Chicago – America’s second city

Chicago was a total surprise. I’d only booked three nights there, but thanks to a generous helping of sleep deprivation we managed to see the highlights. What a fantastically fun and surprising city! The people are seriously friendly, and the diverse culture is reflected in a multitude of delicious eateries and boutiques.

On the water

Being yet another American city built around the water, we took a boat tour onto the river and Lake Michigan. The best part was the detail around the architecture. And this is why Chicago was unlike anything I’ve seen before on our trip – it’s my first city of skyscrapers.

Higher and higher

My neck hurt from looking up the whole time. I’ve never seen so many incredibly tall buildings so densely packed. Imagine the Johannesburg CBD and triple the height of every building. We went up the Sears Tower (now renamed the Willis Tower thanks to a recession property sale), which is still the tallest building in the Western Hemisphere. 103 floors of gleaming steel and concrete, it welcomes over 1.3 million tourists to its skydeck every year.

View from the top of Sears Tower

The dizzying architecture, bustling streets and vital business dealings are why Chicago is referred to as America’s “second city”, the “first city” being the more populous New York. Once a derogatory term, Chicagoans are now proud of this. More than one told me that they have everything New York has, but Chicago is “less intense” and “more laidback”.

The original Playboy mansion (before Hef headed west)

“Second City” is also the name of Chicago’s improv comedy troupe where many legends got their start, including Alan Arkin, the Belushi brothers, John Candy, Steve Carell, Tina Fey and Mike Myers. Al and I were lucky enough to catch a highly amusing 4pm show (just pitching up at restaurants and shows an hour before has actually worked pretty well for us). I’d never watched improv before and now I love it. When the actors are good, the humour is even funnier for its raw authenticity.

Funny Alistair in front of funny people

Then there is the food. We tried the famous deep-dish pizza, as well as Polish sausages and pastries, although my favourite restaurant was the 10:00pm porcine meal we had at The Purple Pig. Their motto is Cheese, Swine & Wine, which I took as an invitation to try the roasted bone marrow pate, pig’s ears with kale, balsamic pig’s tails, pork neck rillette, monte crudo cheese and half a bottle of Bordeaux. By the time we left (after midnight) I was oinking all the way back to our hotel.

Alistair, playing with the bean

On our last day we strolled along Lake Michigan’s beach, watching beach volleyball and rollerbladers, before heading to the famous “bean” sculpture and gardens of Millenium Park.

Millenium Park amphitheatre by Frank Gehry

One thing about American cities – they sure know how to care for and promote their public spaces. It was a sweltering Sunday and children played in the water fountains while their parents relaxed under the trees. Chicago definitely demonstrates how urban living can be quality living. That’s why it is in my top five US destinations.