Pilsen-Bridgeport Coffee Tour
Exploring two cool Chicago neighborhoods via coffee shops and "adequate" bike infrastructure!
Another coffee tour! This time, of the Pilsen and Bridgeport neighborhoods Southwest of the Loop. I picked a Saturday and a friend, and made the 50min bike ride in the brisk November Autumnal morning, and headed down to two neighborhoods I’ve barely yet visited.
And unlike my last coffee tour, I’ve built some things on my website to streamline this process a bit :3 Enjoy the commentary but feel free to scroll down to the quick-n-dirty summary + scoring for each one!
They’re in the style of my full cafe reviews, just probably without a dedicated page.
The Map
The goal was for somewhere both bikeable AND accessible by transit in the future
The Outing
Anticonquista
The only shop on the trip today that I’d already visited, Anticonquista Cafe was high on my list to re-visit, especially with my friend.
As a coffee snob, I wasn’t overly impressed with the quality of coffee this time or last, but it was good, and more importantly, I am in love with their mission and the politics of their shop.
They really don’t make agitprop like they used to!
As a huge proponent of combatting white Western chauvinism, places like this are a precious goldmine of accessible education and perspective.
Never seen a handmade mug like this at a cafe
I enjoyed my coffee, though it was yet another shop that gave me this^ when I asked for a small, 8oz americano so. I don’t know what’s up with that.
Solid though! Not mindblowing, but genuinely very comfy, tasty coffee.
This place is utterly unique. It doesn’t fit in to my tidy “work from home” coffee shop paradigm, but it feels cool being there, and engaging with an honest business with a genuine anticolonial foundation. Very rad.
Anticonquista
A family-run shop defined by its anticolonialism, this shop serves coffee exclusively from their family farms, and features wall-to-wall anticolonial propaganda & decor plus community resources.
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coffee 6 / 10 -
cafe 4 / 5 -
price 2.5 / 5 -
productivity 3.5 / 5 -
vibes 5 / 5 -
Total
21 / 30
Cup of Joe - Pilsen
This place really surprised me! It’s a very small space, so it clearly serves as a tidy “grab food + coffee and go!” purpose in the area, but honestly the food and coffee were surprisingly good!
Yes, a 5/10 is a “surprisingly good!” coffee by my ratings lol. I’m pretty decent at avoiding BAD coffee, so my rating system scales down.
Really cute branding and pretty dang solid pricing overall!
This is the WHOLE cafe, minus the bar seating at the window
I enjoyed my Americano, and the vibes were very nice. Not exactly a place to hunker down and get some work (or website coding) done, so I probably won’t be back unless I’m meeting an acquaintance nearby.
A Cup of Joe - Pilsen
A tiny community shop with good vibes and pretty good food. Maybe not an all-day work 'n stay but cute enough to stop into for a quick cuppa, especially for the price!
- coffee 5 / 10
- cafe 2 / 5
- price 4 / 5
- productivity 1 / 5
- vibes 4 / 5
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Total
16 / 30
CTRL Z
This is the entire cafe, save for 4 window bar-seating spots to the right
Ctrl Z might be the biggest disappointment of the trip, but I don’t think it’s hopeless. I took the barista’s recommendation for a type of drink (the name of which I’ve forgotten), and it amounted to a very roasty, mid-tier pour-over.
Not bad but I’d heard a lot of good things about this place so…
Incredibly competitive prices, so big fan of that. They offer a wide enough array of flavors and options that I feel like I could easily bring most friends here and find them something they’d like.
All medium roasts…hmmm
I’m fast learning that there are a good many high-tier, Southeast Asian specialty coffee shops. Love the ubiquitous ube syrups they all offer (ube is so so good, y’all), but also they tend to source/roast very interesting beans!
The could brew things are pretty rare, but invariably in my experience indicate a serious coffee shop
They’re clearly serious about their preparation. And it’s still pretty tough finding a good pour-over in this town, so I plan on coming back. The drink I got on this trip just wasn’t super impressive!
Points for creativity lol but I couldn’t sit here long
Interesting space with interesting coffee options…deserves a 2nd chance. Not super accessible by transit, but that’s why we’ve got bikes!
Ctrl Z
A strange, very small cafe with unique coffee offerings. Not a place to go and get work done, but unique coffee and funky seating good for a casual conversation.
- coffee 7 / 10
- cafe 2 / 5
- price 2 / 5
- productivity 1.5 / 5
- vibes 2.5 / 5
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Total
15 / 30
Bad Owl Coffee Roasters
Absolutely NOT a hoot
Ho boy. Hooo man.
First off we gotta talk about the roasting machinery situation. I’ll refer to my rant in the Caffe Umbria review, but TL;DR any coffee roaster with their machinery out in the open like this is not serious.
On a more specific note here, what the hell is the deal with the two bar seats just facing the roaster?? If that thing is running anyone there is going to get blasted. Plus it’s so loud!
Okay I’m ranting again. Moving on.
I heard good things about Bad Owl (from reddit) but just from my maps sleuthing I could tell it was probably nothing too special.
Cute.
Full coffee flight review below, but suffice to say I was not impressed.
I talked to the barista, told them it was my first time here and wanted to order something that’d really show me the value of Bad Owl. They thought for a minute, and then recommended this coffee flight.
It had:
- Espresso
- Cortado
- A banana nut latte cold brew (apparently they’re really popular)
- A non-coffee drink they likened to “butter beer”
The espresso was OK. At tasting I told my friend “it’s the pinnacle of average medium-roast espresso”, as in, (generously) it’s just about as good as you can get from unremarkable espresso.
The cortado was awful. Just awful. The milk was flat, and the espresso tasted empty.
The banana thing was like, fine. But I don’t care about sweet cold brews so I’ll be neutral on that.
The butter beer thing was tasty because it was a sugary non-coffee sweet drink. Again, not coffee, so /shrug.
There’s just something suspicious about that gecko…
I wish I could say I love their coffee bags because at first glance they’re very pretty and cool!
But I can’t shake the feeling that they’re made with AI art…and I just don’t trust that.
Why put it in the middle of the floor, but then “hide” it with cheap plastic plants?
The vibes are off. The coffee is off. I don’t really know who this is for, but at the very least not me.
Bad Owl Coffee roasters
A California roastery transplanted into a Chicago neighborhood. Feels anodyne and unserious, but wants to be taken seriously. Possibly good coffee, but yet to be impressed. Weird amount of fake plants juxtaposed to genuinely decent real pothos so idk what's going on
- coffee 3 / 10
- cafe 2 / 5
- price 2 / 5
- productivity 2 / 5
- vibes 1 / 5
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Total
10 / 30
Jackalope Coffee & Tea House
The final stop on our little coffee tour, this was absolutely the overall highlight for me.\
- Pretty dang good coffee
- Interesting media and trinkets everywhere you look
- Tons of space, and rooms of different volumes/activity
- Community board games
It has it all!
I think I spent no less than 10 minutes just craning my neck looking at things
There’s a lot I look for in a cool cafe. Coffee, sure, but also places that I’d enjoy taking my friends to! And Jackalope really feels right.
I don’t have a whole lot more to say about the cafe that the pictures don’t say for me. It’s just neat! And I’m serious, the coffee (and pistachio donut we got) was really really good!
Not 9/10 good, sure but I’m picky…and picky as I am, that regular-ass americano was no less than a 7/10!
Mars attacks!! Iconic af!
Jackalope Coffee & Tea House
An eclectic cafe with tons of space, style, and charm but doesn't compromise on the coffee quality. It feels utterly unique and authentic, full of neat tchotchkes
- coffee 7 / 10
- cafe 5 / 5
- price 3 / 5
- productivity 3.5 / 5
- vibes 5 / 5
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Total
23.5 / 30
Closing Thoughts
This was even more fun than the previous coffee outing, partly because I biked, but also I think I just found cafes more representative of their respective neighborhoods (with the one exception), and that made a big difference.
Just Northside Things
Chicago is a historically segregated city, and only the delusional would suggest it isn’t still struggling with that history.
As a somewhat-recent transplant to Chicago (2022) and as a communist who lives on the wealthier, whiter Northside of Chicago, how do I contend with that? What do I do to both resist the chauvinist, alienating effects of that material reality?
I don’t have a great answer to that. But I feel that the lowest hanging fruit would be to visit and engage with the other neighborhoods in the city. And I strongly believe that community coffee shops are an excellent stepping stone for an outsider to mingle!
So many great books here. I nabbed that copy of The Red Deal!
For someone on the Northside, what would bring you all the way to Pilsen or Bridgeport? For the average person, probably either a special event or friends.
And I suppose that’s true for me too. I first visited Pilsen a few months ago when South Loop friends took me on a bike ride from the loop over to Anticonquista. Ever since then I’d been trying to come up with a good excuse to travel over there.
A bit of the local fabric
Cruising through a few streets between coffee shops is hardly a thorough exploration of a neighborhood but it really planted a seed in me. I have two good coffee shops worth coming back to, but I also have countless sights of things I biked past that my friend and I called out–things worth another visit.
We briefly stopped into Hoofprint here to check out the art :3
Biking down 18th St in Pilsen was a joy, passing all the vibrant Mexican-American art adorning the shops and restaurants along the street.
Crossing the bridge over to Bridgeport, almost missing Ctrl Z coffee shop for how simply it slotted into an old factory building…things like that really stuck with me.
I’m proud to call Chicago my home, and I’ve only ever been rewarded for exploring outside my hyperlocal sphere and seeing what else the city has to offer, and how all my cool neighbors live and support one another with hot brews and cool spaces UwU
Comfort in simplicity…also still thinking about the really cool black & blue e-bike my friend and I saw while at Cup of Joe. @ that cyclist: hiiii thanks for chatting with us your bike is sick I hope I wasn’t too weird asking questions about your e-bike I just thought it was neat
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Hi, I'm Regal!
I'm a communist cobra obsessed with coffee, weightlifting, and Chicago! This is my personal site where I blog about coffee shops and other things. 
Thanks for stopping by! Hit me up on the socials if you have any comments or want to say hi, or if you've
got any cool coffee shop suggestions here in Chicago 
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