A Weekend in Chicago


When you hear the word Chicago, thoughts like pizza, windy, the Cubs, and the Bears might come to mind. And you would be correct. However, the city has much more to offer than the basic stereotypes it is associated with.

I spent a weekend last fall in Chicago, and I highly recommend going for a long weekend in the autumn. The weather was crisp, and the people of Chicago go all out with their Halloween decorations.

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In my opinion, the best way to see Chicago is to simply walk parts of it. There are the main tourist attractions that one hears about, such as the Cloud Gate (aka the Chicago bean), which are worth the stop. I would recommend going in the early morning to avoid the crowds of tourists.


In Chicago, you will walk for miles and miles, so it is important to have a substantial meal for the day. Even though it is a bit cliche, I highly recommend Giordano’s. Before my trip I had never tried Chicago deep dish pizza, and I am glad I waited until my trip to try it. The pizza was life changing, delicious, and so filling I do not think I worked it off even after a whole afternoon of walking.


Walking around the city you will see some of the famous landmarks of Chicago, including some of their famous murals that have popped up all over the internet recently.

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One item that needs to be on any Chicago bucket list is a Chicago Cubs game. The atmosphere at Wrigley cannot be replicated. As a life long Rangers fan I did not think I would enjoy Wrigleyville as much as I did, but I could not get enough of the team spirit that permeated the place. I booked my trip in June, and by the time October came around the Cubs had made the World Series. Everything seemed to fall into place for me, and I ended up in Chicago at the same time as a World Series game. Although I could not afford a ticket, I went to one of the places directly across from the stadium to watch the game. The cheering, chanting, and camaraderie there is something I will never forget.

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You have probably read this on other blogs, but oddly one of the best free views of Chicago can be found from the window of the women’s restaurant of the John Hancock Center. I thought it sounded weird too, but if you are trying to save some money so you can have a second meal at Giordano’s, this is the best option.


I liked it because it gave me a great view of the waterfront, which I never explored since I was there on a cool autumn weekend.

If you have a more leisurely schedule in Chicago, I recommend the brunch spot The Hampton Social. At this restaurant the air smells like chocolate due to the nearby chocolate factory. Delicious food and chocolate smelling air? Sounds like a great way to end a fun weekend in the Windy City.


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