Review: The seven art & architectural wonders of Chicago

Francesca Specter
Yahoo Style UK deputy editor
Chicago skyline aerial drone view from above, lake Michigan and city of Chicago downtown skyscrapers cityscape, Illinois, USA

Whether or not you have an architecture degree or any formal education on the subject, you would be hard pressed not to enjoy the architectural beauty of Chicago.

Called “The Windy City” not – as it is commonly thought – for its weather but actually because of how much its residents are said to boast about the city. Yet, it more than lives up to praise.

During my visit to Chicago at the end of last year, I had my eyes opened to the city’s wealth of artistic and architectural landmarks.

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While I went in admittedly without much knowledge of any of the below, it was a truly educational – in the best possible way – experience, and one accessible to all.

Here are the sites you need to know about:

The Frederick C Robie House

It boasts the Frederick C. Robie House, a building designed by architect Frank Lloyd Wright showcasing his key features.

The house is now protected by the Frank Lloyd Wright Organisation and is a U.S. National Historic Landmark, and is considered to showcase the architect’s early Prairie style aesthetic, with its open-plan interiors, geometric features and long window panels.

The Peninsula Chicago

This five-star hotel is located in a high-rise landmark building based in the centre of Chicago, on Michigan Avenue. No matter how many times you walk through the hotel’s lobby, it never fails to take your breath away – with the towering ceilings and opulent gold and white Asian-inspired decor.

Staying there during my time in Chicago, I was lucky enough to wake up to incredible views of the city every day thanks to the floor-to-ceiling windows, while the room itself was like nothing I’d ever seen before – with its intricately printed wooden panels and calming blue accents.

The Willis Tower

Once the world’s tallest man-made structure (until the CN Tower in Toronto stole the title), the Willis Tower is the pride and joy of Chicago’s skyline.

Chicago, Illinois, USA - 2019: The view from the Willis Tower, a 110-story 1,450-foot (442.1 m) skyscraper in the downtown district.

The 103rd floor of the Willis Tower features the Skydeck, a pair of clear observation boxes where you can effectively hover over the city’s surface. 

Chicago’s First Lady Cruises

While this isn’t a physical site itself, the First Lady cruise has to get a mention in any architectural guide to Chicago, for the sheer scope of what you see while sailing along the river.

Millennium Park

Museum Of Contemporary Art (MCA), Chicago, Illinois, USA

This is a public park on the Chicago waterfront, providing a burst of verdant space in the middle of the otherwise urban landscape.

Voted the city’s top tourist destination in 2007, the park features a variety of public art and is the perfect space to retreat from the hustle and bustle of the city.

Art Institute of Chicago

Arguably one of the best and most comprehensive art museums in the world, the Art Institute of Chicago boasts famous works including Edward Hopper’s ‘Nighthawks’ and Pablo Picasso’s ‘The Old Guitarist’. 

My only advice is to schedule in a full afternoon to this experience, in order to absorb all it has to offer – or you might even want to visit twice.

Frederick C. Robie House


The MCA, or Museum of Contemporary Art Chicago, was founded in 1967 and is one of the world’s largest contemporary art venues.

It was recently host to Virgil Abloh’s ‘Figures of Speech’ exhibition, the first museum exhibition devoted to the fashion designer and visual artist, whose work is inspired by his studies conducted as part of his master’s degree in architecture from the Illinois Institute of Technology.

A pop-up store featuring exclusive collections inspired by the exhibition remains on the fourth floor of the museum.

I was hosted by Visit Chicago for this trip, and stayed at The Peninsula Chicago Hotel.