Editorial
Chicago has a better bar city than it gets credit for. The conversation about American cocktails tends to start and end in New York, but the editors who have spent serious time in both will tell you that Chicago's best bars operate at the same level and sometimes higher. The Violet Hour set the standard for serious craft cocktails in the US before most New York bars caught up with the concept. The Aviary redefined what a cocktail experience could look like. Logan Square has produced more interesting neighbourhood bars per block than almost any equivalent stretch in Brooklyn. This itinerary covers all of it.
The route starts in Wicker Park and moves through the West Loop, Logan Square, and River North, finishing in the Gold Coast. Chicago's L Train covers the main corridor, but Uber between River North and Logan Square is recommended after 10pm. The stops are 15 to 25 minutes apart by transit.
The Violet Hour opened in 2007 and changed the standard for what a serious American cocktail bar could be. The room is partitioned by heavy velvet curtains, the menu is handwritten, and the silence policy at the bar is not a gimmick: it creates a room in which the quality of the drinks is the only thing that competes for attention. Chicago's cocktail bar scene has The Violet Hour as its founding document. Arrive before 6:30pm for a walk-in table.
A gin-focused bar in Logan Square that operates without the reverence of The Violet Hour and is better for it. Scofflaw is loud, welcoming, and serves some of the best gin-based cocktails in the country from a menu that changes with genuine regularity. The bar top seats are the right seats. The beer selection runs to 8 well-chosen taps from local breweries. At this hour Logan Square is just beginning to fill and the pace is still comfortable.
Paul McGee's tiki bar in Logan Square is the best of its kind in the Midwest and makes a serious argument for being one of the best in the country. Lost Lake takes the tiki tradition seriously without being reverent about it, uses fresh-pressed juices and house-made syrups throughout, and has a rum list that runs to 250 bottles. The food is better than a tiki bar has any right to produce. One of Chicago's most underrated hidden gems for serious drinkers.
Grant Achatz and Nick Kokonas opened The Aviary in 2011 as a direct companion to Alinea, and it operates on the same principles: every element of the cocktail experience is designed at the technical level of a three-Michelin-star kitchen. A reservation is required for the main room. The front bar takes walk-ins on a first-come basis. At 10pm on a weekday the wait for front bar seats is typically under 30 minutes. This is the stop that justifies the full evening.
Entered via an alley staircase beneath a bar in River North, Three Dots and a Dash is a complement to Lost Lake rather than a competitor: it is larger, louder, more theatrical, and serves tiki cocktails that reward the late-night mood. The rum punch bowls for two or four are the correct order at this hour. The space holds 200 people and still manages to feel intimate in the booths along the back wall.
Eight seats. Reservations required. One of the smallest serious bars in the United States, operating inside the Chicago Athletic Association hotel on Michigan Avenue. The Milk Room serves rare and antique spirits as single pours or in cocktails, with a focus on American whiskey and aged rum from bottles that no longer exist in any commercial sense. The experience is quieter than anything else on this list, which makes it the right ending. For the full picture of Chicago's bar scene and world-class hidden gem bars, our dedicated guides cover the field.
The Chicago L covers Wicker Park (Blue Line), the West Loop (Green/Pink Line), and River North (Red Line). The Gold Coast is a 10-minute Uber from River North. Night buses cover the main corridors until 5am. Chicago winters are serious: if the itinerary runs from November through March, build in extra transit time and dress accordingly.
The Long Room on Irving Park Road in Lakeview is a neighborhood bar that does everything right and charges nothing extra for doing it: long wooden bar, good whiskey list, no attitude. It is 20 minutes from River North by L Train and worth the detour if the night ends early. For the complete guide to Chicago bars by neighbourhood and category, our one-night New York bar guide is the companion piece for the other great American bar city.
James Harlow covers New York, Chicago, Los Angeles, Las Vegas, Austin, and Nashville for barsforKings. He has spent fifteen years writing about American bar culture and maintains that Chicago's cocktail scene is the most underrated in the country by a significant margin.
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