Where I Get Coffee in Chicago

Read my suggestions, but make your own neighborhood map

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Everyone should have their own personal coffee map.

Lists make me uncomfortable. A top-10 article about “the city’s best X, Y, Z…” can make or break a business, but even the best-researched round-ups are rarely clear about how their rankings are determined, or up-front about their inherent limits and subjectivity. As others have pointed out, prestige is often bestowed unfairly, rewarding familiarity and in-group favoritism.

Regardless, people regularly ask me where the best places are to get coffee. As someone who works in the industry, I feel uncomfortable making recommendations—as hard as I try, I know they will still be influenced by my own bias, and that any claims of goodness risk sounding like definitive truth. Instead, I like to think smaller and more personal. As a steward of my neighborhood, I’m happy to share where I like to walk to, ride to, or take a stroll with my dog to.

Truthfully, what matters most to me is that my coffee is brewed by neighbors. I rarely care about much more than that.

Making a neighborhood map is as simple as listing the places you like to visit. If a friend were staying over the night, where would you casually stroll in the next morning? Free of best-of list and top-10 rankings, where do you find yourself coming back to over and over again? That’s your neighborhood map.

With that in mind: I live in Humboldt Park in Chicago, and this is where I like to go for coffee.

The Place I Go the Most: Four Letter Word. Technically, Four Letter Word (often styled as 4 Letter Word, or simply 4LW) is a stone’s throw away in neighboring Logan Square, but I can ride straight up a bike path and end up at what I’d argue is my favorite coffee shop in the city. I worked here when it first opened, and I frequent it as a customer now. If you’ve read any of my writing, you know how critical I can be of former employers—but my time at Four Letter Word stands out as absolutely wonderful.

If you’re looking for a group of skilled baristas, they’re here. Everyone who’s worked at Four Letter Word has cut their teeth at some other shop, in Chicago or elsewhere, and together they foster a welcoming and unpretentious vibe. You can get your drip coffee and leave, or you can inquire about the rotating single origin menu. It takes all kinds—and it doesn’t hurt that Four Letter Word is also across the street from a wine store.

A Place that Cannot Be Replicated: Damn Fine Coffee Bar. Who opens a Twin Peaks-themed coffee shop? Who makes the theme so subtle that it takes certain people dozens of visits to recognize it? Damn fine coffee? C’mon, Ashley.

Damn Fine is not a place you’re likely to find by accident, and it feels like the regulars have been coming to this coffee shop for decades. It’s the type of place that fosters a close-knit feeling: Damn Fine regularly shouts out its staff by name on Instagram, and I get the sense most followers know who they are. I have to imagine that if someone posted a sign in the window saying, “Hey, Debbie is sick, we’re not open today,” everyone would just nod their heads and be cool with it. This recent photo especially tickled me (one of the comments comes from the poster’s mom).

Grab a Coffee, Grab Some Pie: New Math Coffee. A new roaster focused on Asian coffees, New Math does occasional pop-ups in the city, including at Spinning J, a lunch-and-pie-counter shop that’s next to a charming wine bar with a killer burger. If there’s no current pop-up, you can still order coffee online or as part of Weird Thyme’s CSA.

People Doing Awesome Work: Atmos Coffee. I used to chat off and on with Antoine, one of the founders of Atmos Coffee, before he and his co-owner (and wife) Arianna took over an old, formerly shuttered shop. We’d started talking as fellow members of the Chicago coffee world, and I was thrilled to learn they’d be opening so close to where I live.

Although COVID restrictions have made Atmos’ grand opening a little different than what was initially envisioned, the couple does have a plan to roll out a job readiness program for Black and Latinx youth. They’ve also been open about the gatekeeping inherent to the city’s coffee circles, and have made it a core value that they want to be as forthcoming with information and education as possible. Basically, these people rock, and I’m sad I haven’t met them IRL yet.

If I’m Feeling Jaunty: Everybody’s Busy. I interviewed owner Melissa for the second time on the latest episode of the podcast to learn more about her vision for Everybody’s Busy. What’s true is that every time I visit feels like an occasion. Not only is Melissa quality-driven, but she’s serving coffee in a carefully designed space. Melissa leaves no detail to chance.

Everybody’s Busy is a bit of a trek for me—Pilsen is about a 20-30 minute drive away—but Melissa is part of my community, and nobody has a space like hers. She’s a visionary.

Before you go…

I like to pretend that I’ll be on Jeopardy! one day, even though I know I won’t—I’m simply not good at trivia. Instead, I can turn to Claire McNear’s book, Answers in the Form of Questions. It talks about Jeopardy! like it’s a sport, breaking down the strategy and giving us an inside peek into the culture of the show and its fans. It’s perfect.

Roxane Gay is doing a Masterclass on writing for social change, which is the first time I’ve ever been tempted to sign up for these classes.

“Stop Telling Women They Have Imposter Syndrome” is an article by Ruchika Tulshyan and Jodi-Ann Burey about how women often interpret their own self-doubt as a symptom of “imposter syndrome”: the belief, often experienced by marginalized people, that they’re not working hard enough, or don’t deserve their work or position. They argue that this tendency masks the real harm being done to women, who are often talked down to and discriminated against. Their article encourages folks to move away from individual notions of feeling like a fraud to examining why scores of people—mostly women—continue to feel like they don’t belong at work, and which systems reinforce this notion.

Also, I made a caramel cake.

Last week was a really great one for Boss Barista: My piece on the reasons and intentions behind opening up coffee shops has been viewed more than any of my other newsletters, and brought in a bunch of new subscribers. If you’re new to Boss Barista, I’m so glad you made it here—thank you for signing up!

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