Lady Luck is definitely a Chicagan. There’s no other explanation for the star spangled, once in a lifetime, right-place-right time, pick your jaw up off that flaw’ experiences that were bestowed upon me this week.

Heading in, I’ll admit I was a little nervous. Having not enjoyed the ‘big city thang’ in San Fran, I made a concerted effort not to hoist The Windy City up on a pedestal, instead shooing down like a naughty kitty caught tip-toeing along the kitchen surface; “Get down, Chicago, get down!” Well? I loved it. Phew.


When you’ve got a big city to explore, there’s no sense in diving right on into Downtown. Oh no no. You’ve got to savour the city flavour, get a feel for what it is to live in and around the big smoke before filling your lungs with it. So I began in Lake Forest – a suburb 30 miles North of the centre, on the shores of Lake Michigan. There I stayed for 2 nights with a wonderful family and visited a local school, to talk to a group of 4th graders who were learning about the 50 states (perfect eh?). Lake Forest is… lush. It’s is the kind of place where the Labradoodles are immaculately dressed and the kids hang out at Starbucks after school. Ain’t no Hubba Bubba for 16p in Starbucks kids (when I was a nipper….).


I then scooted round the edge of the city and headed South West to meet a Mr John Vande Velde. For those of you not inclined to follow cycling, or sport at all for that matter, John is one of the original US cycling legends. In fact, he is the original. Competing on the track at the 68’ and 72’ Olympics, he was then the first US rider to turn pro in 1972. Pile on top of that that he managed to produce three kids (Christian, Madelaine and Ian) who have also represented the US in cycling, and it all gets a little silly.

Meeting John was like meeting an old friend – he was kind, welcoming and more importantly, a total dude. And so we just… hung out. Ate pizza, drank wine and put the world back in rightful order through the medium of chat. His passion for the sport is still as fiery as ever, and I could listen for hours to race-tales from an era where cyclists were even greater hard-nuts than they are today. Of course, my timing couldn’t have been better (see – lady luck ‘in the house’). Vande Velde Junior, Christian, having just retired from 15 years as a pro, was on hand to pop over in the morning of my departure. And whaddya know – he’s a dude too. I’d like to have stayed for days at the Vande Velde gaff. In fact, I think I’d rather like to be adopted into the family, although only on the proviso that I didn’t have to give up mine. Joint custody, anyone?


When I finally made it into downtown, I met up with a sister from another mister, who’d flown in from NYC (she is actually a sister, sort of, it’s complicated). As evening fell we dashed straight to Millennium Park, and to the highlight of Chicago’s modern art – ‘The Bean’. I’d been pre-warned this was a prime tourist spot, where out-of-towners amuse themselves by taking ludicrous shots of their grinning faces reflected in it’s shiny surface. Meh. I shan’t engage in such Lemming-esc behaviour, I thought. Fool. NEVER underestimate the power of The Bean. There’s something about seeing the city mirrored at odd angles in an oversized haricot, that’s simply irresistible. We spent a good 30 minutes giggling and snorting like school children, executing the obligatory array of inventive poses.


Like many great cities around the globe (*cough* London *cough*), Chicago has a river running through it. Who knew? I didn’t. But Chicago’s waterway has a dark secret – it used to run in the opposite direction. You what? My thoughts entirely. In a bid to rid Lake Michigan of waterborne diseases, like cholera, a few civil engineering bright sparks set about reversing the flow in 1887. It hurts my brain, trying to understand how they managed to pull off such a feat (you can hurt your brain too by reading about it here). In short – they built a canal, which allowed the river to drain away from the lake, rather than into it. Genius. And a major success. Apart from the residents in the now downstream St Louis of course – who received a flow of watery Chicago poop where there was no poop before. Love thy neighbour? Nothing says love like the gift of raw sewage.


If you want to cement your love of Chicago, take the architectural boat tour. You’ll learn a ridiculous amount, and above all that Chicago is a city is steeped in history. In 1871, a ‘great fire’ caused 6 square miles of destruction in Downtown. Bad news indeed, but like a grimy phoenix, and with the aid of famous architects from around the globe, a new Chicago rose from the flames. These architects flocked to the now blank city-canvas in a bid to leave their mark. They proceeded to fill the city with the most spectacular buildings, spanning a myriad of styles – The gothic Tribune tower, the Art Deco Merchandise Mart (my fave), The curvy groovy Marina city, The Wrigley building and by far the most famous – the 1,450ft Sears tower – once the tallest in the world.

But by far, and of course, my favourite trinkets of truth from the cruise were movie based:

Truth 1 – The Oscar statuettes are manufactured in Chicago (awesome).
Truth 2 – Scenes from ‘The Dark Knight’ were filmed at the old Post office.

I knew it! As we entered the city via the metro system that morning, on steel tracks above the streets, I’d turned to my friend and said “ This reminds me of Gotham city…. I feel like I’m heading towards Wayne Towers.” You just can’t keep a good movie buff down.


The night before I left town, I cashed in a birthday treat from my bro’s – dinner at The Sky Deck, in the Sears (now Willis) Tower. For some bizarre reason, no one else had booked dinner that night. So at a tourist attraction which gets 1.3 million visitors per year – we had the entire deck to ourselves. Talk about million dollar dinner dining. As I filled my face with Giordano’s famous Chicago style pizza (cheese first, then sauce) and sipped on root beer (why did we ever stop drinking root beer in the UK?), I felt I should be getting down on one knee and proposing to my mate.

After that, I thought Lady Luck was all out of tricks. Apparently not. As I left town, they happened to open a new section of the Lakeshore bike path. Cue cycling right into a media circus, an interview with a reporter from the Chicago Tribune and an easy ride out of town. Magic.

I’m now on the shores of Lake Erie, having made my way though Indiana, Michigan and on to Ohio. The weather is just about holding up and the riding is flat (ish) and beautiful. I’m going just as fast as I can, racking up big mile days before I hit the foothills of the Appalachian mountains and get slowed down significantly.

Illinois and Chicago snaps are now up on Flickr here, for your perusal an
d pleasure.

See you next week, kids 🙂