4.6Three Dots and a Dash
River North · Chicago, IL · 0.4 mi
An alley of glowing skulls leads down to the loudest, most generous rum room in the Midwest.
Tiki Lounge
Illinois / Chicago
The Drifter
A former Prohibition-era hideaway beneath a River North tavern, where the menu is a deck of tarot cards and the cabaret runs between rounds.
Getting in
Through the tavern, down the stairs to the old ship's cabin.
Order this
Tarot card choice
Your passport
Hidden Door rooms like this one are catalogued across the trail — see every hidden door bar.
Keep the night going
Nearest doors
4.6
4.5The Berkshire Room
River North · Chicago, IL · 0.5 mi
Leather wingbacks, a smoking-jacket mood, and a Dealer's Choice card that lets you order by adjective.
Hotel Bar
4.6Andy's Jazz Club
River North · Chicago, IL · 0.6 mi
A former newspapermen's tavern that has run live jazz since the fifties — three sets a night, no attitude.
Jazz Room
4.5Milk Room
The Loop · Chicago, IL · 1.1 mi
Eight seats in a room that sold milk during Prohibition, now pouring bottles older than the building's current name.
Hotel Bar
The Gear Room
Drink like The Drifter at home
Death & Co: Modern Classic Cocktails
The East Village room on the trail, in book form. 500 recipes and the reasoning behind them.
$30–40Find it →
Regarding Cocktails — Sasha Petraske
From the man behind Milk & Honey, the room that became Attaboy. Spare, exact, opinionated.
$22–30Find it →
Nick & Nora Glasses (set of 4)
The stem that made the coupe look loud. Named for the most functional drunks in film.
$25–45Find it →
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