The Best Bar in Chicago, Illinois

Background Illustration for Nightlife

Chicago's entertainment varies from loud and loose to sophisticated and sedate. You'll find classic Chicago corner bars in most neighborhoods, along with trendier alternatives like wine bars and lounges. The strains of blues and jazz provide much of the backbeat to the city's groove, and an alternative country scene is flourishing. As far as dancing is concerned, take your pick from cavernous clubs to smaller spots with DJs spinning dance tunes; there's everything from hip-hop to swing. Wicker Park/Bucktown and River North have the hottest nightlife, but prime spots are spread throughout the city.

Shows usually begin at 9 pm; cover charges generally range from $3 to $20, depending on the day of the week (Friday and Saturday nights are the most expensive). The list of blues and jazz clubs includes several South Side locations: be cautious about transportation here late at night, because some of these neighborhoods can be unsafe. Drive your own car or ask the bartender to call you a cab.

Toons Bar & Grill

Lakeview

At the far north end of the Southport Corridor sits this humble neighborhood watering hole with a wide range of offerings that somehow all work well together. It's a Kansas City-supporting sports bar, with a menu offering New Orleans-style po'boy sandwiches, while also serving some of the city's best deep-fried buffalo wings. Toons also has an impressive beer list for a casual sports-focused environment, with 20 taps serving drafts from the likes of Dovetail, Three Floyds, and Haymarket. Need a budget beverage? Order a Chicago Handshake: a pint of Old Style paired with a shot of Malört.

3857 N. Southport Ave., Chicago, IL, 60613, USA
773-935–1919

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