Today was an exciting day: Chicago! The third largest city in the United States, topped only by New York City and Los Angeles. We weren’t headed straight for Chicago though, first we stopped in Gary, Indiana to do some DoorDash. Well, let me tell you, we were not prepared for how run down this town would be. Gary was a town primarily employed in the local steel industry, so when that industry shrunk due to the increase in foreign steel imports, it threw the town into some pretty bad times.
There’s barely any lane lines on the road, so you kind of have to guess where you’re going, all the while dodging tire-sized potholes that will be sure to ruin your day. There’s also a ton of completely abandoned and literally falling apart buildings (missing walls, busted windows, etc.) covering vast areas of the city. We did some research, and apparently the average home price here is $86,000 USD. Coming from somewhere that has an average price of around $600,000 USD, that’s absolutely wild to me, though it does make sense, location is everything.
After a bit of driving around Gary, we decided to go to the East Chicago train station, park, and take the train into Chicago itself. Parking was free, but because it was a bit of a sketchy area we decided to hide basically everything, including batteries, the CarPlay unit, and the majority of our blankets and pillows. It took a bit of work, but the peace of mind was worth it. We walked inside and bought our tickets at the ticket machine, $7 each from East Chicago to Van Buren Street. Because we’d arrived just after a train had left, we had to wait an hour for the next one, which was fine because there was a shelter to hide from the wind in.
The train arrived a few minutes late, thought I wasn’t expecting on time performance from an American train. We hopped on board, and while not the most comfortable train, it was fine for being a commuter line. There was even a USB-C and USB-A port on the back of the seat that worked. Unfortunately, I couldn’t really see out the side of the train because the windows had those black dots all over them from when an advertisement is plastered on the outside of the window, like on a bus. The train was also really warm and muggy, and it felt like they didn’t have any outside air coming in.
After 45 minutes we arrived in Chicago and walked another 10 minutes to the waterfront of Lake Michigan, where we dipped our hands in the lake just to say we’ve done it. Once that was done, we walked a further 15 minutes through a very nice park to… The Bean! It’s actually called Cloud Gate, but it’s a massive bean and I think “The Bean” is a better name for it, and what everyone calls it. It was super, super busy so we weren’t going to get a good photo with it, but we were able to get photos of it, and walk underneath it to the other side. Apparently some people lick it, but Kyle wouldn’t let me do that.
From there we decided we wanted to try the legendary Chicago Deep Dish pizza, and looked for the best place in Chicago according to others. We found “Pizzeria Uno”, which was apparently one of the first places to do it, and put it into our navigation. We had the option of taking the subway, but it actually would have ended up taking longer than if we’d walked, so we decided to just walk.
Our walk took about 25 minutes, and brought us past the Trump Tower, which I’d forgotten was in Chicago. It’s a very tall building, one of the tallest I could see, and is by all means actually a very nice looking building, were it not for the massive “Trump” writing on it. Our walk also took us across the river, where we saw the river walk and vowed to go back later and walk along it.
We arrived at the pizzeria and saw quite a long line to get in, so we were a little worried we’d have to wait a long time. Someone walked out after talking to the hostess, so I asked him if he knew how long the wait was. He said you could place your pizza order, then in 30-40 minutes you come back, sit, and order the rest of your stuff. We decided that was okay, so we headed to get our order in. It turns out that the large line of people was actually all one group, and the reason they took so long to get in is because it’s really hard to find seating for 12 people in a tiny restaurant like this. We, as a party of two, were seated immediately, and while we still had a 30-40 minute wait for pizza, we could at least do it with drinks and wifi in a warm restaurant.
As we were waiting for our food, someone came up to us with a camera and asked if we wanted a photo together. Weary of how much it might cost, I asked explicitly if it was free, and she said that they do a complimentary photo, and then you can pay for extra photos. I, still wanting to be explicit about not paying, said “Let’s do the complimentary one” and we got our photo taken. She then left, and I presumed she’d come back later with the printed photo.
We finally got our pizza, which was pretty small all things considered, but it’s a lot thicker than normal pizza so it kind of makes sense. The waiter said it was very hot, so she would cut the first slices for us, and she cut it into four pieces and gave us each one. After waiting a bit for it to cool down, we dove in. This might be a controversial statement, but I think I much prefer classic pizza over deep dish pizza. The first few bites were good, It was thick with sauce, toppings, and dough, had a great mixture between them, and was very tasty. After that, it got a little less tasty because it strangely had a pretty overwhelming taste of red wine the closer to the crust I got. It ran out of toppings, and was mostly just sauce with the aforementioned wine taste. I would definitely try it again at another restaurant though, as I don’t want to rule out the whole dish based on one experience. We also got our photo back while we were eating, in which Kyle looks a little scary.
After eating, we walked around a bit in search of a bathroom, which we found in a pretty fancy hotel. The door to the bathroom needed a keycard, but luckily there was a few people walking in as I walked up and so I was able to follow after them. The key to doing anything in a hotel you’re not staying at is to just act like you’re supposed to be there. Don’t attract attention and just walk with purpose.
We then walked to the river walk, where we got some nice photos and then walked along the river towards the lake. We were heading towards Navy Pier, a commercial strip on a pier with good views of the city, restaurants, shops, and a giant ferris wheel. We weren’t really in the mood to eat again, nor do any shopping, so we were really just going to get some nice photos of the city and to experience the area.
Once we got our photos, we realized that we could get a train back to the car if we left right away. The train left in 17 minutes, and the walk was 17 minutes. It was tight, but we decided to try and give it a go. We hustled our way through the city back towards the bean on our way to Millennium Station. On the way, we noticed there was an abnormal number of police hanging around, like over 100 on just the few blocks we’d walked so far. We decided to ask one of them what was going on, and they told us that there was a TikTok trend going on right now where about 100 teenagers planned to rush the area and cause havoc, and the police were there to try and dissuade them from doing that. I feel like an old person when I say this, but this is some weird young people stuff, we never did this kind of thing when we were teenagers.
Despite that minute of conversation setting us back a minute or so, we were still on track to make it to the train station ahead of schedule, hopefully enough time to find the train and buy our tickets. We finally arrived at the entrance to the station, or at least we thought we did. Google Maps was apparently completely wrong, and the station entrance was over two blocks away! We obviously missed the train, and so we decided to go to a nearby Swissotel so Kyle could use their bathroom. While there, I noticed they had sitting space in the lobby and wifi that worked, so we figured we’d sit there for a half hour or so until it was time to walk to the train.
After our hotel break, we started our walk to the actual station entrance. While crossing a crosswalk at a stop sign, a turning car honked at me, which, being petty, I took as a sign to stop walking and slowly turn to look at him for a few seconds before continuing. If you honk at me for legally crossing the road, I will make you wait longer. This is something my mum (hi mum) would say is a bad idea because she’s worried they’ll shoot me or something, but I think it’s funny.
We got to the train station and were a bit lost. We found a lot of signs for the Metra trains (the commuter rail for the Chicago metro area), but we couldn’t find signs for the South Shore line, the one we needed. We came across a staff member who seemed to be packing up for the day and we asked them, and she very nicely directed us to the right area. The ticket machines are interesting, because even though they’re purpose built they still suck. They’re slow, have a bad UI, and are physically massive. Also, our ticket machine was in Spanish! We remembered enough from the first time we got tickets to be able to make it through the prompts despite the language barrier though.
We got our tickets, boarded the train, and a few minutes later we were on our way. It was another 45 minutes back to the East Chicago station, and this time the train was much more full (though not packed), and didn’t have outlets in the seats. The wifi also didn’t work, which was a standout feature of the ride to the city where it did work pretty well. We got back to the car with no issues, except that we had to unpack everything that we’d hidden when we left, which took a little bit.
After unpacking, we drove to South Bend, Indiana to do some DoorDash, which we did until around 1:30am. It was a bit later than we’d hoped, since it was still an hours drive to the rest area, but we got there around 2:45am and very quickly fell asleep.