In 2024 I was sitting at my laptop watching YouTube videos and saw one about the Pinball Expo in Chicago. It was only a day old and was covering the first day of the expo. I checked flights and headed there the next day with my friend Michael to catch the final two days.
On the last day of the convention one of Michael’s friends picked us up to show us around the city. I had no real impression of Chicago prior to this. I had been a few times in the past, but only in the winter which didn’t lend itself towards exploring the city. The way he talked about Chicago was how I talk about Las Vegas. He loved his city and was excited to tell us about all of the hidden sides to it that we weren’t aware of.
He took us to Pequod’s pizza. I love pizza, but am generally not a huge deep dish fan. Pequod’s was amazing. I had never had deep dish that good before, and I literally thought about the pizza about five times a week for the next six months.
After talking about this pizza for half a year, my wife and I finally found some time to go to the city together on a one day layover before another trip. We ubered to Pequod’s (it was good, but not quite as good as I remembered), walked around the city and went to an amazing pinball arcade.
Chicago is a strange city. It’s the third biggest city in the US and no one I know has ever mentioned it. Everyone talks about SF, LA, New York, Miami, Austin, etc… but none of my friends ever seem to go to Chicago. And yet… I think it’s a lot nicer than those cities. The river runs through downtown, with bridges every block or so. The skyline is incredible. The food is great. It’s in an interesting geographic location, not that far from the east or west coast, with great flights to Europe and Asia.
And… the real estate is absurdly cheap. If there’s one thing I can’t resist, it’s real estate that is underpriced. I wasn’t sure if I’d actually buy a place there, but either way my wife and I wanted to spend more time so we booked a week-long trip and contacted a real estate agent.
We had a great week in Chicago. The Art Institute is one of the best museums I’ve been to, and the only one that elicited an audible “oh my god”, by both me and my friend as we walked into the Monet room. Qiao Lin was the best hotpot I’ve ever had (and I spend a lot of time in China), and Au Cheval is perhaps tied for best burger. We saw the Chicago Symphony Orchestra at Ravinia Festival, which is an amazing outdoor symphony hall. The architecture was, to me, more interesting than that of any other US city, especially when seen from the river on an architectural tour. I even met up with a reader (hi Noah!) at Living Water, a surprisingly good tea house that appears to be a boba place when you look it up online.
All of our condo showings were at the end of the week. The night before I started doing the math on it and realized that it doesn’t actually make sense to buy a place there. The taxes and HOA fees are so high that financially it makes a lot more sense to go visit several times a year and stay in a nice hotel. I didn’t want to cancel the showings, but I went into them thinking, “Too bad… I wish the numbers made more sense so that I could actually buy a place in good conscience.” My wife was campaigning for just staying in hotels and said if I wanted to buy an apartment I could do it by myself.
The first three units were okay. If I were actually moving to Chicago I’d be happy in any of them, but in each case I had to admit that staying at a hotel would probably be just as good, if not better. The fourth was better and I felt like maybe I could convince myself it would be better than a hotel, but I knew I was stretching.
The last was a wildcard. The images online made it look terrible, but the location was amazing and so was the price. As soon as we walked in, we saw something that you couldn’t see from the listing— the view. My wife, previously quite uninterested in buying, turned to me and said, “I think we should buy this one together”. I went out on the balcony and realized there was no way I could avoid buying the condo. It was just too good, and with the view it was much better than any hotel room we could get.
As we returned the keys to the front desk I took a glance at the visitor log. Other units for sale in the building had maybe one visitor, but this one had five. We put in an offer immediately, and were told that there was a competing offer. In my estimation the unit was actually worth about 20-25% more than the list price, so I was worried that we were about to get into a bidding war. I don’t quite know how he pulled it off, but our realtor managed to get it for us for under asking. I looked up historic prices in the building and couldn’t find a single one of this size that went for this price.
The next day I went to do the inspection myself. At first glance many of the systems like the fridge and AC seemed to be broken, but it turned out that they actually all worked fine. I was totally prepared for a major renovation, but it turned out it only needed cosmetic fixes. It was being sold by a trustee of an estate, who I believe never had it inspected or even cleaned, so my theory is that the seller and any other buyer assumed it was much worse than it was.
We closed a few days ago and in a couple days I’ll go to the condo for the first time and start getting to work.
The best part of having properties all around the world is getting to know places in a much deeper way than I could if I just visited. I went to the island twice in the past month and was reflecting on what a unique privilege it is to get to know the community there. When we arrived our neighbors gave us a basket of homemade baked goods and vegetables from their garden. When we went to dinner the waitresses remembered my name and asked what projects we were doing this trip. The lady at the hardware store told me about her trip to Vegas because she knows I live there.
I’m really looking forward to getting to know Chicago. It feels like a massively underrated city with a ton to offer, and its strengths and weaknesses complement Vegas perfectly. Vegas’ biggest weakness is the lack of fine arts, but Chicago has that in spades. It’s freezing in Chicago in the winter, but Vegas has great winter weather. Vegas has a brand new powerhouse hockey team, Chicago has one of the original six teams and is rebuilding with one of the hottest rookies in almost a decade. Vegas has a very small walkable downtown, Chicago goes on forever. It’s also a ~3.5 hour flight between the two cities, which is just under my threshold of long flights. If I look a month out, round trip flights are mostly under $100, with several days in the $39-50 range.
I know I’ve said it before… but I think this must be my last real estate purchase. Between Hawaii, Vegas, Chicago, Budapest, Tokyo, and the island… I’m going to need longer years.
Any Chicago recommendations? Do you live in Chicago? I may do a meetup there at some point.
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Photo is the skyline from the First Lady architectural tour. It’s rare that I’d say a tourist thing is a must-do, but that tour definitely is.
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