Chicago Diaries

Last week, I visited Windy City for the first time for five days to attend the Laver Cup, an exciting new tennis tournament (yes I love tennis but no I do not play). It was a unique, thrilling, and time consuming experience, but I managed to find time to hit up some other spots around the city.


Millennium Park

Staying right in the heart of downtown allowed me to reach the park in less than ten minutes by foot. As my red-eye flight was scheduled to arrive at 5 am, I had the brilliant idea of visiting Millennium Park at 6:30 am to get pictures of the famous Cloud Gate (The Bean) with hardly anyone else in the shots. That plan was quickly abandoned as my flight was delayed, and delayed again, and I didn't make it there until about 9 am. It was still incredibly cool, especially the view from underneath it. I also got to explore Crown Fountain, Jay Pritzker Pavilion and Lurie Garden. As far as urban oases go, it was an extremely well designed one and would be perfect for an idyllic afternoon in the city.


As essential as visiting The Bean may be, did one even visit Chicago without a picture on a glass on top of a skyscraper? After visiting Taipei 101 this summer, I checked off another world famous skyscraper by visiting Willis Tower Skydeck. The line was minimal on a Thursday evening, even though it was a beautiful day. I was able to sit on the glass without freaking out too much. Just don't look down too carefully.

Wicker Park

For a little escape from the bustling Downtown, my friend and I ventured out to Wicker Park for an afternoon where we strolled along Milwaukee Avenue. With too much to catch up on in our lives, we only got to explore a few of the many eclectic shops - Myopic Books, Volumes Book Cafe (a bookstore and coffee shop in one, such a good idea!), and Kokorokoko. It was lively but relaxing.

Art Institute

The Art Institute of Chicago is one of the most renowned art museums in the world, and the reason is apparent. I only found time to visit on my last day and three hours wasn't nearly enough. There were so many pieces that I recognized from different eras and styles. Anyone who enjoys art would find something that thrills them.


Right in the heart of downtown, Chicago Riverwalk is a great place to stroll along and soak in all of Chicago's most representative architecture. Several people recommended that I take a river cruise to learn more about the architecture, but I couldn't squeeze it into my schedule. I'd love to go back one day for it. There are a lot bridges that allow easy access between the north and south of the river, a lot of them filled with history.

I love visiting all new places. For a place as famous as Chicago, it is even more interesting because it allows me to compare and contrast my preconceived notions of it with the reality. From the skyscrapers to the lively theater scene, I was surprised by much like New York Chicago was. I got a glimpse of its "personality" outside of the downtown by visiting Wicker Park, but I know there is so much more to see. I'd most definitely be willing to go back for more.

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