Why two completely different bars on the same stretch of Chicago real estate are where the city's singles are actually meeting each other.
Chicago does not do things halfway.
Not the architecture. Not the pizza. Not the winters, which arrive with a confidence that suggests the city is genuinely proud of them. Not the summers either, which last about eleven weeks and are treated accordingly — every rooftop, every patio, every outdoor seat in every bar in every neighbourhood filled with people who have been waiting since November and are going to make the absolute most of it.
And not the dating scene.
Chicago dating has a directness that distinguishes it from other cities. Not New York directness, which can tip into efficiency bordering on clinical. Not LA directness, which is mostly theoretical and dissolves somewhere on the 405. Chicago directness is warmer than both. More human. The city has a midwestern core that survives even the most urban of environments — a genuine interest in people, a willingness to actually talk, an absence of the performative detachment that makes dating in coastal cities feel like a particularly exhausting sport.
The apps, naturally, have done their best to sand all of that away.
But the West Loop is fighting back.
🗺️ Why the West Loop
A decade ago, the West Loop was still mostly meatpacking facilities and warehouses. Today it is one of the most energetic neighbourhoods in Chicago — Restaurant Row on Randolph Street, Fulton Market, the kind of density of good bars and interesting people per square mile that makes dating in person feel possible rather than aspirational.
Two venues in particular have become the Chicago home of MyCheekyDate events. They are completely different in almost every way. They are separated by less than half a mile. They are, between them, one of the better arguments for why the West Loop is where you want to be on a Saturday night.
🏗️ Venue One: The One With Chicago's Largest Patio
838 W Kinzie Street.
Recess started as the bar adjacent to City Hall — the event venue, not the government building, though the 40-foot wooden bar does anchor the room with the kind of authority that suggests it has been there at least as long as the Daleys. The roll-top glass-paneled garage doors open directly onto the patio. The dining room is awash in natural light. The leather chairs, bar stools and tufted couches are exactly the kind of casual that takes effort to achieve.
Then there is the patio.
Chicago's largest, by every account that has bothered to measure it. Surrounded by shipping containers — two of which open up and convert into bars — with a raised central platform, second-floor container levels available for quasi-private groups, fire pits in cooler months, and the kind of open summer energy that makes you understand why Chicagoans treat June through August as a separate and sacred season.
The name is deliberate. Recess is what you do when the pressure lifts. Giant Jenga. Connect 4. Board games. Large-format drinks wheeled to the table in tabletop-sized water coolers. The whole concept encoded in one word: adult... like a kid.
For a speed dating event, this energy is exactly right. Not precious. Not intimidating. Not the kind of venue that makes you feel like you need to perform sophistication before you have established whether you actually like the person across from you.
Just: show up, be yourself, see what happens.
And if it does not happen — there is giant Jenga.
🎨 Venue Two: The One That Stops People at the Door
401 N Morgan Street.
Tabu is everything Recess is not, in the best possible way.
Where Recess is expansive and playful, Tabu is intimate and electric. Where Recess feels like a great Saturday afternoon, Tabu feels like a Saturday night that could genuinely go somewhere.
The ceiling is adorned with nearly 10,000 individually cut ropes. There are enigmatic pop art murals on the walls. There is a sunken cocktail lounge that, in the words of everyone who has described it, begs you to order just one more round.
The drinks programme claims the largest collection of mezcals and tequilas in Chicago. The kitchen is run by Executive Chef Saúl Román — a Cuernavaca, Mexico native with years of experience in Mexico City — delivering Pan-Latin cuisine that draws from Mexico, Spain, Colombia, and beyond.
Choose Chicago calls it "unique and eclectic." That is the restrained version. The accurate version is: Tabu is one of the most visually arresting interiors in the West Loop, designed by people who understood that the room itself should do something to you before you have even looked at the menu.
And something it does.
You walk in, look up at the ropes, look around at the murals, slide into the sunken lounge, and feel something shift. The city outside is still there, but it is quieter in here. More focused. More charged.
Which is, again, exactly what a speed dating evening wants from its setting.
😏 Two Venues, One Idea
Both Recess and Tabu are part of the same hospitality group. Which means there is a deliberate logic to how they have been designed — not competing with each other but offering something different to different people at different moments.
Younger crowd, summer energy, patio vibes? Recess has you.
Something more charged, more atmospheric, more designed to make the evening feel like it could be memorable? Tabu is ready.
MyCheekyDate runs different age groups at each venue across the week, which means the events are matched not just to who is coming but to where they will feel most at ease.
This matters more than it sounds.
Because the biggest enemy of chemistry is not incompatibility. It is self-consciousness. People performing a version of themselves because the room made them feel they needed to. The right venue removes that performance. It makes people relax. And relaxed people — as every MyCheekyDate host will confirm, and as the Smart-Card data consistently shows — produce better matches.
Recess relaxes people by being playful. Tabu relaxes people by being extraordinary. Different methods. Same result.
📍 The Events
Ages 25–39 | Wednesdays & Tuesdays | Recess, 838 W Kinzie St, West Loop | 6PM Early Bird from $32.95 → Book here
Ages 36–48 | Sundays | Recess, 838 W Kinzie St, West Loop | 6PM Early Bird from $32.95 → Book here
Ages 25–39 | Saturday Nights | Tabu, 401 N Morgan St, West Loop | 7:30PM Early Bird from $32.95 → Book here
Ages 27–42 | Saturday Nights | Tabu, 401 N Morgan St, West Loop | 7:30PM Early Bird from $32.95 → Book here
Ages 32–44 | Sundays | Tabu, 401 N Morgan St, West Loop | 5PM Early Bird from $32.95 → Book here
Note: Saturday night events at Tabu have been selling out. Men's spots in particular go quickly — check the current schedule and book accordingly.
Full schedule at mycheekydate.com/speed-dating-chicago
🥂 The Cheeky Truth About Chicago Dating
Chicago is genuinely one of the best cities in the country for meeting people.
The warmth is real. The directness is real. The willingness to actually have a conversation — rather than a carefully curated text exchange that builds toward a meeting that may or may not happen — is real and refreshing.
What the apps do to Chicago dating is take all of that warmth and directness and filter it through a medium that rewards neither. Swipe-based dating in a city that was built for face-to-face interaction is a bit like trying to appreciate architecture through a keyhole. You can see something. But you are missing most of what makes it worth looking at.
The West Loop in summer, on the other hand.
A rooftop-scale patio. A sunken lounge with 10,000 ropes overhead. A structured evening that puts you across from real people having real conversations. A city that, given half a chance, shows you exactly why it was worth showing up for.
Chicago doesn't do things halfway.
Neither does a good first conversation.
MyCheekyDate has hosted over 1,700 speed dating events in Chicago. Host-led. Smart-Card matched. No swiping, no performative detachment, no "let's grab drinks sometime" that never happens. Just the West Loop, two exceptional venues, and four minutes to find out. Find your Chicago event →