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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.
Next door to the rowdy Diag Bar & Grill you'll find the serene 404 Wine Bar, a romantic spot filled with cozy nooks. The librarylike back room has ornate chandeliers, shelves lined with books, and dramatic oxblood walls. Grab a spot on the patio or near one of two fireplaces and enjoy a glass, flight, or bottle of wine accompanied by a cheese plate.
Done up in pretty Prussian blue with warm walnut accents, this wine bar/bottle shop channels calm vibes—and if you're still feeling keyed up, a pour or two from the Eurocentric wine list should do the job. Standard wine bar fare like cheese and charcuterie plus a few Spanish-inspired pintxos make up the small food menu.
This long-running cozy, candlelit bar is a romantic place for a date. It stocks more than 500 bottles of wine (at least 20 are available by the glass) plus ports, sherries, single-malt Scotches, a few microbrews, and a menu of small tasting entrées at reasonable prices. At $20 for 3 pours, the Monday evening self-guided blind tastings are a hit with neighborhood oenophiles.
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