Let me tell you about my favourite city in the whole world: Chicago

Falling in love with a place is always special. Sometimes it’s a slow burner, and it takes several trips to realise that you’re actually very fond of it. Other times, you love can gradually develop as you see more and more of a place. And, quite rarely, you can love a place from the second you step foot off the plane/train/automobile.

Chicago is one of those mythical cities that fall into the last category.

I can’t pinpoint exactly what it is about this cosmopolitan city that makes me love it so much. Maybe it’s the pizza that resembles a pie, the winding river that cuts a path through the skyscrapers, or the above-ground subway line that is how I imagined New York City to be. Or, more likely, it’s a combination of factors. Read on to find out why I think you should love it too.


The bean! Officially named ‘Cloud Gate’, this is the reflective sculpture that pretty much everyone has to take a selfie with. It’s popular for a reason, though. Seeing yourself perfectly reflected in every surface is pretty cool, and it’s in the beautiful Millennium Park. As we wandered past the beautifully designed stage, some opera singers with a full orchestra were rehearsing for a concert. The haunting music against the beautiful backdrop was so surreal.


The Navy Pier. This gets the prestigious title of being the most popular attraction in Chicago. With fun fairs, an IMAX cinema, museums, restaurants (including a good food court) and bars, you could easily spend the best part of a day here. If I visit again, I’m definitely going to pay for one of the firework boat cruises and see explosions in the sky against the cityscape background.

Michigan Avenue. If you want shopping, you’ve come to the right place. Part of this street is dubbed the ‘magnificent mile’, and the shops really do run for that long. Once you’re all shopped out, there are lots of quieter and cute side streets to explore, filled with Ferraris.

Top of the Willis Tower. Once the tallest building in the USA, we caught the lift to the viewing platform at the top of the building. The highlight were the glass boxes that hang out over the edge of the building. The vertigo was intense but it was so much fun.




  • Explore some of the districts. We stayed at the IHSP hostel in Wicker Park and the area had a great atmosphere. It was cultural, young, and some say it is where the first hipsters came into being. I’ll let you decide if that’s true for yourself!
  • Take some time out of sightseeing in favour of a relaxing walk down by Lake Michigan. I really enjoyed strolling along the shore, taking photos and people watching.
  • See some sports. We were in Chicago during baseball season, so we went to see the Chicago White Sox play against the New York Yankees at U.S. Cellular Field. I barely know the rules of the sport, but the atmosphere was really exciting and we felt quintessentially American with our hot dogs and sodas.



Chicago is famous worldwide for it’s pizza, so we had to try some. We ordered some from the really popular take-out down the road from our hostel, and ate it on our private rooftop balcony, overlooking the city skyline as the sun was setting. Maybe it was the location and atmosphere that keeps my memories of that meal so happy, but I’m sure the pizza also had something to do with it. About two inches thick, these pizzas looked like a thin pie. They have the cheese on the bottom and ketchup on the top, a Chicago staple, and it really works. I could barely manage two slices, even though I desperately wanted more. We got our proper Chicago pizza from Lou Malnatis.


IMG_1059 DSCF0190 DSCF0183


Have you ever been to Chicago? Tell me about your favourite parts! Would you like to visit in the future? 

lisamae signoff


  1. May 26, 2016 / 7:49 am

    New York was that place for me! I can’t wait to go back and I can’t wait to take Jacob! I’ve always wanted to go Chicago (ever since I does watched ER) and because I loved New York so much I’ve been told I’ll love Chicago. Xxx

    • Lisa Mae
      May 27, 2016 / 7:45 pm

      Definitely! It’s like a more relaxed version of New York. And as much as I loved NYC, that easy-going atmosphere was what it lacked for me. Thanks for stopping by!