California Clipper

Hospitality group Orbit Group (Segnatore) revived The California Clipper, founded in 1937, after a brief closure during the pandemic. These days, the signature red leather booths, vintage decor and live music make this post-prohibition-inspired spot one of the city’s best bars.

The vibe: A dim red glow invites you into this iconic Humboldt Park cocktail lounge. Most nights, you can catch live music performances, from DJ sets to funk, blues and jazz jams. 

The food: Food isn’t served here, so plan on eating before or after your visit. If you’re in the mood for Italian, Orbit Group's other spot, Segnatore, is directly across the street.

The drinks: Despite the bar’s deliberate “classic Chicago tavern vibe,” the cocktail menu offers much more than a Chicago Handshake—though they do offer that for $8. The seasonally rotating menu features interesting takes on familiar favorites like the Mezcal Soda Highball, Yuzu Spritz (yuzu sake, sparkling wine, soda and rosemary) and the Basil Gimlet (Condessa gin, basil, lime and mole bitters).

Time Out tip: If you’re craving a change of pace, venture to the Clipper’s back room (which previously housed coffee shop C.C. Ferns) for DJ sets and late-night dancing meant to channel the spirit of Danny’s, the iconic Bucktown spot that shuttered in 2020.