Chicago's whiskey pedigree is generational: Delilah's on Lincoln has poured one of America's great whiskey collections over punk records for decades, and Longman & Eagle in Logan Square backs its Michelin cooking with 300-plus whiskeys. Gold Coast smoke, Lincoln Avenue pour.
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A Chicago institution, hundreds upon hundreds of whiskeys poured over punk and honky-tonk records. One of the great whiskey bars of America, zero pretension.
Pip’s Tip Bring cash. Hundreds of whiskeys poured over punk and honky-tonk records in Lincoln Park.
Michelin-starred cooking with 300+ whiskeys behind the bar, Logan Square's whiskey tavern, with an inn upstairs if the night runs long.
Pip’s Tip Michelin-starred kitchen with 300-plus whiskeys behind the bar, and rooms upstairs if the night runs long.
A candlelit River North salon known for its interactive Dealer's Choice cocktail and expert-led bourbon-and-scotch tastings.
Pip’s Tip Opens 7pm Sunday and Monday, earlier the rest of the week. Ask for the Dealer's Choice.
James Beard Award-winning pre-Prohibition cocktails behind an unmarked, ever-changing mural facade, Wicker Park's most iconic hidden door.
Opulent American classics upstairs; downstairs through a discreet doorway, The Library nods hard to Chicago's speakeasy past.
An award-winning Logan Square cocktail room built on a deep library of vintage spirits, amaro, and fernet.
One of the largest American whiskey collections in the world, poured inside an 18,000-square-foot Prohibition-era supper club with nightly live music.
Chicago's oldest tavern (est. 1921) hides its true speakeasy in back, the last surviving Prohibition-era room in the city.
A fire-roasted Gold Coast steakhouse whose upstairs Nightcap lounge turns into the neighborhood's best late-week whiskey hang.
A sprawling Loop beer-and-whiskey hall with a chef-driven menu and enough taps and pours to settle any argument.
Chicago's most iconic piano bar, live music seven nights a week, a cigar menu, and drinks that keep pace until sunrise.
A supper-club-inspired Loop steakhouse with a 500-square-foot dry-aging room and a bar program to match the beef.
A Japanese dining bar from beverage visionary Julia Momosé, sake, precision cocktails, and a blue door that's easy to miss on purpose.
Chicago's oldest restaurant, family-run since 1898, a Loop institution with a classic bar and 125-plus years of stories.
A no-cover Logan Square gallery-bar hybrid, craft cocktails, live jazz jams, and a rotating art install on the walls.
The downstairs tavern beneath three-Michelin-starred Smyth, relaxed comfort food and a cocktail list with the same obsessive care upstairs.
A punch-bowl bar beneath historic Thalia Hall, whiskey, rum, and pisco punches poured to a nightly soundtrack of disco and funk.
A dim, velvet-draped Parisian-steakhouse saloon with an old-world bar program built for a bourbon nightcap after the porterhouse.
Decades of whiskey wisdom on Lincoln Avenue, one of the deepest collections in the country, poured without ceremony. The kind of room that remembers you.
One lounge, one whiskey bar, one golden evening. Members hear first.
Every whiskey bar here pairs with a PIPS cigar lounge across town, see the Lounge Guide for the other half of the evening.
