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Chicago Symphony Orchestra
- Home of the Chicago Symphony Orchestra
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- Classical Music/Opera
- Loop
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The Duke of Perth
- Scottish pub with huge whiskey selection
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- Pubs
- Lakeview/Wrigleyville
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Kingston Mines
- Down 'n' dirty blues
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- Jazz/Blues
- Lincoln Park
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Green Mill
- Swinging former speakeasy
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- Jazz/Blues
- Far North Side
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Webster's Wine Bar
- Fine wine bar
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- Wine Bars
- Lincoln Park
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Village Tap
- Roscoe Village's favorite hangout
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- Bars
- Lakeview/Wrigleyville
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Second City
- Famous theater and improv group
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- Comedy
- Lincoln Park
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Hopleaf
- Belgian beer lovers unite
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- Bars
- Far North Side
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Pops For Champagne
- Upscale River North Champagne Lounge and Jazz Club
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- Lounges
- Near North Side/River North
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Schubas Tavern
- Eclectic Local Dance and Drink
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- Venues
- Lakeview/Wrigleyville
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The Empty Bottle
- Only the bottle is empty
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- Venues
- Logan Square/Humboldt Park
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Sidetrack
- The Queen of gay bars
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- Bars
- Lakeview/Wrigleyville
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Juicy Wine Company
- Hip wine and cheese bar
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- Wine Bars
- Market District/River West
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The Violet Hour
- A Take-Note Bar
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- Lounges
- Wicker Park/Bucktown
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Simone's
- Laid-back eco-friendly bar & grill
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- Bars
- West Side/United Center/UIC
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Subterranean
- Multi-level music venue and lounge
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- Nightclubs
- Wicker Park/Bucktown
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Funky Buddha Lounge
- Diverse and funky club
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- Nightclubs
- Market District/River West
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The Underground
- An army of fun
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- Nightclubs
- Loop
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Smart Bar
- House Music Hot Spot
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- Nightclubs
- Lakeview/Wrigleyville
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The Hideout
- The best performance bar in the land
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- Bars
- Wicker Park/Bucktown
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ROOF
- Rooftop on the WIT
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- Lounges
- Loop
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In Fine Spirits
- Sophisticated local bar
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- Bars
- Far North Side
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Chicago Theatre
- Ornate, but tasteful theater
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- Theater
- Loop
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Steppenwolf Theatre Company
- World Renowned Actor's Group
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- Theater
- Lincoln Park
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Tiny Lounge
- Good things do come in small packages!
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- Bars
- Uptown/Lincoln Square
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