It was 2013 and I’d unexpectedly found myself in Chicago after accepting a summer job in Wisconsin. I checked-in to HI (Hostelling International) slap bang in the centre of what would soon be known as- my favourite city in the world!

It was a large hostel. In fact, large would be an understatement. It was the biggest hostel i’d ever stayed in anywhere in the world and that’s saying something for a backpacker! How would I ever make any friends in a place so large?

It was early morning and i’d heard about an ‘architecture walking tour’ the hostel were offering around Chicago for free. In a city filled with amazing architecture I figured that this would be a good opportunity to learn about the place… So I jumped on the tour and joined the dozen for the walk.

It was pretty dull. I still remember to this day the feeling of boredom. The old man leading the tour claimed to be an expert and proceeded to tell us about Chicago being home to the tallest skyscraper in the USA. I looked at him with confusion. I’d just flown to Chicago from New York and spent a day at the World Trade Museum. I’d learnt first hand that One World Trade Centre now took the crown for the USA’s tallest skyscraper. I didn’t say anything, I let him continue.

Before long, an American stepped in and questioned this. “I thought the tallest skyscraper was in New York? The Freedom Tower.” The tour guide continued to shut this down arguing this wasn’t true.

As we continued to walk, I pulled aside the American and told him he was right. It is the tallest building. This guy was smart, intuitive and questioned things he believed to not be correct. I later learnt his name was Rob and he was from Cincinnati. I had no idea that a silly comment about a skyscraper would put a person in my life for the next decade and more.

We spent the weekend hanging out with others at the hostel and enjoying Chicago. It was the start of a friendship and a connection with a fellow traveller and blogger. He was writing about his road to turning 30 and all the things he wanted to achieve before he hit this milestone. I was 23 at the time and I remember thinking, what an awesome idea. I’m goal orientated and so was he. I followed his blog and journey religiously and he followed my blog as I continued to travel and work around the States. We had a mutual passion for adventure.

After we said goodbye and began our onward journey’s I knew we would keep in touch. What I didn’t realise was I would see him sooner than I thought.

3 years later, i’m returning to the States to visit NYC for NYE. I tried to convince Rob to join me but I knew he had a passion for Chicago at NYE. After my 5 days in New York I was lucky enough to land a layover in Chicago on my way back to London. If you have ever looked at a map of the USA you’ll know that this route makes zero sense! But I didn’t argue. I got on that flight and with less than a 24 hour layover I fully made the most of that stop!

After checking in to the familiar HI again, I ventured out through the snow and met up with Rob. He’d travelled over from Cincinnati again and I really appreciated him crossing states to meet up with me for such a short time! We even exchanged chocolate where we both gave the best our country had to offer. I couldn’t resist the need to give him a Terry’s Chocolate Orange because seriously America does not know good chocolate!!

We walked the streets and Rob watched as I was amazed by the deepest snow i’d ever seen in my life! He had planned to show me what real pizza was. The deep dish was invented in Chicago and he knew exactly where we should go. So we headed for Pizzeria Uno. I remember this visit like it was yesterday. This is without a doubt, the best experience I’ve ever had eating pizza! It was literally like eating a pie crust.. It was that thick!

Rob towered over me in height. It wasn’t hard since I am only 5 foot! But i’ll always remember him taking away more of his pizza than I did. I seriously stuffed my face! He warned me to get the smallest size and he definitely wasn’t wrong! I think it could have continued to feed me for days haha. One day I hope to revisit here and share the experience of real pizza with more friends. Have you really ever had pizza if you haven’t been to Uno’s!?

It was only one night in Chicago but it exists in my memory bank for so many good reasons. I remember feeling so appreciative that somebody took the time out of their lives to meet with me and introduce me to their home country. I wish I could have visited Cincinnati and one day I will. I don’t doubt that.

Rob was one of the kindest people I ever met and probably the most memorable person from all my travels. Even to this day, he’s the one I kept in touch with the most despite backpacking for years. Rob made the most of every opportunity to travel and I watched as he went from visiting Chicago over and over, to hopping down to New Orleans and Miami, across to Boston and Philly and he even made it to New York too! I know he always wanted to visit the UK and i’m glad I was able to chat with him about all the strange things we do over here. The royal family and UK politics were definitely a hot topic! He was so inquisitive and curious to learn about other cultures. Rob was taken too soon and like so many others he didn’t get long enough on this Earth. But he lived a fulfilling life and i’m so proud of all the things he achieved.

I will miss you Rob and since I have been craving a visit to the States since my last journey to Chicago in 2017, well I think now might be a good time to revisit in your honour. What do you say?

To Rob, thank you for being you and may you rest in peace.

“As I have learned, life is incredibly short and you never ever know what difficulties life will throw at you….YOU MUST NEVER take anything for granted or assured, because you never know when it is all gone. This year, I want that to be your mission in life. Live life as if you had nothing and had to earn it all back. Never take anything and expect it to be back later. Take everything as it is and never question how lucky you are to experience it.” ~ Rob, NYE 2025