Chicago Day One. Chicago River, the Magnificent Mile, and 550 Bottles of Whiskey
If you missed the first post in this series, start here — it covers how we got to Chicago, which was its own adventure.
Jon and I got married on November 1st, 2025. Our theme was a 1920s speakeasy. So when I was planning our Chicago trip and ChatGPT mentioned that the city had a venue sitting on the largest collection of American whiskey in the world — tucked underground, Prohibition-era inspired, with live entertainment — obviously we had to go!
But first. The river.
We started day one with the Chicago Architecture Center River Cruise aboard First Lady — a 90-minute boat tour that every Chicago first-timer should do. Chicago didn’t just accidentally become one of the most architecturally significant cities in the world. The Great Fire of 1871 wiped out most of downtown and handed a generation of visionary architects a blank canvas. What they built in its place — steel frames, plate glass, soaring verticality — gave birth to the modern skyscraper. The river cruise takes you past more than 50 buildings that tell that story, from the ornate Gothic revival facade of the Tribune Tower (with stones embedded in its exterior from the Parthenon, Notre Dame, and the Berlin Wall) to the twin corncob towers of Marina City to the undulating wave-like balconies of the Aqua building. Art Deco, postmodern, Beaux-Arts, glass-and-steel brutalism — it’s all there, right on the water, while a volunteer guide who genuinely loves this city connects the dots between them.
We upgraded to priority boarding. Completely unnecessary — it wasn’t busy. The best spot is the open-air upper deck, but it was late March and cold, so we settled inside by the back windows. Still great views, though the narration is harder to hear inside.
By the time the tour ended, the people who’d started on the upper deck were filing inside, having reconsidered. If you go — and you should — book in advance. It sells out, and once you’re on the water looking up at what this city built, you’ll understand why.
The Magnificent Mile
After the cruise we walked the Magnificent Mile. We’re not big shoppers, so this was less about retail and more about being in it. Michigan Avenue was wall to wall people — the kind of crowd Jon said he genuinely couldn’t remember seeing on a single city street. He stopped to take a photo just to document it. Even if you have zero interest in shopping, the energy is worth the walk.
We’d had grand plans for a Chicago hot dog somewhere along the way. But we don’t eat like we used to, and I looked at that thing — neon green relish, sport peppers, raw onion, pickle spear — and did a quick mental calculation against the big dinner we had planned. We decided we’d leave something for next time.
Somewhere along the Magnificent Mile we stumbled onto the Chicago Sports Museum, tucked into the seventh floor of Water Tower Place inside Harry Caray’s restaurant. Jon explained who Harry Caray was — the legendary Cubs announcer who led the whole stadium in “Take Me Out to the Ballgame” during the seventh inning stretch. Then we googled the museum. The Bartman ball. Sosa’s corked bat. Kris Bryant’s cleats from the final play of the 2016 World Series. We stopped and checked it out.
Untitled Supper Club
I’d been looking forward to this one since I found it. We were celebrating our five-year anniversary as a couple — and with a speakeasy wedding still fresh in our minds, an underground venue sitting on the largest American whiskey collection in the world felt like the universe knew what it was doing.
From the outside, you’d walk right past it. A black kiosk on the sidewalk. Gold script. No fanfare. What’s inside is one of the most remarkable venues I’ve been to anywhere.
You walk through the entrance and head downstairs into an 18,000 square foot underground space spanning multiple rooms, each with its own personality and its own wall of whiskey. The Library holds over 550 bottles — rare bourbons, collectible ryes, limited releases — lit up against the walls like something out of a dream. The whole place feels like it was built by people who take both whiskey and a seriously good time very seriously. It’s also a seven-time Michelin Bib Gourmand restaurant, which means the food program is as thoughtful as everything else.
We were seated in the Cabaret Room, front row by the stage. The room is draped in dramatic wallpaper — dancer silhouettes in deep crimson and purple — with low red lamps on every table. Exactly what I’d pictured and then some.
I started with a whiskey flight. Three glasses on a wooden board, each one worth paying attention to. Then moved to a Savage and Cooke Burning Chair — a premium bourbon, with a richness that sat perfectly in that room. For dinner I had the scallops, a special that evening. Jon had steak. We shared crunchy potatoes. And because we were celebrating our anniversary, the kitchen sent out a chocolate cake with cream. We didn’t ask for it. It just appeared. That’s the kind of place Untitled is.
The band that night was the Hemispheres — a full ensemble with horns, keys, guitar, and a lead female vocalist who could really sing. The kind of band where you stop mid-conversation because what they’re playing is too good to talk over. During their break, a solo burlesque performer took the stage. The crowd — many of whom had shown up in full bling — was completely delighted. So were we.
Here’s what we didn’t know until after: every Thursday, Untitled hosts Unbridled, a full burlesque show. We were there on a different night and only got a taste. If we’d known, we would have planned around it. Check the calendar before you go. If it’s a Thursday, don’t miss Unbridled.
We walked out well fed, well poured, and very glad we’d found the place. A good night by any measure.
Chicago was off to a very good start.
Untitled Supper Club is at 111 W Kinzie St in River North. Reservations recommended. Ask for the Cabaret Room if you want to watch the band or see the show. Check the entertainment schedule.
The Chicago Architecture Center River Cruise aboard First Lady departs from the Riverwalk at the southeast corner of Michigan Avenue and Wacker Drive. Book in advance — it sells out.
