See What’s Happening at Todd’s
Once, Trader Todd’s was merely a port for lost sailors and fearless karaoke dreamers. Now, the adventure deepens—comedy crackles under tiki lights, DJs spin soundtracks for the bold, and burlesque blooms like forbidden orchids at midnight. Each week brings a new expedition, charted by laughter, rhythm, and a touch of the unexpected.
The Karaoke Expedition at Trader Todd's
You arrive unsure—half-expecting a bar, not an expedition. The air smells of pizza, pineapple, and possibility. A parrot squawks from above as laughter rolls across the tiki-lit room. Someone hands you a microphone; it feels heavier than it should—like destiny disguised in chrome. Then, as the music swells and your voice rises into the glow, you realize this isn’t karaoke. It’s discovery—your own legend set to a power ballad and the rhythm of adventure.
It was the sort of night that reminded you the future once had glitter-gel roots. Y2K Night with DJ Stitches unfurled inside Trader Todd’s like a neon time capsule cracked open with absolute confidence—where bass lines thumped with the sincerity of a dial-up modem trying its best, and the room glowed with the warm assurance of metallic eyeshadow and unearned optimism.
Two Girls One Windy City—part archivists, part adventurers—they guided the crowd through a world of butterfly clips, cargo pants, and the last era when a flip phone could shatter a heart. And as DJ Stitches stitched one anthem to the next, you felt something unusual: the strange, exhilarating suspicion that the year 2000 never really ended—it was simply waiting for you to return.
Chicago Party Clowns
12/18 25
A delightfully deranged holiday spectacular that unwraps the weird side of Christmas cheer!
Greetings from Santa’s most questionable helpers! The clown elves of Unwrapped & Unhinged have had one too many cotton candy canes and are ready to summon the holiday spirit by any means necessary.
Join The Chicago Party Clowns for a night of clown-forward burlesque, magic, and mayhem at Trader Todd’s Chicago. Watch as us nice & naughty elves clash with chaotic games and absurd seasonal shenanigans.
It’s camp and sparkle, unhinged. It's exactly the dose of unwrapped joy your weird little heart deserves.
Come laugh, cheer, and maybe compete for glory in this candy-coated circus of holiday absurdity.
Support your local clowns 🤡
VaVoom Lagoon Burlesque
Step out of the cold and into the swelter of Chicago’s hottest burlesque & variety entertainment! Hosted by Vera Sporadica.
A sexy mist beckons you...
Let winter melt away in the heat of fantasy as you're immersed in the presence of Chicago's hottest burlesque and variety entertainers! Bring your tipping dollars and your party hat - things are bound to get wild when the sun goes down over VAVOOM LAGOON!
Open Mic Night Wednesdays in the back Bar:
Hosted by Devin Glass 6:00 pm - 10 pm
Hosted by Devin Glass
TRADER TODD’S, CHICAGO.
Wednesday night, 6PM sharp—Devin Glass takes the mic like a lounge act reimagined by Hemingway, wrangling open mic comedy from the unhinged, the brilliant, and the heartbreakingly Midwestern. The scent of tiki glaze and pizza lingers as jokes fly looser than the rum pours, each set a high-wire act performed over a sea of pineapple-laden applause. It’s not polished, it’s not perfect—but neither was Sinatra, and he never had to follow a guy named Donny who only tells jokes about his ex-wife’s cat.
📅 Every Wednesday
🕡 Sign-ups at 5:45 PM | Show starts at 6:00 PM
Whether you're testing new jokes, debuting original songs, or just want to vibe with a supportive crowd, Trader Todd’s is the place to be. Grab a drink, take the stage, and let the good times roll.
