Boxerian
Google
I've been trying to hit all of the big coffee roasters in Chicago and think this is a contender for the best in the city (at least top 4). It's located (fairly) deep into Chicago's southwest side but I think it's worth making an adventure towards.
They moved the shop a few blocks closer to the western orange line, which I am pretty sure was already where they roasted their beans. It means they have to work with very little, and on that end I think they've done a great job. The inside is very spacious and there's more than enough seating if you want to dine in. They also use their minimalist aesthetic to really play up the space theme by using an assortment of grays with a few branches that reds make the place pop. Their roasting machine could also be seen through one of their windows. I prefer this layout over a very stuffy interior, but just note that the company is selling itself more on its great food and drink rather than its sit-down atmosphere.
I'm not sure if they make their pastries in-house or not. But even if they're imported, kudos for having a good eye for sweets. I've gotten their brownies, almond croissant, and their pistachio-hazelnut danish and all of them have felt fresh and tasted great. No further notes.
Their coffee is the best part though. It's a lighter roast that's a little acidic. It is one of the most distinct coffees in the city and worth tasting. The acidic flavor may make it an acquired taste, especially if you prefer your coffee clear (you monster 😜), but the flavors really work when paired with something else. The coffee really is one of the best latte grounds in the city, and I'd argue the best coffee to have if you like to have something sweet paired with it.
Any negatives are mostly negated by the incredible price. You could buy a 16 oz. coffee for only 3 bucks. In comparison, any drip coffee from starbucks of any size will probably not be cheaper than $3.50 (the Starbucks website makes it a little vague so sorry if I'm incorrect). The grounds themselves are cheap too, with the 8oz. Bags being $8 in store and $9 on website.