Chicago – a guide to the windy city

I spent two weeks in Chicago in January 2012 while loafing around the States. For me Chicago is a city I’d always wanted to visit. The vast industrial and slaughterhouse underbelly of the American Midwest, the tales of politics and prohibition-era hoodlums, home of the skyscraper.

But for me, it was mostly a musical pilgrimage to the home of Frankie Knuckles and Larry Heard, Lil’ Louis and Ron Hardy: the home of house music.

I landed some work writing travel guides for Guidepal, a startup travel guide company that has seen many millions of it’s free smartphone app-based guides to 70+ cities downloaded in barely two years. For two weeks, I Couchsurfed my way around the city. From Greektown, to the Mexican heartland of Pilsen, to the golden onion domes of the Ukrainian Village, I found inspiration, dug out hot tips and found the low down from people I met in the bars and cafes, my wonderful Couchsurfing hosts, Time Out Chicago, Lucky Magazine and many other places. Braving the snow and -15 C temperatures, I spent an enjoyable fortnight (American readers: that means ‘two weeks’) heading out into the huge Chicago metro area, from the Lakeside, to the hipster paradises of Wicker Park, to the home of America’s favourite architect Frank Lloyd Wright in the suburbs, and even a couple of nights deep in Englewood, in tragically neglected, derelict south Chicago. My Airbnb hostess, Annie, swore vehemently that the police were wrong to say it was the ‘worst place in Chicago’.

“Can’t be anything worse than the third worst place in town,” she cackled, flashing her toothy grin.

At 8.5 million people, Chicago is a huge city best seen from the top of the John Hancock Center at dusk, where the lights of the city grid stretch off to the horizon in every direction. By foot or by bike or by the elevated L-train metro system, it’s a great city to explore, with over a hundred varied, characterful neighbourhoods. Chicagoans have a bluff, Midwest down-to-earthyness about them, a welcome relief from Los Angeles and New York City, where practically everyone you meet seems to think they’re the next big thing.

I loved it, and would move there tomorrow. If only winter wasn’t coming around again so soon…

You can find my guide to Chicago over at Guidepal.

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