I’ve been bitten by the travel bug early on. I “blame” my parents for that. By the time I was 23 I had covered a good part of Western and Central Europe and when my best friend decided to do Master’s degree in the US (in Michigan) I was delighted, as it was a very (very) good opportunity to cross the Atlantic!
On my first trip to the US back in February 2008 (which also inspired me to start blogging), Chicago was the first big city that I got to visit and I don’t regret the fact that I visited Chicago prior to New York! It was very cold for a Greek girl (isn’t called windy city for nothing, right?), but the 0 degrees Celsius didn’t put me down as I was very well prepared! I’d never been to a city which is full of skyscrapers before (London City and Canary Wharf don’t count) so I took many photos! I was also impressed by the fact that all the interesting places to visit were pretty much close to each other, so in 3 days I visited most of them!
So let’s get to what’s worth doing in Chicago!
Get up to Willis Tower and/or The Hancock Observatory. In the beginning I was reluctant to go up (my first time going that high), but in the end it was totally worth it, as they provide an incredible 360 degrees view of Chicago!
View Chicago’s skyline from the Aquarium (see photo above) or the Navy Pier. If you like to see fish swimming around or are travelling with kids, visit the Aquarium as well!
Take lots of pictures of The Cloud Gate by Anish Kapoor in Millennium Park (I took selfies there, before they were even a thing!)
Walk around the Financial District, enjoy the different architectural styles (skyscraper architecture started off from Chicago in case you didn’t know) and find works of art like those sculptures by Picasso and Miro.
Visit the Art Institute of Chicago which is famous for its collections of Impressionist, Post-Impressionist, and American art
Walk around Chicago’s Theater District to catch a glimpse of those vintage looking marquees!
Visit the Zoo in the Northern part of the city. Definitely a family friendly activity!
Walk along North Michigan Avenue a.k.a. The Magnificent Mile and window shop!
Walk by the Chicago River along Upper Wacker Drive (opposite the Wringley building and up to the Willis Tower). It has some of the best views of skyscrapers.
Eat at The Cheesecake Factory in the Hancock building. It was my first time at Cheesecake Factory and I ate so much that I felt stuffed for the next 12 hours! Also loved the art nouveau interiors as well!
I'm Anna and this is my lifestyle and travel blog! 
Looks like you hit the biggest “must-see” places! Hope you had a good time!!!
Thank you for sharing this with me! It was so helpful.