I’ll get there…