Are you thinking of visiting Chicago, but aren’t sure what to expect? Check out my thoughts and impressions following a week in the Windy City…

Visiting Chicago

“Why Chicago? You know it’s going to be freezing” asked one of my co workers for the umpteenth time. Inwardly, I rolled my eyes. Also for the umpteenth time. ‘Why not Chicago?’ I thought to myself.

First time visiting? Here’s a little about what you can expect from a trip to the Windy City… 

Stunning views from the John Hancock Centre at dusk

Do you like spectacular architecture, a delicious and varied food scene, the arts, and a friendly mid-western welcome? If the answer is ‘no’, then you’re probably on the wrong website. If you’ve answered ‘yes’, then Chicago might just be for you. 

What is Chicago like? Aside from a few very obvious things (deep dish pizza, Michael Jordan, skyscrapers), I honestly couldn’t have told you much about the city before actually visiting Chicago for myself. Despite the freezing conditions, it was enjoyable week and I learned a great deal about what makes this one of the great American cities.

Visiting Chicago - The skyline, as seen from Chinatown

Chicago's wonderful skyline, as seen from Chinatown

Chicago shares a number of parallels with my home city, Birmingham. Both cities are often referred to as the ‘second city’. Both are sometimes overshadowed by what are (incorrectly) perceived to be better or more important cities (for Chicago, read New York and LA; and for Birmingham, read London and Manchester). The two cities also share a working class grit, a wonderful culinary scene and an unpretentious air. Naturally, it didn’t take long for Chicago and I to build up a rapport.

Our base for the week was a lovely Airbnb apartment in Noble Square. It’s not a neighbourhood which pops up on those ’10 Chicago neighbourhoods that you must visit’ lists – it’s where real Chicagoans live. Location-wise, it was great – we could easily get to the more popular parts of the city – Wicker Park, the Loop, River North etc. But at the same time it was quiet and felt quite homely. 

The L-Train is a convenient (and photogenic) way to get around when visiting Chicago

At first glance it appears that the Loop is the city’s centre-point – indeed all of the subway and L (elevated) trains run through it. The Loop is home to Chicago’s business district and here you will find gleaming skyscrapers, Millennium Park, museums, theatres and oh so many places to eat. Naturally, you have to check out the Loop, but Chicago is so much more. 

The city itself is made up of 77 different neighbourhoods, each different from the next and with their own sights, tastes and smells. There’s a thriving Chinatown, which is home to 65,000 Chinese residents. In Wicker Park and Bucktown you’ll find hip, independent coffee spaces, boutiques and bars. Boystown highlight’s Chicago’s progressive nature: it’s the first officially recognised gay neighbourhood in America. Pilsen has a plethora of murals and street art. Wrigleyville is home to the world famous Chicago Cubs. There’s definitely a neighbourhood for everyone.

Visiting Chicago - out in the suburbs

Exploring the suburbs of Chicago

Chicago sits on the western bank of Lake Michigan. It’s no surprise that come summer the throngs of locals and tourists are drawn to the water. There are 24 beaches, which stretch along Chicago’s 28 mile shoreline. Water becomes a bit of a theme where Chicago is concerned. The Chicago river system runs through the city and spanned by countless iconic bridges. Along its banks are boardwalks and bars. Makes note to revisit when it’s not -7ºC.

Visiting Chicago - on the water front

Views from the Navy Pier during the late afternoon

One of the things which particularly attracted me to Chicago was the architecture. The city was home to the world’s first skyscraper – all 10 stories of it! Whilst the Home Insurance Building no longer exists – it was demolished in 1931 – the Loop and its surrounds are packed with some truly stunning pieces of architecture. If you are visiting Chicago for the first time, be sure to check out the Rookery Building (the daily tours are informative and will also get you access to its beautiful spiral staircase). A short walk away is the Chicago Cultural Centre, which boasts a stunningly intricate glass Tiffany dome. The photographers amongst you might find the river walk / cruise of interest – both offer a unique perspective of Chicago’s high rises. Alternatively, head up to the 94th floor of the John Hancock Centre for wonderful views out across the city. 

Visiting Chicago - architecture and the US flag

Above and below: a small flavour of Chicago's astounding array of architectural delights (both internal and external)

Visiting Chicago - Tiffany Dome
Visiting Chicago - spiral staircase

Did I mention that Chicago was cold? Fortunately, there is plenty to warm you up! From deep dish pizza (check out the legendary Lou Malnati’s and Pequod’s pizza joints) to copious amounts of bourbon and cosy jazz and blues bars (be sure to check out Andy’s). In Chicago, you are never too far away from the warmth.

Chicago has a rich artistic history and regardless of the form of art that you enjoy, there is sure to be something to take your fancy. For musical lovers, there are plenty of blues and Jazz bars to check out – I had a great time (and probably a couple of cocktails too many) at Andy’s Jazz Bar. The city also boasts a number of theatres and it’s possible to see most of the well known Broadway plays, along with their smaller, lesser-known brothers and sisters. The iconic sign of the Chicago Theatre offers itself for some wonderful night time photographs. 

A long exposure outside the Chicago Theatre

Whilst I found Chicago’s Museum of Contemporary Art somewhat underwhelming, I really enjoyed the Art Institute of Chicago and the National Museum of Mexican Art. My favourite exhibit was a temporary display in the Art Institute, which was hosting an exhibition of Japanese masterpieces. The Institute itself is only a short walk from Calder’s dramatic and divisive flamingo statue, so you could kill two birds with one stone – pun very much intended.

Visiting Chicago - the Flamingo

Calder's Flamingo

Visiting Chicago for seven days afforded me plenty of time to get to know the real Chicago. Was it cold (as my colleagues had repeatedly pointed out)? Yes. Were some days a little bleak? Undoubtedly. Would I do it all again? Damn straight I would (although, maybe next time I wouldn’t enjoy quite so much pizza). 

Visiting Chicago - The Bean

Thinking of visiting Chicago, or have you already been? What are you most looking forward to / what was your highlight? How many pizzas did you manage to consume? Let me know, below. 

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