Cafe Robey

Perched at the triangular intersection of Milwaukee, Damen, and North, Cafe Robey offers prime people-watching from its sidewalk seating—a front-row ticket to Wicker Park's endless parade of characters. The cocktail program punches above its weight, with seasonal concoctions that balance creativity and drinkability (try anything with their house-infused spirits). While tourists dominate the scene, the staff maintains a refreshingly unpretentious vibe despite the stylish surroundings.

The food menu elevates the drinking experience from "acceptable" to "actually worth planning around," with shareable plates that won't leave you hunting for a late-night taco afterward. Yes, you'll need a reservation during peak hours, and yes, parking is the expected urban nightmare, but that's the tax you pay for drinking at one of the neighborhood's most distinctive corners. Come with the family for an early dinner or claim a sidewalk table for evening cocktails—just don't expect a craft beer revelation with their limited selection.