Travel Blog: Chicago


Prohibition and the 1920s in general is my favourite historical era, Chicago was a key city during this time as it was the home of notorious gangster Al Capone. As a result of this interest in the era I had read a lot about the city and always thought of it as a place that I would eventually like to see but honestly didn’t think I would get around to it during my year abroad though I’m not sure why. That is, of course, until Valentina messaged me on Twitter. I had never spoken to her before and yet she invited me to the city, offering to show me around and saying that I could stay with her. Naturally, I was taken aback by such an offer but I don’t say no to a trip. We got to talking and a couple months later we met up in Chicago.

How I travelled:

  • National Train
    Honestly this deserves its own section. The trains here are awesome!!! They are SO big, in all aspects. They are so incredibly tall, you need to go up a few steps to get on it and when inside they are very spacious. I travelled in economy class and the chairs were huge, they stretched back a lot and were really comfortable. First class must therefore no doubt resemble a hotel. The trains are genuinely like the Polar Express. There’s a conductor who’s uniform is exactly like in the movie who goes around with a hole puncher. Magical. The only downside was that the lights were on all night and it was really cold so it was hard to sleep. Next time I’m definitely taking a blanket and an eye mask.

All aboard the Polar Express!!
What I did:

  • Union Station
    This was where my train arrived which also happened to be where the scene in The Untouchables was filmed. Very exciting for me, again Prohibition is my fav time ever.

    The steps where the baby stroller rolled down
  • Al Capone’s House
    In keeping with the history theme of my trip we went to Al Capone’s house. It’s located in a quiet neighbourhood and doesn’t really look like anything special, I suppose it was worth a lot more 100 years ago. I’m not sure if anyone currently lives in it as I found some articles dating as recent as 2016 that the city was struggling to sell the house and the price was falling, as low as $200,000. The house itself was pretty underwhelming but it was still pretty surreal to see the home of someone who I’ve read about so extensively and watched so many documentaries on.
  • Trip to University of Illinois
    Valentina’s friend invited us to go for a night out so we drove for a couple of hours and finally arrived. It was really fun because the bars there had entry age of 19 which meant that I was finally able to go out out. That night we stayed at a frat house and the next day took a quick tour of the campus which was absolutely gorgeous. It was exactly what I had imagined American universities would be like. Greek life, meaning Frats and Sororities, are huge there so driving around there were so many houses with Greek letters on them and they were absolutely huge. The one I stayed in was valued at $15 million, it had an elevator inside and a kitchen with a cook. On Saturday morning when we drove around all we could see were pledges cleaning the mess from the night before which was pretty funny. The entire campus felt straight out of any American movie. Admittedly, it was all I wanted in a university here so was a little heartbreaking to see it and not be able to attend it as the one where I’m currently at isn’t like that at all. UoI was actually my fifth choice, one bellow Buffalo, which I hadn’t even realised until I checked my emails out of curiosity later on.

    An actual BAR
  • The Bean
    We went back to Chicago, got dressed and went around the city. We walked around in the city area and I loved it, there were tall buildings and busy streets everywhere. Eventually we made it to the Bean, one of Chicago’s most recognisable tourist attractions. It reflects the city’s skyline and obviously yourself if you stand in front of it.
  • Navy Pier
    It took us about half an hour to walk there from the Bean but it was a nice day and was definitely worth it. This is another popular tourist attraction in Chicago where it was particularly windy. We mostly ate here and later on took in the beautiful sky line, lights and illuminated fountains that were around.


  • London Tower
    This is a hotel with a roof top bar. The view was spectacular. Honestly, I was pretty surprised I was able to actually go because first of all I’m underage (20) and secondly, the place is super fancy and I was dressed like an absolute tourist. Regardless, after a twenty minute wait in line we managed to go up. We just took pictures and hung out for a while because those drinks were not affordable, with a quick glimpse at the menu we saw nothing cheaper than $600. After this we went home and fell asleep immediately after a long day of walking.

    Rooftop living
  • Willis Tower
    On Sunday I took on Chi-City alone as Valentina had homework to do. It was pretty cool wandering around with only Google Maps to help me and occasionally the help of strangers. Willis Tower, formerly known as Sears Tower, was built in 1970 and took three years to complete. It was the tallest building in the world for 25 years, now it’s the second tallest in the US and 16th in the world. You can see the entire city from the top and there are glass viewing decks where you can see even more. I didn’t really think about how scary it would be to walk on that ledge, I just did but when I got there I felt so dizzy. That’s the moment you realise exactly how high 108 floors really is. This was definitely the highlight of the visit. Unfortunately, I was alone so I didn’t get any good pictures because strangers suck and they all came out dark. I definitely recommend going with some friends who are somewhat competent with a camera.

    I caved and bought the pic they took
  • Chicago Theatre
    I really just went for the picture with the sign. Have you really bean to Chicago without a picture here though? The theatre is located in the city centre so it’s surrounded by high street shops which was nice to just walk around. I walked from the tower to the theatre, it was only a 15 minute walk but it took me like 45 because I got lost. The roads in America are usually straight because they learnt from European industrialisation and didn’t build like a maze. I thought because of this I wouldn’t ever get lost but I don’t really know what happened. Anyway I survived.

    Solid pic because I asked a woman
  • Chicago History Musuem
    Aka heaven for a history student. There were so many displays, I had to rush at the end to see them all because I only had three hours to read everything. I absolutely loved the museum, my favourite part was the Jazz display that had the most famous Chicago jazz artists in a room set out like a bar. There was a wide variety of history, ranging from that of the city dating back to the settlement of Europeans and their encounters with the natives, to history of the entire country. There was a section about the internment of Japanese Americans after Pearl Harbour and how they were essentially imprisoned by the government under no real pretence and kept in really inhumane conditions. It was really interesting, especially to learn about times and events I’d not heard of. The only thing that was a little disappointing was that I didn’t get to see much that was Prohibition related. I had looked for museums dedicated to that and couldn’t find any, I thought there would be a big section on it here but there was just one small wall. Still, I learnt a lot.

    Women’s suffrage exhibition
    The only Prohibition/gang related exhibition
    The Chicago flag and the meaning of the stars
    Jazz exhibition playing music & set up like a bar

What I ate:

  • Deep Dish Pizza @ Giordano’s
    Wow. What an experience. What a pizza. My life is forever changed. I got Chicago Style deep dish pizza which contained pepperoni, mushrooms, green peppers, onions and sooooo much cheese. It was absolutely delicious!! So much better than New York pizza, which has offended many people but to be honest I am right on this. Chicago wins, there is no competition. NY pizza was big and greasy, this was also big but super tasty rather than just filling. I’ll take deep dish any day.

    What a BEAUTY
    Look at the DEPTH
    Eat (Chicago) Pizza!
  • Bubba Gump Shrimp Co
    The wait time for Giordano’s was around an hour so we got appetisers here which was across the hall inside the pier. It’s a Forrest Gump themed restaurant. I’ve not watched the film so didn’t get the reference but the inside is cute and the food, from what I can tell, is good. We had shrimp mac and cheese which was delicious.

    My dinner date
  • Cupcakes
    There’s lots of little adorable places to go into, filled with fairy lights selling over priced pastries but it’s worth it for a little break.
  • Mexican Food at Pepe’s
    My first time having authentic Mexican food as opposed to a westernised chain. The portions are huge and so good.

    Valentina’s plate was nicer tbh
  • Italian beef with Mozzarella cheese from Al’s
    I don’t have a picture of this because it was gross. It was Valentina’s recommendation but it was so bad I didn’t eat it. It’s basically a bun and beef inside which just doesn’t make much sense to me, also the bread is wet because you can get it dipped in something. That just made it worse.

What I’d do with more time:

  • Jazz Bar & Saloon
    I have to be 21 for both of these things unfortunately. There’s a Saloon in Chicago which apparently is a barbershop during the day and bar at night, there’s a security that you have to whisper a password to and it might get “raided” by the cops. Given my love for the era, I was really upset that I was underage when I went. Also Chicago has really good Jazz so if I ever visit again I have to check it out.


That concludes my time in the Windy City (a nickname it has not only because of its wind but because of its politicians full of “hot air”). I had a wonderful weekend in such a beautiful city. Shout out to my new friend Valentina for showing me around, hope to see you again some time soon.



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