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Chicago – A Weekend in the Windy City

Before touching down on to Chicago soil I was unsure of what to expect from this American Midwest City and although I arrived after dark, the illuminated views which greeted me upon arrival didn’t disappoint.

Chicago is a modern city with loads of art installations
Chicago is a modern city with loads of art installations

Awake before the birds with a good old fashioned does of jet-lag, I left the hotel and out onto the Saturday morning streets before the world was awake under a dusting of snowfall. It was April so just at the point of shaking off its winter coat.

The ultra cool city of Chicago, Illinois

Chicago, or ‘The Windy City’ as it is well know towered above with its business offices reaching towards the sky. My initial thoughts was the seamless clash of old world and the new. There are remnants of Chicago during the late 1800s, before Chicago went from a city devastated by a great fire, to the world leader in skyscraper engineering and design that it is today.

How to get around
Chicago is actually an easy city to navigate and get around, compared to some cities and has one of the world’s easiest street patterns and numbering systems. For those with limited time the trolley hop on hop off tours are the perfect way to commute. I was happy to use public buses, river boats, subway system and of course by foot. This is perhaps my preferred means of transport in any new city.

What is the must eat food?
Although I managed to eat my way around the city, as well as visiting the largest whiskey bar in the city, no visit to Chicago is complete without a Deep Dish Pizza experience. I use the word experience because it is a true Windy City tradition and locals take their pizza very seriously indeed. Deep Dish has a crust up to three inches tall at the edge, slightly higher than the ingredients, which include large amounts of cheese and chunky tomato sauce. It’s a bit of a beat to reach the end so my advice is grab a couple of drinks to smooth the passage, start with one slice and eat your way around to the end. I loved my deep dish experience and although the taste is pretty epic, it’s also exhausting!

This needs no introduction!
This needs no introduction!

The people
I’ve said this before in previous blogs but American people are some of the friendliest people I have encountered around the world, however the people of Chicago are fiercely proud of their city (with good reason) and will go out of their way to make a traveller’s experience a pleasant one. With their iconic accent and refreshing style I couldn’t have received a warmer welcome.

What to do in the Windy City

What I got up to
Chicago boasts an array of activities to keep the traveller busy but among my favourites was a stroll along the Lake Michigan shore line with the Chicago skyline as a backdrop. It feels very strange to be in the central CBD but to also have that relaxed ‘seaside’ view. I also took an architecture boat trip onto Lake Michigan which helps interpret more than 50 buildings along the Chicago River, revealing how the city grew from a small back-country outpost into one of the world’s most important crossroads in less than 100 years. The Science Museum is a worthy visit and unlike your typical stand and watch museum, the exhibits are fully interactive, you can even walk through a submarine and inside a plane.

The city sits on one of the Great Lakes
The city sits on one of the Great Lakes

To wrap up my weekend, I entered the elevator at the Willis Tower which shot up 108 floors to the viewing platform offering 360 degree views. There is interesting information available on how Chicago became the city it is and glass floor viewing platforms where you are suspended high above the city with only glass separating.

Up inside the Willis Tower looking down
Up inside the Willis Tower looking down

I always judge a place on how easily I could live there, and Chicago definitely ticks all the boxes!

If you want to read some of my other posts on America, click the links:
Hiking to Angels Landing in Zion National Park
The Alaskan Wilderness – Getting back to nature
Dig this, shoot that in Las Vegas
Yellowstone Winter Wildlife



  1. July 19, 2014 / 6:30 pm

    Chicago is an amazing city! The pizza is definitely awesome, but the overall food experience of this city is just spectacularly. I also love that the price is generally very reasonable. And when it is highly priced, you can bet it’s worth it.

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