Chicago – Solo Travel for Introverts – I

Sensory Calm  3 out of 5 stars (3 / 5) – It’s a big city, but definitely more laid-back than New York.

Solo-Friendliness 5 out of 5 stars (5 / 5) – Extremely solo-friendly. Lots of solo activities, and most restaurants had bar seating for one.

Commute Friendly  3 out of 5 stars (3 / 5) –  There is a reasonable spread of public transport, which along with ride-sharing apps are sufficient for travel, but not as extensive as the subway in New York. Having a car is also not a bad idea, since there is enough parking on the roads, and public transport has frequent delays.

Predictability 3 out of 5 stars (3 / 5) – Many places were closed or shut down and this was not updated on their websites. But aside from that, I did not see anything unpredictable.

Safety  4 out of 5 stars (4 / 5) – I never felt unsafe in Chicago. Only, when I went South of the Loop, Ride-sharing became significantly lower, and I was stranded sometimes for long periods of time.

Nerdy stuff5 out of 5 stars (5 / 5) – There are many museums and architecture tours here. Although, the museums are spread out in distance, and require planning with regards to traffic delays and closing hours.

The Loop and the Bean

The city-center of Chicago is called the Loop, as it is surrounded by a loop of elevated train systems, called the ‘L’.

When the clouds parted, I strolled around the Bean sculpture, Millennium Park, the Pavilion and the Waterfront. However, I had to cut this short because of the extremely cold weather (2°C /  35.6°F) and a heavy downpour.

Inside Architecture Tour

Chicago’s architectural wonders were not merely from the outside. The interiors had a lot more to say. I had booked an Inside Chicago walking tour about building interiors, and it was a highly educational experience.

There are 2 styles which I found most interesting:

Art Deco Style

Art Deco is an early modern style that combines minimalism with opulent materials like gold, ivory and marble. Unlike classical designs, Art Deco shows straight geometric lines with sharp angles. It also evokes a sense of verticality and pulls the eye upwards.

European patterns like floral designs are not center-stage, and instead, motifs from ancient Egypt, Persia or Aztecs are given space. Plants, animals and human figures are simplified into minimal geometric shapes. It ultimately expresses an optimistic view of modernity and cosmopolitanism.

Our walking tour showed us the inside of various buildings like the Chicago Board of Trade and the Rookery Building, as examples. We were also told that the Rookery Building was the office of the architect Frank Lloyd Wright, whose Prairie House style buildings can be found all over America.

Neoclassical Styles

Many buildings in Chicago also have the neoclassical influence modeled after French and Italian styles. The city’s many hotels like the Palmer House catered to a European clientele, and entertained them with the likes of Frank Sinatra. The rooms’ designs had to have the appropriate amount of excess to match.

Many buildings like the Chicago Cultural Center also revive the Byzantine and Moorish interior styles. This one, for instance, has a mosaic style with tiny triangular tiles laid at slightly odd angles, which create a shining effect as the viewer moves around them.

The Art Institute of Chicago

This was hands-down the best art museum I’ve been to. While they had a lot to explore from all cultures around the world across all periods in history, I opted for the “1-hour” brochure which gave directions to the locations of world-renowned paintings. I highly recommend finishing this first even if you have more time, and then checking out the rest of the museum afterwards at a leisurely pace.

There were pointillist paintings of George Seurat, where I could go near to see how the individual points of color were painted, and how they came together to create recognizable patterns, as I stepped away from the picture.

Picasso’s style captured in distorted faces represents all angles of the subject at once – to create a moving effect similar to a modern day gif, according to some interpretations. I noticed that unlike other painters, his brushstrokes, up close, very extremely smooth and uniform.

The wavy distinct style of Van Gogh came from him making paintings from memory and not immediate capture. He also used colors and shapes to show how he felt, as opposed to what he saw. Up close, I could see each brushstroke being deliberate in straightness or curvedness showing boldness, all coming together in the waviness of the picture.

This was only part-1. More to come on Chicago in upcoming posts, hence stay tuned !!


  1. Amazing! I’ve never been to Chicago but Ive heard many great things about it! 😊 The architecture and building look fantastic!

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