My visit to Chicago was more than two years ago, at the end of April 2014. I was there as a professional for a conference I was organizing. I arrived on a Monday and the event ended on Thursday evening. So I took the opportunity to extend over the weekend and stayed Friday, Saturday and flew back to Portland on Sunday morning.

I didn’t know much about Chicago. I had asked for some advice and recommendations around me and I had mainly retained Windy City and Deep Dish Pizza! I experienced both and yet I would have done without the first one because the city did not fail in its reputation, there was wind on Saturday, a really icy wind that almost prevents you from walking outside as it paralyzes every inch of your skin with cold.

Chicago was my first “solo trip”, my personal challenge, my 2014 resolution, the goal I really wanted to achieve. I had never “travelled” alone. I do a lot of things alone, but the trip, even for a weekend, was not one of them. But this time Lois couldn’t join me and I really wanted to take advantage of this opportunity to discover this city. So I had taken my courage in both hands and booked myself a room in a hotel with the firm intention of exploring the city. I had booked my room a few weeks before on a hotel comparator.

In hindsight I didn’t do as much as I could have. Because of lack of time, lack of organization, and a little lack of courage to be alone. So you won’t find here a very detailed article but only some pictures of the places I had the opportunity to see.


It is located along Michigan Avenue, the avenue that runs through Chicago from north to south, and on the shores of Lake Michigan.

Its nickname “Bean” comes from its bean shape. It is an urban sculpture by British artist Anish Kapoor located in Millennium Park.

So that was the ultimate challenge I had set myself, because I have a monster vertigo. But still with the idea of “pushing” my limits, I had bought my ticket to go up to the 103rd floor of the Willis Tower and try to enjoy the view. More than two hours of labyrinth and waiting to finally reach the famous attraction and queue up again to finally take a few seconds inside these glass cubes suspended in the void. People were already jostling behind me, and beyond that, my vertigo was taking over. Two pictures of my feet later, I was happy to give way to those who would dare to do more acrobatic figures of style than me.

So the view is indeed magnificent. It is said that in super clear weather, you can see the 4 states: Illinois (of course), Wisconsin in the northwest, Michigan in the northeast, Indiana in the southeast. In my case, I only had the pleasure of seeing a nice glimpse of Chicago.

On the right of the picture, behind the lamppost in the foreground, you can see the Trump Tower, named after the billionaire (and future presidential candidate of 2017 – *sadness). This 423-metre high building houses a garage, shops, a hotel, a restaurant and apartments (the price of which I can’t even imagine). Far from having the madness of grandeur (irony inside), Donald had a project to build the tallest tower in the world. That was in 2001. That was before. Before the towers of the World Trade Center were hit by the sad attacks that we all know about. The project was therefore revised (downwards) and the tower was completed in 2009. Nevertheless, the tower remains the 3rd tallest building in the United States after the One World Trade Center and the Willis Tower.


It is the main artery that runs through the city from north to south, along Grant Park and Millenium Park. The BnB I had found was on this avenue, a little outside the centre but close enough for me to walk.

Some recommendations include

  • Dress warmly if you go there in winter (I was there at the end of April and had a nice day and a cold day)
  • Enjoy a Deep Dish Pizza from Giordano’s: no time to take pictures so much that the pizza disappeared quickly!
  • The TripAdvisor City Guide application (free) offers pedestrian routes to discover the city. Super well done! It is possible to download the complete catalogue of a given city, making it accessible even without an internet connection.
  • The Art Institute of Chicago is a must even if you’re not a great art fan, it seems: I didn’t do it and I’m biting my fingers off it.
  • It seems that the 360 Chicago Observation Desk (formerly known as the Hancock Observatory) is nicer and more interesting than the Skydeck in Willis Tower.
  • Not tested either, but I’ve heard a lot about Garrett PopCorn Shops.

Since that visit to Chicago two years ago, I have only one desire: to go back there. I am both happy to have been there and to have discovered it (a little), but also quite frustrated not to have done more. I know I will go back, with my little family this time and in the summer to be able to enjoy it better! Until Next time Chicago!

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