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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.
A longtime favorite, Roscoe's Tavern has a lot to offer its patrons, including a full all-day dining menu, jam-packed front bar, a dance floor, a pool table, an outdoor garden, DJs on the weekends, and a sidewalk café in warmer weather. When it's airing, Roscoe's also hosts Drag Race aftershows that regularly feature former contestants.
In business for over 40 years, this sprawling, multi-level club packs them in by the hundreds each weekend thanks to the fairly priced drinks (and extremely rare cover charges). Events include show tune singalongs, glow stick dance parties, lesbian-friendly Sapphic Saturdays, and even events for dog owners.
Of all the sports bars in Wrigleyville, Sluggers is perhaps the most famous. It's always packed before and after Cubs home games (and the ballplayers make occasional appearances in summer). Sluggers has a little bit of everything, including 40 TVs, fast- and slow-pitch batting cages, Skee-Ball, pool tables, air-hockey tables, electronic basketball, arcade games, and even a dueling-pianos show on the weekends.
This Ukrainian Village bar’s roots as a nightspot for local Polish immigrants can still be felt in its warm wood accents and retro backbar. Classic cocktails are the drink of choice; they pair perfectly with the warmth of the back patio’s brick fireplace.
Once you’ve found the alley entrance (hint: look for the red-roped line of people waiting outside), descend the glowing skull-lined stairs to reach this hip spot that’s an homage to the mid-century tiki craze. "Three Dots and a Dash" is an old-school, rum-based tiki cocktail that gets its name from the morse code for the letter "V" as in victory, as used in WWII. There are Pan-Pacific nibbles, like the shareable pu pu platter, to accompany the strong tropical cocktails adorned with flowers and served in tiki mugs.
At this favored no-frills tavern, locals and university students gather for beer, burgers, and Reuben sandwiches. Every second Sunday night, there's a free-form blues jam session followed by live jazz.
