Editorial
Chicago is a drinking city in the original sense — a place where bars have always functioned as the central institution of neighbourhood life. Every block of Wicker Park has a dive that's been there since before the craft beer revolution. Every strip of River North has a cocktail program that could hold its own in New York or London. And the city has no shortage of what it always had: long bars, honest pours, and a crowd that treats conversation as a sport.
What makes a Chicago bar crawl different from most cities is the El — the elevated rail system that connects the city's bar neighbourhoods with surprising efficiency. Once you understand which line connects Wicker Park to the Loop and the Loop to Lincoln Park, you can cover serious ground without a cab. The three routes below are built around the El network.
Chicago's winters are brutal and bar queues outdoors are real. Download the Ventra app before your trip — it handles CTA fares and the Divvy bike-share network if you want to cross short distances in warmer months. Most good bars are cash-friendly but card-only spots are increasing.
Wicker Park is the spiritual heartland of Chicago bar culture. The intersection of Milwaukee, North, and Damen Avenues — known locally as "the six corners" — puts you within walking distance of a dozen bars that each represent something distinctive about the city. Start early and move fast; this route is about the collection, not the depth.
River North is Chicago's most concentrated strip of serious cocktail bars. The neighbourhood has attracted bartender talent from across the country, and a Friday night here can feel like touring a competition roster. Dress code is relaxed but the pace is elevated — these are bars where you slow down, read the menu, and commit.
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Chicago's most interesting bar growth of the last decade has happened in Logan Square and the stretches of Pilsen. This is where the chefs who couldn't afford River North rents opened restaurants, and where the bars followed. The route is longer geographically but the El handles the gap cleanly. Start at 8pm and expect to end near midnight.
The CTA El runs 24 hours and is the backbone of any Chicago bar crawl. The Blue Line connects O'Hare to Wicker Park, Logan Square, and the Loop. The Red Line runs from Howard to the South Side, stopping at Wrigleyville and downtown. The Pink Line connects Pilsen to the Loop. An all-day pass costs $10 and removes all transport decisions from your night.
Illinois state law requires bars to stop serving at 2am most nights. However, Chicago has a 4am liquor licence available to certain establishments — look for the "late-night" signs. The Green Mill, Longman & Eagle, and several other institutions hold 4am licences and are reliable options when the rest of the city closes. After 2am, expect queues.
Chicago's deep-dish pizza debate is legendary but irrelevant for bar crawlers. For bar food, the tavern-style thin crust (cut in squares, not slices) is what the locals eat: Piece Brewery in Wicker Park does exceptional thin crust and brews its own beer.
For more on Chicago's bar scene before you visit, read our full Chicago bar guide by neighbourhood and category. If sports bars are your focus, Chicago earns a place in our ranking of the world's best sports bar cities — the Cubs and Bears have generated a bar culture around fandom that few cities can match.
James has covered American bar culture for a decade, with a particular focus on cities that drink for real: Chicago, New Orleans, and Pittsburgh. He holds the conviction that the best bars in the US are in cities the food media ignores, and Chicago is his proof.