Editorial
The new york vs chicago bars debate does not get enough attention. Chicago's bar scene has been quietly building one of the most interesting cocktail and craft beer ecosystems in the country, and it does it at price points that make New York feel like a premium tax on geography. We have been to both cities specifically to settle this question, and the honest answer requires nuance. Here is our category-by-category breakdown, with the specific bars that make each city's case.
New York has more top-tier cocktail bars than any other American city by a significant margin. The Lower East Side and East Village alone contain bars that would be the best in Chicago. But Chicago's top programs are not far behind, and the city's newer wave of cocktail bars in Logan Square and Pilsen is closing the gap faster than most New Yorkers have noticed.
This is not a close fight. Chicago has one of the best craft beer scenes in the country, anchored by a generation of breweries in Pilsen, Bridgeport, and Logan Square that produce some of the most interesting beers being made anywhere. New York has excellent craft beer, but Chicago's density of genuinely great brewery taprooms within a manageable geography puts it ahead.
A genuinely excellent cocktail in New York will cost $22 before tip and you will drink it standing up. A genuinely excellent cocktail in Chicago will cost $14 before tip and you will sit down to drink it. This difference compounds over the course of a proper bar-hopping night. Chicago's neighbourhoods also feel like neighbourhoods in a way that Manhattan's bar clusters often do not.
New York wins late night by the same logic it always does: the city does not close. Chicago's licensing laws are more relaxed than London's but less permissive than New York's. For sports bars, Chicago wins easily. The city's sports culture and the concentration of excellent sports bars around Wrigleyville and the United Center is something New York's more spread-out geography cannot match.
New York wins on the ceiling. The absolute best bars in New York are better than the absolute best bars in Chicago, and there are more of them. If you are chasing the finest cocktail you have ever had, go to New York. Chicago wins on value, craft beer, sports culture, and the kind of neighbourhood bar experience that does not require a credit card limit check. For a long weekend of genuinely excellent drinking without financial damage, Chicago is the right answer.
The cities deserve each other's respect. Any serious drinker should visit both at least once a year. The debate is worth having precisely because both cities have a case.
James covers American bar culture and has strong opinions about which Chicago neighbourhood wins on cocktail value per dollar. He visits both cities at least twice a year and considers the Malort shot a rite of passage.