Cape Horn Illustration



Phil Thompson uses illustrations to document the underrated parts of Chicago that he wants to celebrate. He then sells these works of glorification at his online website. In his own words — “When I get obsessed with things, I make art for people who are also obsessed with those things.”


Cape Horn Illustration started in 2013.


The home studio is located in Ravenswood.

Why Cape Horn Illustration?


I’m face to face with Vincent, a good dog. His owner, the illustrator Phil Thompson, makes tea in the other room. Vincent doesn’t lick as it’s not in his nature, but he presses farther and farther into my space until I have to lean back over the couch in order to avoid his curious nose. Vincent just wants to take in the fine details of this world.

Thompson runs his business, Cape Horn Illustration, from home. Vincent, a black and white Morkie poo, runs around this home. Once, Vincent charged through the screen door right next to Thompson’s drawing desk. The hole remains.

With Cape Horn Illustration, Thompson has spent more than half-a-decade highlighting his favorite parts of Chicago with dogged precision. A spatially accurate map of the Chicago Lakefront took over a year. His drawings of homes all across the city include tiny details that likely would have gotten lost in a photograph taken by a camera phone. In a way, his drawings are the most accurate way he can record the city he loves.

After Thompson returned with two cups of tea to join me and Vincent on his L-shaped couch, we talked about this.

“A drawn piece has a certain quality to it, where you can give it kind of a look to convey an additional layer of information,” Thompson said. “So to me, when I want to create one of these print series celebrating the home styles, one thing I’m going for is trying to make it have this timeless look. Like iconic. Which is how I see these home styles.”

Read on for an edited and condensed version of our conversation…



Your Chicago Lakefront map took you a year to complete and then didn’t quite hit the market as you expected. In retrospect, what happened?

Thompson: The Lakefront map was the second big project that I did. And yeah, that one, you know, it just didn’t find its audience, but since then it has.

One thing I realized is, OK, it might not find that niche audience where people see it and they make an immediate connection between the piece and their own identity. But it’s also about where it’s presented, like the context. It does much better in shows when people can get up close to it. You can see it and really get involved with it.

Then when people go to the website and just see it on a screen…

You have to zoom and it’s truncated.

Yeah. So that’s something that I learned and it’s just been part of the whole journey.

Can you talk about, just as an artist in spending a year on something, how it felt when it was done and then it didn’t quite pay off as you expected at first.

It’s just a huge disappointment. I mean, you have an expectation in your mind that it’s going to do such and such, like, oh, if I posted it on Reddit, people are going to just go crazy. And then you go back to Reddit, click refresh, click refresh again. Keep going back and that’s this deflated feeling that’s a day long and then a week long and then you just don’t get that kind of traction that you were hoping for. But I think, since then, I’ve just learned that… it happens.

Just because it doesn’t do well right out of the gate, doesn’t mean that it won’t eventually find some other life.

It has its own value anyway.

That’s the benefit of experience. But at that time that was really the second big piece that I put out. So I didn’t have any context to put it in, it was just one of two data points. It was kind of like, well, this sucks. I’m never going to be able to make um…

Make the leap?

Yeah, yeah exactly.

Just with my own writing, there have definitely been projects where it’s taken a long time, then I put it online and the view counts are just not there. And it’s like, well fuck, I guess that’s that.

Yeah. But I think that’s another thing about it is you kind of build that in. It’s like, well I’ll put this up with no expectations and then maybe be pleasantly surprised when there are responses.


Why are you passionate enough about Chicago to be chronicling this city with your art?

I think the biggest thing to me was that I was just so blown away by the neighborhood architecture and the fact that so many streets have these themes running through the homes and the buildings. But I felt it wasn’t really celebrated a lot. That kind of motivated me to do something about it.

You have these architects that were just using the city as their canvas and figuring out an organic homegrown style that was then incorporated into a lot of the built environment and the city.


[Vincent has started burrowing into the couch cushion next to me]

I think he’s trying to dig a hole.

[After we’ve calmed Vincent down] You see a lot of celebration of the very unique buildings that we have like the skyscrapers. But I just didn’t feel like the neighborhood architecture was really celebrated enough. So to me, there’s a big disconnect between my lived experience — just walking around and gawking at everything. I felt this big gap. I want to see people celebrating a bungalow because it’s a fricking awesome home style.


This isn’t exactly art related, but I’m also a runner and since you do interpretations of marathon maps…

Vincent, Vincent. What’re you doing? What’s down there?

[Vincent has started scratching into the couch cushion again.]

I hid dog food in there while you were in the other room.

[Thompson laughs and gets Vincent to stop.]

In my notes, I don’t really have a specific question about it, but the discipline it takes to train for a marathon, I imagine, would be pretty similar to the discipline to complete a work that takes a year long. With writing, I’ve had to have that rote schedule, like I’m just going to do it every day like you have to do for running. And I wonder if you’ve had a similar experience. 

What I have found is when I’m disciplined in something like running or working out, that I’m much more inclined to be disciplined in creative pursuits. I think there’s something about getting your mind in the mode to do something that you might not necessarily want to do or feel ready to do. So, I think it does help to actually be doing something like running or working out or something else that takes discipline to also bring it into your creative life.

I feel like running also kind of forces you to explore the city in a different way than just walking around. When you’re running around, do you ever find something that you’re like, oh, that’s something I want to document?

Running really played a big part in the second Lakefront map that I did.

The one where it’s looking out to the lake?

Yeah. The first one, the focus was much more on the buildings and I wanted it to be very, very faithful to the skyline. And with the other one, I felt like the Lakefront itself was incredible. And especially for runners.


What do you get out of it when you’re sharing these obsessions?

I think it’s just enormously, I’m gonna say, reassuring, to get feedback from other people who felt the same way.

And putting stuff out there that you’re obsessed with, it just pulls other people out. Then you realize that there are other people out there who are also celebrating in their own way. You get linked to people that you should’ve known about, but were doing their own thing in their own different way. It’s this feeling that you’re joining this kind of brotherhood of people.

It’s almost community building, when you find something that’s underrated and then other people are like, oh yeah, we also think that’s underrated.

Yes. Yeah, it’s just a really good feeling.

If you’re going after the underrated stuff, it’s not going to inherently appeal to everyone, but it might have that super deep connection for that community that you’re finding.

Right, yeah, maybe just a few people will find a lot of use out of them.

By pursuing the stuff that I’m interested in, it’s really helped me focus my efforts and turn it into stuff that people ultimately respond to.


Visit Cape Horn Illustration. Many of the prints are roughly $30. Although I didn’t tell Thompson this, I bought “Chicago: The Marathon Map” and “Chicago to Chicagoans.” You can also follow Cape Horn on Instagram, where Vincent occasionally makes appearances.

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