David Whitley hits Chicago, and dearly wishes he could hit it for longer.


Before I’d even ventured above ground, I felt that I was going to regret only having four days in Chicago. The airport seemed exciting – full of weird art – and when I finally got to the subway station, a four piece hip-hop act was putting on the sort of show that should shame most buskers into realising that they’ve got no talent and are better off getting a job stacking shelves at Tesco.


On the flight and train into the city, I’d had the chance to gradually get myself more and more worked up with excitement. If there is one argument for why guidebooks can be invaluable, incidentally, then Time Out’s Chicago tome is it.


Flicking through the pages, I ended up with an ever-increasing list of things I absolutely had to do. Cycling along the lakefront, blues joints, groundbreaking theatre companies, world class comedy clubs, all manner of cool bars in a number of neighbourhoods with distinct characters, going to watch ice hockey/ baseball/ American football... and that was before I’d got on to traditional ‘sights’ such as the museums, big towers and aquarium.


To realise that I’d not got a chance of even beginning to cover a fraction of what I wanted to was somewhat crushing. But it didn’t take long above ground to catapult Chicago instantly to the top of my list of favourite American cities. There are some cities that are spectacular because of their natural setting – Cape Town and Sydney are the classic examples – whereas others are spectacular for entirely man-made reasons. And I seriously doubt that there’s another city in the world with a skyline as impressive as Chicago’s.


Walking through the city is dangerous, purely because you’re often too busy gawping upwards to notice the bus that’s about to plough into the side of you. Whereas somewhere like New York reaches for the sky with an intermittently stunning building between more workaday efforts, just about every block in central Chicago is taken up with something that has an irresistible wow factor.


Then there’s the world’s coolest train network. Chicago does have a couple of underground train lines, but in keeping with the city’s theme of building upwards, most of the lines run on an elevated railway above the streets. You may recognise ‘The El’ from the Batman movies. It rattles along, makes a fearsome noise and looks like it could all crumble to pieces at any minute. But it’s so instantly loveable that you just want to sit on it, riding round in a circle like clapping retard.


The city centre (universally known as ‘The Loop’) is unmistakeably cool, but Chicago bangs on about its neighbourhoods for a good reason. In the evening, I head out to Wicker Park. One main street is full empty shops, which anywhere else would be a grim sight. Here they’ve given them over to artists as temporary exhibition spaces, and as such are full of weird angels and happy-snap photographs. The latter have been taken all around the area on disposable cameras that have been left there by the artist. The instructions are simple – find the camera, take the pics, and send the camera back – a random selection gets put on display. Can any sane human being give me a reason not to like this?


Dinner is taken at a wine bar. I order a ‘flight’ of wines from South America – essentially four generous sample size portions of red wines from across the continent (did you know that Uruguay made wine? I didn’t), to be consumed in order. I tuck into them over stuffed trout, and when it comes to paying the bill, the barmaid says: “I took care of your wine. You’re obviously new in town – welcome to Chicago.”


I suspect a life-long love affair has begun. I may have only four days here, and as I write, I’ve not even left yet. But I’m itching to return.


Disclosure: David was hosted by the Talbott and Elysian hotels, via the City of Chicago (