The night begins with the rumble of a train rushing above the Ashland Green Line station. A short walk away, surrounded by warehouses and small manufacturing facilities, an emerging distillery operation is the only sign of activity on this empty street. It’s where cool hangout spots aren’t supposed to exist. Or maybe that’s why it’s cool. We’re drawn by that voice inside our head that sometimes whispers, “Hey, let’s check out where this dark alley leads.”
While it’s quiet outside, there’s a flurry of activity upon entering the taproom. A small crowd of friends lines up at the bar, listening intently to the bartender as he shares the story behind the spirits in their flight, each inspired by a different piece of Chicago history.
Named after where the three branches of the Chicago River meet, Wolfpoint and each of their spirits are one big ode to Chicago.
The idea for the distillery itself was born out of a conversation in a Chicago bar. Pavlos Dafnis and Victoria Polvino, a husband and wife team, own and operate Wolfpoint alongside their lead distiller, Steve Dethrow.
I’m willing to bet we’ve all had lively conversations with friends about making bathtub whiskey and starting a business together, but this is what it looks like when you actually make it happen.
Polvino takes on the gargantuan task of navigating the regulatory rules required to keep manufacturing operations compliant.
Dafnis and Dethrow conduct distilling chemistry experiments in their library full of botanicals. And when they have a minute, one of them loads up a car and drops off orders to liquor stores, bars, and restaurants across the area.
The taproom is open Thursday – Saturday with public tours in the early evenings. This isn’t some highly-automated operation. Each bottle is painstakingly hand-labeled and filled.
Polvino and Dafnis hang out in the taproom and tend to things like the gracious hosts they are. The atmosphere is relaxed. It feels like having a drink at home. A movie projects on their brick wall and plays in the background. Another group brought in pizza and is setting up for what looks like an intense board game session.
It’s only the start to a great night. Hang out here for a bit, and then move on to dinner at a nearby basement wine bar.
The evening continues a few blocks away on a quiet corner of an otherwise bustling West Loop neighborhood. You’re finishing the night at Press Room, a basement wine bar and restaurant where the mood is some cross-section between contemporary gothic, bohemian, and with a splash of art deco.
You’ll walk into an inconspicuous building and follow the glow of a well-worn candelabra illuminating the basement entrance at the bottom of these stairs.
I like to think of this place as the “Everything, Everywhere, All At Once” of restaurants. It can be anything to all people; a place where you’d be just as comfortable coming dressed up for an anniversary dinner or dressed down in a Bulls jersey for casual drinks.
For operating partner Paul Mena and Chef De Cuisine Christian Sia, cultivating this warm and welcoming environment is a natural byproduct of being outsiders themselves. Both Mena, originally from Ecuador, and Sia, originally from Singapore, started in Chicago’s culinary scene as outsiders looking in, but now that they’re running show at Press Room, they’ve managed to create something really special that says, “Hey, you belong here.”
While the dining room hums effortlessly, it’s a sprint in the small kitchen. Camouflaged behind a gossamer black veil next to the bar, it’s a three-person show in the back with Sia at the helm and Michael McCants, a veteran of the Chicago culinary scene, as sous chef.
The sweet potato risotto simmers on the stove, tended to with clock-like precision. Over at the plating station, the chefs put the finishing touches on a velvety veal tartare adorned with rice paper crackers and a generous dollop of caviar. Meanwhile, a new order comes in for their Nashville hot-dressed quail.
This is what modern American cuisine looks like – an eclectic mix of flavors and techniques drawn from the team’s diverse backgrounds—no rules, no boundaries – just good food.
We visited during the week, and the first guests came in at 4 pm to take advantage of their $1 oyster happy hour and $20 meat and cheese board.
Within the hour, the dining room started to fill up. Make reservations if you can, but they always seem to have a few spots at the bar for walk-ins. 
We end the guide with a few pics of our half-eaten meal. Their menu always changes, so expect something different each time you visit. But before we go, we asked Sia and Mena for their personal Chicago restaurant picks. Here they are:
1. Same Same
2. Virtue
3. Kasama
4. Jeong
5. El Asadero Colombiano
6. Dona Torta Chilanga
7. Carnitas Urupan
 