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The Boss Bar

The Boss Bar
41.889891 -87.631411 420 N Clark St (at Hubbard St) River North, Chicago
Subway: Red to Grand(312) 527-1203 bossbarchicago.com
Sun–Fri 11am–4am; Sat 11am–5am
Average cocktail: $5
Guys, don’t even bother. This River North hangout has plenty of tables to nosh on a burger and a big, circular bar with plenty of stools to put down your pints. But after work, it’s crowded three-suits-deep with men trying to flirt with the gorgeous bartenders, so only a woman could get lucky here.

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Bars
  • A Spy Bar

    646 N Franklin St between Ontario and Erie Sts

  • B Club 720

    720 N Wells St between Huron and Superior Sts

  • C Lumen

    839 W Fulton Market between Green and Peoria Sts

  • D The Griffin Lounge

    326 W Chicago Ave between Franklin and Orleans Sts

  • E Shaw’s Crab House

    21 E Hubbard St between State St and Wabash Ave

  • F Bridge Bar

    315 N LaSalle St at the river

  • G Clark Street Ale House

    742 N Clark St between Superior St and Chicago Ave

  • H Epic Sky

    112 W Hubbard St between Clark and LaSalle Sts

  • I Untitled

    111 W Kinzie St between LaSalle and Clark Sts

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