Chicago River at night

Once again, I’m writing up a blog post about my trip nearly a month after the fact. Do not think me lazy reader. You see I have a whole process where first I must record everything manually in my travel journal and also prune my photographs into a pleasant album for ease of recollection. It is only the most delightful parts that make it into these posts: the other bits and pieces are for me alone.

Let’s return to the completion of my cross-continental loop. For my return journey to Vancouver, I first flew to Chicago (as rail would have been too much of a pain) and spend several enjoyable days there. Here are the highlights.


Chicago’s “L” is apparently the 3rd largest in terms of ridership in the USA (after NYC and DC), but I wouldn’t have guessed it if I hadn’t been told. The Blue Line from O’Hare airport to downtown was poorly signed so you didn’t know what train to get on or when it was leaving. Despite the train being cleaned while we waited, there was still plenty of trash on it by the time we left. Halfway through we had to transfer to a shuttle bus because half the stations were under construction on the weekend. This led to a great deal of chaos and the trip taking 45 minutes longer than it should have.

Also, all the stations smelled of urine and were generally dark and unpleasant. NYC seemed clean and pristine in comparison. I just ended up walking everywhere in the city until I had to leave for the train station.


90% of the reason to go to Chicago is just to marvel at all the architecture on the Magnificent Mile. You crane your neck to see the skyscraper tops in the day, and you go back at night to see them glow in the evening.

My favourite has to be Marina City, which I’d heard about before visiting and used to orient myself while finding my hostel. It’s one of the earliest attempts to build a large mixed use complex in North America. You can take your elevator down to your car or your boat in the marina! The complex includes a movie theater, shops, and all that good stuff. The video below gives a good overview of the building:

Characters at the Hostel

I lucked out in that I ran into two pleasant people in my hostel dorm: W_ and A_. W_ was a former ballet dancer who now works in hospital administration. His family was from Puerto Rico, he described himself as LGBT+everything, and lived in Anchorage, Alaska, which was quite the combination. He also claimed to be an introvert, but he struck up conversations with every single person we met—even in the elevator—and the fact that I managed to go 8 hours without having a conversation with anyone the next day was a shock to him.

When we were unpacking our stuff, he joked that he was in danger of falling out out of the top bunk. This turned out to not be a joke as after partying till around 2am the first night, he fell out and hit the floor with a horrible thud. I was worried he’d hurt himself, but the muscle relaxant properties of alcohol kept him whole. In the morning, we found that he had somehow knocked off a runner from my bottom bunk in the process. He had no memory of this, but said it did explain the bruise on his leg.

And then he did it again the next night! We really should have switched.

A_ was an engineer and much quieter. He was taking photographs of his trip on a film camera. He asked if he could take pictures of us to add to his collection. W_ and I agreed, but W_ insisted he choose the background. A_ agreed. W_ chose the floor of the coffee shop we were sitting in. The lighting wasn’t the greatest, but it was quite funny.

Museum Fun

The two museums to go to in Chicago are the Art Institute and the Field Museum. Go to one for the paintings and the other for the dinosaur exhibits. I maybe got through 50-75% of both despite spending close to 4 hours in the Field. My favourite parts were the accidental discovery of a painting of Beatrice Portinari that I knew about because of some novel research, and the majestic Tyrannosaurus Sue.

Final Thoughts

Chicago is a great place to visit for about four days or so. The architecture is amazing, the riverside park area is green and has beaches, and it’s easy to walk around the downtown core. However, I’m not sure I’d want to spend longer. The downtown was clearly planned in the 19th century (all the parks go over here and all the office buildings go here), and there aren’t many interesting small shops or restaurants, but there were a lot of Starbucks and other chain establishments. I had the impression that the skyscrapers just squeezed out all the interesting small places.

Finally, outside of the downtown core the city was a car sewer, and I think the only meal worth mentioning was the one I had at a Rick Bayless Happy Hour. Chicago definitely could use some more Marina Cities.

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