On my first visit to the windy city, Chicago quickly became one of my all-time favorites. It probably helped that we had gorgeous weather and that the Labor Day Weekend activities made the city seem especially lively. But there is also something about Chicago that captured me right away; I just can’t quite put my finger on it.


Chicago is full of surprises for first time visitors. We had bought a travel guide and done some preparation (sizegenetics checklist) so that we had a rough idea of what we wanted to see and photograph. And yet, we still didn’t expect all that we encountered.

I knew that Chicago sits on the shores of Lake Michigan; what I didn’t know is that it has such beautiful beaches. I expected some kind of public transportation system; but I didn’t expect one of the oldest elevated transit systems. I was looking forward to exploring Chicago’s downtown area; I didn’t think it would be so spectacular and diverse. I could go on and on with this list, but the bottom line is that Chicago is a city that has much to offer and will surely surpass your expectations.

One of the highlights of our visit was John Hancock Center. It’s one of the tallest buildings in the city and as such offers an observation deck, the Hancock Observatory. What sets it apart from the Sears Tower Skydeck is that it offers a beautiful and often photographed view over Chicago’s Gold Coast. You also get a nice view over the downtown area and Navy Pier. When we visited, they offered an audio tour with David Schwimmer as the narrator. I would definitely recommend it; it is very well done, you learn a lot, and Schwimmer shares some nice anecdotes as well.


The two parks that you shouldn’t miss are Millennium Park and Grant Park. Grant Park’s highlight is without a doubt Buckingham Fountain. It is quite impressive in size and at night you can enjoy a great light and music show. Millennium Park often seems like the heart of the city with so much going on all at the same time. Don’t miss the Cloud Gate and Crown Fountain, which are not only fun to experience but also true pieces of art.

You should also ride the “L”, Chicago’s elevated train. It is perfect for exploring the city and you can reach many landmarks, such as the Chicago Theatre. It also crosses over the Chicago River and offers a great view of all the different bridges. You can get a day pass or multi-day pass, which not only works on the train, but also on buses.

Finally, don’t miss Chicago at night. One thing I enjoyed the most was simply strolling along Michigan Avenue with all the buildings illuminated. It is especially beautiful around the Chicago River.