First and foremost, let it be noted that there was no wind while I was in Chicago. I felt let down. Duped. No big apples in New York, no wind in Chicago and now updating my blog on a rainy day in the “Sunshine State”.

Wind or no wind, I shall recount my experiences of Chicago. I realised, upon my arrival, that I had perfectly timed my visit to coincide with the Chicago marathon, pushing hotel rates through the roof and flooding the streets with lycra-clad tourists. I hate tourists. I also hate expensive hotel rooms. People who plan 1 : John 0.

I booked myself into a 4-man dorm in the Freehand Chicago, an upscale hotel-cum-hostel, if such a thing is not a contradiction in terms. I had the room to myself, at least for the first night, so I was a happy chappy. 

The next day was mainly spent avoiding rain and buying a leather jacket for my Route 66 motorcycle trip but dinner and drinks were planned with a friend from Hong Kong, Allan, later that evening. I had some good views en route.

After beer and before tequila Allan told me I had to take the boat tour given by the Chicago Architecture Foundation while I was in town. I promised to do so if I remembered. And remember I did. Luckily.

Tours run numerous times each day and last 90mins. The great thing about this particular tour is that it is run by volunteer docents from the foundation who are both fantastically knowledgeable about the subject matter and highly enthusiastic in sharing this knowledge. As I boarded the boat and headed up to the open-air, upper deck, our docent, a vivacious retiree in a floppy, purple straw hat, was launching into her introduction. And from that moment on I was enthralled.

The various schools of architecture, the city’s history and several amusing anecdotes were all described for us in vivid detail. Hat-lady was a veritable raconteur. Art deco, Modern, Post-modern: we cruised through history, hanging on her every word. The only negative to the experience was entirely my own fault. I had woefully miscalculated the temperature and was wearing a t-shirt that was only just stopping my hypothermia from becoming pneumonia. 

Those of you who have read previous posts on this blog will know that I very seldom do the hard sell on things, however, I feel it would be remiss if me not to do so on this occasion. Please go! If you’re ever in Chicago, go! You’ll thank me for it (yes, Allan, you will be eligible for gratitude royalties).

Another “must” in town is a trip to Portillo’s, the legendary hotdog diner. Prepared to blow my daily recommended calorie intake in one sitting, I strolled over there one lunchtime. The interior is a throwback to 60s diner culture with red, checked tablecloths and Americana littering the walls.

I must confess that I didn’t have the classic hotdog because I was seduced by the beef and peppers roll, dipped in gravy, carrying its own health warning. It was a tastebud triumph!

At around this point in my stay, my dorm-room peace was disturbed by the advent of an obese man who snored like a pneumatic drill turned up to 11. Macbeth may have murdered sleep, but this guy hacked it to death then burnt its body. 

Moving swiftly on, it just so happened that, in addition to the marathon, the city’s baseball team, the Chicago Cubs, had reached the post-season playoffs for the first time in years and Cubmania was reaching fever pitch (pun fully intended). On Friday night, the Cubs were scheduled to play the LA Dodgers at Wrigley Field. Whilst I could not find tickets to the game itself, a group of us headed to Wrigleyville, the neighborhood surrounding the stadium, to soak up the atmosphere. And we were not alone.

We drank anticipatory beers in a quirky little Thai restaurant, we drank game-time beers in a packed beer with big screens and, following a Cubs victory, we drank celebratory beers in an even bigger, packed bar. My last day in Chicago was blissfully sunny and, in the hope that this would be the case, Allan, a friend of his and I had booked to play a round of golf a few miles north of my hotel, on the shores of Lake Michigan. To say I was woeful would be to understate how poorly I played, nevertheless, a version of a broad definition of “fun” was had by all.

My departure from Chicago is also the beginning of my epic Route 66 road trip, so will feature in my next post.