"Chicago" Chicago by Kaspian

Chicago Travel Guide: 5,958 reviews and 12,275 photos

Travel Dates: July 31 - August 3 2009.

The Chicago I'd always envisioned was one trapped in the late 1960's: a sooty metropolis of rusting overhead railway trestles, a city of Fedora hat wearing gangsters and ghettos booming with electric blues music in the summer heat. I'm sure all of these preconceptions had their place in time, and although they're not exactly the Chicago of today, there are still thin undercurrents of this past history lingering everywhere. ...A black man on a subway platform with a Fender Telecaster guitar plays a slide version of U2's "Where the Streets Have No Name," as another man wearing a bright purple zoot suit passes him by, pausing momentarily to throw some coins into the open guitar case and give the other an approving nod.

And What I Found...

Was a very clean city; sometimes eerily so: the sidewalks are litter free, the people courteous and healthy, the public transportation efficient (albeit slightly confusing with that whole "Loop" thing). Recorded messages often boom in this town telling you all the things you shouldn't be doing. This image seemed in stark opposition to a trip we made to the South Side for soul food. Everything there seemed just as nice, clean, and safe as the rest of the city until I told my friends I was walking up the street to buy a pack of cigarettes. They scowled at me, "Danger! Danger!" I offhandedly dismissed this and walked across the street and entered the store. Standing behind bulletproof glass, the clerk's jaw dropped when he saw me come in. ...And then he dropped what he was holding in surprise. A young girl working behind the counter also stared pie-eyed in astonishment. "Uhhh... Can we help you?," they asked in unison. "Yeah, I'll have a pack of Marlboro Reds, please." They looked at each other, "Uhhh... We ain't got those." They stood aside to show me the five brands they did have. "That's OK then, thanks," I smiled, turned, and walked out. My hosts were waiting for me in the car in the parking lot. Shaking his head, David says, "You're nuts--you're probably the first white guy to go in that store ever." "Ever? That wasn't a cop?," I offer. "Yeah, that wasn't a cop," he agrees. I think it's sort of funny.

There are invisible lines racially segregating areas in Chicago and that's something a guy who's hangs out in Toronto just isn't used to . Whether they're bad or just normal now, who knows?

The Incentive And The Temptress

Since the very first time I met her, VT member Dabs had been alternating between hinting, suggesting, recommending, coercing, and flat-out nagging me to visit her in "the Windy City". Several times a year I would get a photo of a Chicago deep-dish pizza (such as the one in the photograph on the right) strategically sent to my e-mail about an hour before supper time. My stomach would growl out loud when I opened the attachment, and I'm sure she was sitting at the other end with a sly grin on her face knowing full well she'd just made someone 500 miles away, in another country, totally ravenous. I honestly think she missed her true calling as a member of the Chicago Tourism Bureau.

Fast forward 5 years and Dabs gave up on me visiting. ...No more coercion tactics?! Where's the love? Concerned at this change in behaviour, I told myself that I'd successfully resisted the temptation, won the siege, and decided it was finally time to visit and share one of those pizzas in person with my favourite Chicagoan.

Soul food verdict? Unbelievable!!
Pizza verdict? There is not a word in the English language to describe that type of delicious awesomeness. ...And if I found a word to describe it, I'd ruin this page by adding rows and rows of exclamation marks after it.

Recommended Movies: "The Untouchables" (1987).

Pros and Cons
  • Pros:The pizza!
  • Cons:A lot of creepy rich people in sandals with sweaters tied over their shoulders who look like they're on holidays in the Hamptons.
  • Last visit to Chicago: Aug 2009
  • Intro Updated May 9, 2016
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