I’ll show you around that toddlin’ town, says Nitin Chaudhary in this whimsical ode to the windy city

It was the 21st successive hour of sleeplessness when I opened the window and looked out of the 16th floor. The world stirred below, wrapped around in a coolness that the city air borrowed from Lake Michigan. It would be so easy for someone to step out of the unprotected balcony and disrupt the methodicalness down there; or perhaps such a spontaneity would only cause a little wrinkle on the Starbucked, Dodged, Obesed, casual Hey, How Are You-ed American life that otherwise flowed seamlessly on.

‘Suicides are on the rise, and officials don’t know why’, says the Chicago Tribune.

But somehow no one seems to jump from the buildings here in downtown even though almost every building is a sky-rise offering this sick convenience. I poured over the statistics in the Chicago Fire Department website – sleeplessness makes you do weird things – to find that the determined ones still preferred the trigger to the cast iron railings.

Somewhere a police siren went off, bringing me back. It was my first day in Chicago, and like a faithful mate my insomnia kept me company for the next eight days. A few hours later I was running on the streets, looking for clues to Americanisms. I found it in the usual places – obese people, Afro-Americans, big portions, massive cars – and in some unusual places as well — listening to the blues, the friendliness both genuine and superficial, and the patriotism of American flags hanging outside suburban homes.

I ran on the lakeshore trail capturing every moment, every oddity. It was Memorial Day weekend, and bicycle marathons and running events followed by open-air barbecues were everywhere. I ran through Millennium Park, took pictures of the Bean, took other peoples’ pictures, walked on the manicured garden around the Shedd Aquarium, and stepped past touristy river-side cafes to go up to Trump Towers. I ran till my legs gave way, for I had discovered that running is perhaps the best way to study Chicago.

“I like Chicago because it’s a true American city,” said Dennis. Dennis is short, medium-built, has bulk around his waist and the air of someone who has seen life go by. He is a cartographer who knows every street and corner of the windy city; he has mapped them all for 15 years from the two-room apartment in Ashburn where he lives alone. We met up accidentally in the Signature Room on the 95th floor of John Hancock Tower. The sun was long gone and Lake Michigan silvered in the full moon. It was just the right time for tourists like me to flock into the vulgarly expensive piano bar. Dennis had just rescued a group of Japanese tourists who had spent a disappointing day scouting for the non-existent Al Capone museum. A $15 cocktail was his reward to himself for picking up unexpected business; he held it tight while recounting the names of 200 neighbourhoods in less than five minutes, on my challenge.

“New York has grown into a mass of bizarreness that no one can comprehend, and LA is like Asia,” Dennis continued, in poetic spate, “It is only Chicago that has not traded its soul.” 1848 is perhaps as important a year in Chicago’s history as 1871 when the great fire defeated the city. It was in 1848 that the Chicago Union Railroad opened along with the Illinois and Michigan Canal. Chicago was now at the cusp of transport trajectories that saw steamboats and sail ships alloy with the railroads, legitimising its transformation into a mercantile city. “To Chicago,” toasted Dennis over the din.

‘Only God Can Judge Me Now’ read a neon billboard outside a pub as I walked out one late evening with a Danish friend. Neon lights are a great American invention, I remember thinking, as this one intrigued us inside. The smell of leather, sweat and beer fused into something potent drifting freely inside; it was a boys’ gathering. “Chicago and Copenhagen have something in common,” the friend said, “we both love our gays”. Boys’ Town in Chicago is a nest to some 15,000 gays and lesbians; Chicago displays a Nordic-like acceptance of homosexuality that would perhaps be uncommon in the middle states.

Next door was Chicago Blues, one of the better known Blues hangouts in the city and our original destination. Literally lit blue, with more neon sparkling and bright, the smallish hole had a big mama occupying the corner platform, singing classics late into the night.

Ain't but one thing… Give me the blues… When I've worn a hole… In my last pair of shoes…

I carried the words for company while walking the sleepless streets afterwards. By now, the 168 waking hours I had spent in Chicago uncannily resembled the feeling that follows multiple espresso shots. I walked to the Bean, glistening from the lights projected from the top floors of the surrounding high-rises. Another canto came to me as I touched the cold metal:

Reach for the stars so if you fall you land on a cloud… Jump in the crowd, spark your lighters, wave 'em around… And if you don't know by now, I'm talkin' about Chi Town. The words by Kanye West are his dedication to Chicago. For that moment I owned them. So I walked some more in Chi City; floating by on the crazy wisdom pieced together from songs and neon signs.

Quick Guide

Must See

Lake Michigan; vast and never ending, worth taking a stroll around

Signature Lounge on the 95th floor of John Hancock building offers an excellent view of Lake Michigan

The Bean, designed by Indian-born British artist Anish Kapoor, in the heart of the city

Must Do

Take a boat ride to see the city’s architecture; highly recommended

Go to a Blues bar, here in the land where the music was born

Forget the map, and discover downtown in running shoes

Must Eat

Garrett’s popcorn. Long queues are a constant outside Garrett’s and you can create your own tin of flavoured popcorn.

Grilled baby octopus at Girl and the Goat; extremely popular with the locals, and tables are difficult to score

Contemporary vegetarian at Green Zebra; a typical meal is six to nine courses!

Coffee at Intelligentia; move beyond Starbucks and try some fresh roasted coffee