Ten reasons why Chicago is the best city in the US



David Whitley rates Chicago as his favourite city in the US – and here a ten reasons why.

Architecture: The birthplace of the skyscraper looks undeniably astonishing. And that applies to both classic old-school towers like the Carbon and Carbide Building, and newer additions such as the corncob-esque Marina City. It’s somewhere you’re never going to get bored of going on architecture tours.

The glass art: The buildings don’t just look amazing from the outside. Go inside a few, and you’ll often find extraordinary decoration, sometimes the handiwork of the Tiffany Glass Company. These include the giant coloured glass dome in the Macy’s department store and the gorgeous, story-telling glass mosaics inside the Marquette Building.



The ‘L’: Rattling around these fine buildings is the world’s coolest public transit system. The elevated trains – or ‘L’ – have a rickety rollercoaster feel to them, but it is undoubtedly an impressive spectacle watching trains shaking along just above street level.

The neighbourhoods: Those trains head out into Chicago’s neighbourhoods, which tend to have a different character from the centre. Pilsen has a strong Latin influence and dozens of murals; Logan Square is creatively hipster; Wicker Park has come out the other end of its hipster phase and now is just a great place to shop, eat and drink. And those three are just scratching the surface.

The attitude: It’s a big city, but it’s also midwestern. And, on the whole, Chicago feels remarkably unpretentious. It doesn’t really care what you’re wearing – and it feels several times less intense than Manhattan or judgemental than LA as a result.

The public art: Millennium Park is an absolute belter – with the spitting faces of Crown Fountain and the ultra-reflective, curvy Cloud Gate competing for attention. Other cities would kill for either, but Chicago has plenty more dotted around. Where can casually drop Picasso sculptures in the city centre?

The blues: Chicago is the birthplace of the electric blues, and still full of monstrously atmospheric blues clubs such as Rosa’s Lounge where old timers will pour their hearts out, hit the harmonicas and get feet tapping along to the twelve-bar.

African-American heritage: The blues came to town when African-Americans came north looking for work. Many of them ended up working on the railroads, and the Pullman Porter Museum tells this story – plus the more important one of how the porter organised and fought for civil rights.

The Field Museum: It’s famous for its dinosaurs, but the Field Museum is vast and covering multiple topics. What’s special about it, though, is the way it builds cool stuff into grander, well-presented narratives. For example, those massive dino skeletons come in half way through a huge, interactive section about the development and evolution of life on earth.

Laughs: Chicago is a fantastic city to see live comedy, especially when it comes to the legendary Second City club, which can count Steve Carell and Tina Fey amongst its alumni. It may be a relatively unpretentious place, but it absolutely knows how to put on a show.

We have some great round the worlds via Chicago here

We have some great round the world hotels in Chicago here


by David Whitley