I briefly encountered Chicago in March after three long days aboard the California Zephyr. At that time it was a snow covered, cold and blustery city, but I saw enough to want to come back. With Chicago hosting the last An Event Apart conference of 2008, it was too easy to warrant a return visit six months later, and became the third of my four city tour of the US in October.

Having spent the previous week in the smaller cities of Seattle and San Francisco, I was quickly overwhelmed by the shear enormity of Chicago. Given her size, it’s easy to make comparisons with New York, yet Chicago has a more varied spread of buildings, and whilst there are many skyscrapers, they don’t compete with each other for space as much, giving the streets a less intimidating feel.

I was more surprised by how layered in nature Chicago is. Streets above streets, bridges across rivers and subways that tunnel underground as well as elevate themselves along the central section known as the ‘Loop’. It might have been easy to forget this multi-layering of transportation modes if it wasn’t for the way roads flexed and bounced when heavy traffic passed over them, or how the elevated stations swayed slightly in the wind.

More noticeable was unpleasant smell that followed you around (perhaps unsurprising given the name Chicago can actually be translated to mean ‘striped skunk’). Much of this smell can be attributed to the Chicago River, which was reversed so that sewage would flow down stream rather than out to Lake Michigan (from where the city’s drinking water is sourced). Whilst the river has a beautiful blue tint, it is actually classed as ‘Polluted’ by the EPA – only upgraded from a ‘Toxic’ classification a few years ago.

The highlight of my time, was taking an Architecture Boat Tour, given by the Chicago Architecture Foundation. I noticed the strong architectural style of the city when I was here in March, but I must admit until this 90 minute tour along the river, I was a little naive as to the many celebrated architects and companies that worked on the buildings, as well as the shear breadth of styles used. From Art Deco warehouses of former mail order companies, to modernist skyscrapers of large American corporations (particularly those of Mies van der Rohe and his contemporaries), each building has it’s own unique charm, and I would be hard pressed to pick a favourite.

Newer landmarks have been added more recently, notably around Millennium Park, home to the fun and playful ‘Cloud Gate’ sculpture by British artist Anish Kapoor.

Here again I was able to gaze upon yet more work by Frank Gehry, in the shape of his sweeping BP Bridge and the Jay Pritzker Pavilion (he also design the Experience Music Project building which I saw in Seattle the week before).

Whilst I love the Millennium Dome in Greenwich, I found it slightly irksome that we decided to mark the occasion with a building that is now privately owned, whilst the people of Chicago got an equally useful entertainment venue that is also a beautiful public park and recreation space.

Now to the low lights. Whilst I was warned repeatedly that Navy Pier was to be avoided, I couldn’t help be drawn in by it’s flashing lights, and firework displays. It turned out to be nothing more than advertisers wet dream, an ugly entertainment venue, with attractions unashamedly promoting their corporate benefactors.

The Magnificent Mile, was not that magnificent either. Apart from a few key buildings (John Hancock Tower, Tribune Tower and Water Tower) it certainly didn’t appeal to me. If you are a lover of shopping, I’m sure you could easily get lost in it’s many densely packed malls and large expensive retailers, yet I don’t think it’s that different from any other shopping experience.

Much like Seattle, I’m not sure one or two trips to Chicago is enough to get a real sense of the city and all it has to offer – I feel I’ve only just scratched the surface. I’ll probably wait a little while until I return again, but when I do, I know there will be plenty left to entertain me.