Where & When?

Chicago is home to almost 3 million people and is located on the shores of Lake Michigan, in the state of Illinois, just west of New York.

Although it’s known as the ‘Windy City‘, the weather was perfect in September! I was around for a few days and enjoyed the food, walks along the river and went on a cruise. I found Chicago a lot more compact than New York, and I barely needed to use the subway – I mainly used it to go to and from the airport, but otherwise, I was on foot. Below are a few details of what I got up to, and also check out my Chicago stories on Instagram.

The Skyscrapers!

Cloud Gate – aka The Bean, designed by Indian-born British artist, Sir Anish Kapoor.

Chicago is the home of the skyscraper – there’s no doubt about that when you look around and they are towering all around. The first skyscraper was built in Chicago, and it was the Home Insurance Building, towering at 10 stories high and 138 feet (42 meters). However, it was demolished in 1931, the same year that the Empire State Building in New York was completed, with even taller skyscrapers being built in its place.

Other than skyscrapers and the architecture, what I love about Chicago in comparison to New York is that there’s a river running through it. This makes the city a lot prettier and the green spaces that were created for the River Walk really do make it a lovely space to wander. The River Walk is a space created alongside the river that was transformed in recent years to include green spaces, restaurants, public art and places to walk (and even go for a run). In fact, the local law now states that any building that is positioned alongside the river must create a space for public enjoyment (with the exception of federal buildings). There’s also plenty of opportunities to enjoy water activities on the river from the various stalls set up on the River Walk.

Also, the Navy Pier is worth a visit, which has recently been transformed into a pleasant place to enjoy the evening away from the hustle and bustle of the city. The Navy Pier has been transformed in recent times to include shopping, dining, entertainment and tours. It also is a great viewpoint to enjoy the view of the city skyline as the sun sets!

When I planned to visit Chicago, I decided that I wanted to view the city from different perspectives – from the river, street level and from the top. The River Walk and the cruise along the river allowed me to gain a perspective from below. The Chicago Architecture foundation does really good boat tours, and I recommend them! Traipsing around the streets of Chicago gave me another vantage point and then going up skyscrapers gave me panoramic views of the city from the top. The observation decks I visited were on the top of the John Hancock building, 360 Chicago, and the one on the 103rd floor of the Willis Tower.

A view of the Chicago skyline looking towards Lake Michigan from the Willis Tower

The Food

You cannot leave Chicago until you’ve had a Chicago-style deep-dish pizza, and the first time I’ve ever had one was, in fact, on this visit to Chicago!

An individual deep-dish pizza

These are the restaurants that I thought were great and I visited:

I had one deep-dish pizza a day and even if it’s an individual pizza, it is really filling. In fact, I overheard the waiter saying to a couple on the next table that one “individual” pizza can be shared between two… whilst I was on my last piece! The crust itself is not thick, other than on the edges, and it’s delicious with a generous amount of filling. My mouth is watering even as I type this!

What I also loved about the experience was the ambience and interior of the various restaurants and they each had their own unique character and feel.

The interior in Gino’s East, “Mag Mile” restaurant – I just love the graffiti! #DeepAF


Being an airline pilot that flies the Boeing 737 aircraft, I had to visit the Boeing HQ in Chicago! These are where the corporate headquarters of Boeing are located. There’s no aircraft here or much to see, but I did bag a few items from the gift store!


If you enjoyed my blog, give me a follow on Instagram for more of my travel pics and feel free to message me there!

You’ll also find my Chicago stories, documenting my trip there!


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