Chicago’s Best Worst Block

There are lots of places in Chicago where you can go, and with a little bit of imagination, be transported to another time.

A stroll along Astor Street takes you to 1930s flapper-era Chicago.  A walk down Prairie Avenue takes you to the late 1800s railroad baron-era Chicago.  And wander around the West Loop for plenty of glimpses of 1940s industrial-era Chicago.

But have you been to the 400 Block of South Clark Street lately?  To us, it’s our favorite Chicago block.

400 block South Clark Street

That’s because it transports you back to late 1960s shithole-era Chicago.  A time of hot summers, dangerous music, bully cops, cheap beer, aggressive pimps, ghetto sled Cadillacs with curb feelers, crime, grit, and an electricity in the air like the whole city could explode at any moment.  This is the dirty Chicago that The Blues Brothers only hinted at, but somehow still glamorized, skinny ties and all.

The west side of the block is a perfect storm of sketchy establishments: A liquor store, a fish and chicken shack, a pawn shop, a payday loan joint, a flophouse, and the secret sauce: A jazz club.  Somehow even the cell phone store doesn’t seem out of place among the sputtering neon signs, grimy concrete, and metal accordion storefront gates.

The 400 block of South Clark is the opposite of modern-day downtown Chicago with its dog parks and Trump spires and cupcake boutiques.  This block should be a must-visit for all tourists.  But only in the dark, and for best effect — after a quick burst of rain on a sultry night to bring out the stench of stale urine.

Then once the tourists have had their fill taking artsy photos of the “Loans on any article of value” sign peeling off the brick facade, have them turn around because they’re standing right underneath a 27-story federal lockup.

Most cities don’t appreciate their landmarks until it’s too late.  Chicago should preserve this craptastic piece of its living history the way it does with Frank Lloyd Wright districts.  It shows the city how far it’s come in the last few decades, while reminding us that this is still the every-day reality for so many thousands of our neighbors being left behind.

What’s your favorite Chicago block? Tell us at the Chicago Architecture Forum.

Author: Editor

Editor founded the Chicago Architecture Blog in 2003, after a long career in journalism. He can be reached at

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  1. Time capsule indeed! But, what did you expect since the Metropolitan Correctional Center is just across the street? It’s spooky enough during the day; I would send my worst enemy to that area after dark.

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    • Perhaps the Museum of Science and Industry could be persuaded to acquire the frontage, as a companion piece to the venerable Yesterday’s Main Street. “Yesterday’s Skid Row,” anyone?

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  2. I believe this block was also the original Chicago Chinatown, another reason to preserve it.

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    • Editor

      Funny! Just two days ago I was in Chinatown explaining to someone why there is so much Italian influence there, and explaining how Chinatown used to be in the south Loop. I didn’t remember that this article was scheduled to run today.

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  3. The La Cocina sign is a holdover from the Chinatown era.

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  4. It’s nice that downtown is cleaner, but sad that in the process, downtown lost its uniqueness. Now, locally-owned restaurant have been replaced by Corner Bakeries and it’s hard to tell the Loop apart from Woodfield Mall. I’m sure alot of this is just nostalgia on my part, but I miss the chaotic jumble of pre-suburbanized downtown.

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    • Editor

      I agree. It seems that these days if you want to support a local eatery in The Loop, the closest you can come is to support a local chain.

      There are a few local joints left to haunt. Here’s the ones I go to — Some are better than others, but they all at least have that “old school” Chicago feel to them.

      – Italian Village (not just for special occasions)
      – The Exchequer
      – Cavanaugh’s
      – The Marquette Restaurant
      – Boni Vino’s Restaurant
      – That little Greek diner next to Saint Peter’s
      – Cardozo’s (in the basement of 170 West Washington)
      – Eggy’s

      You could add Miller’s Pub to the list, except that I don’t go there. i went once and didn’t really like it. IMO, Exchequer is pretty much the same restaurant with better service.

      I went to Cafe Artiste once, but thought it was very overpriced.

      Eleven City Diner tries too hard, and is overpriced for what you get.

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    • AMEN! I agree for sure. It’s sad how suburbanized cities are becoming.

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  5. You forgot about G&G’s at Adams and Wabash. Total shithole in the wall kind of greasy spoon that Chicago doesn’t have enough of anymore. On the rare instances that I end up in the Loop, I eat there without fail.

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    • Editor

      Sounds familiar, but I can’t quite place it (and Google street view is of no utility). Is it one of those greasy fish joints? You’re braver than I am!

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    • J and J’s Fish and Shrimp*

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  6. The block does contain another bit of Chicago lore. The pawn shop at one time was home to the “Workingman”s Palace” one of the headquarters for Chicago alderman and one of the Lords of the Levee Mike “Hinky Dink” Kenna. He had nickle beer a free lunch and the upper floors served as a flop house. A lot of elections were won because of this joint. We have a video that features it and another of Kenna’s joints that’s just around the corner.

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    • That same pawn shop (assuming you’re referring to the one visible on the left side of tho photo) is now the set of Hardcore Pawn: Chicago on trutv

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  7. I am pleased to report that as of January 2018 this block has retained all of its seedy glory.

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